The ACS Style Guide Effective Communication Of Scientific Information 3rd

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➤➤➤➤➤ The ACS Style Guide ➤➤➤➤➤ THIRD EDITION The ACS Style Guide Effective Communication of Scientiﬁc Information Anne M. Coghill Lorrin R. Garson Editors AMERICAN CHEMICAL SOCIETY Washington, DC OXFORD UNIVERSITY PRESS New York Oxford 2006 Oxford University Press Oxford New York Athens Auckland Bangkok Bogotá Buenos Aires Calcutta Cape Town Chennai Dar es Salaam Delhi Florence Hong Kong Istanbul Karachi Kuala Lumpur Madrid Melbourne Mexico City Mumbai Nairobi Paris São Paulo Singapore Taipei Tokyo Toronto Warsaw and associated companies in Berlin Idaban Copyright © 2006 by the American Chemical Society, Washington, DC Developed and distributed in partnership by the American Chemical Society and Oxford University Press Published by Oxford University Press, Inc. 198 Madison Avenue, New York, NY 10016 Oxford is a registered trademark of Oxford University Press All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without the prior permission of the American Chemical Society. Library of Congress Cataloging-in-Publication Data The ACS style guide : effective communication of scientiﬁc information.—3rd ed. / Anne M. Coghill [and] Lorrin R. Garson, editors. p. cm. Includes bibliographical references and index. ISBN-13: 978-0-8412-3999-9 (cloth : alk. paper) 1. Chemical literature—Authorship—Handbooks, manuals, etc. 2. Scientiﬁc literature— Authorship—Handbooks, manuals, etc. 3. English language—Style—Handbooks, manuals, etc. 4. Authorship—Style manuals. I. Coghill, Anne M. II. Garson, Lorrin R. III. American Chemical Society QD8.5.A25 2006 808'.06654—dc22 2006040668 1 3 5 7 9 8 6 4 2 Printed in the United States of America on acid-free paper ➤➤➤➤➤ Contents Foreword. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . vii Madeleine Jacobs Preface . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .ix Contributors. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .xiii Part 1. Scientiﬁc Communication 1. Ethics in Scientiﬁc Communication . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3 Gordon G. Hammes appendix 1-1: Ethical Guidelines to Publication of Chemical Research. . . . . . .11 2. Scientiﬁc Papers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17 3. The Editorial Process . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27 appendix 3-1: Proofreaders’ Marks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .36 4. Writing Style and Word Usage . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 5. Electronic Submission of Manuscripts Using Web-Based Systems. . . . . . . 59 Sarah C. Blendermann appendix 5-1: Online Submission at Selected Scientiﬁc Publishers and Research Grant Agencies . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .65 appendix 5-2: Key Features of Selected Online Submission Systems. . . . . . . . .68 6. Peer Review . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71 Barbara A. Booth 7. Copyright Basics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77 Karen S. Buehler, C. Arleen Courtney, and Eric S. Slater v vi ➤ The ACS Style Guide 8. Markup Languages and the Datument . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87 Peter Murray-Rust and Henry S. Rzepa appendix 8-1: The IUPAC International Chemical Identiﬁer, InChI . . . . . . . .101 Stephen R. Heller and Alan D. McNaught Part 2. Style Guidelines 9. Grammar, Punctuation, and Spelling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105 appendix 9-1: Recommended Spelling List . . . . . . . . . . . . . . . . . . . . . . . . . . . .129 10. Editorial Style . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 135 appendix 10-1: Computer and Internet Terms . . . . . . . . . . . . . . . . . . . . . . . . .163 appendix 10-2: Abbreviations, Acronyms, and Symbols. . . . . . . . . . . . . . . . . .169 11. Numbers, Mathematics, and Units of Measure . . . . . . . . . . . . . . . . . . . . . . . . 203 appendix 11-1: The International System of Units (SI) . . . . . . . . . . . . . . . . . . .228 12. Names and Numbers for Chemical Compounds . . . . . . . . . . . . . . . . . . . . . . 233 appendix 12-1: End-of-Line Hyphenation of Chemical Names . . . . . . . . . . . .247 appendix 12-2: Representation of Combinatorial Chemistry . . . . . . . . . . . . .250 Derek Maclean appendix 12-3: CAS Registry Numbers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .253 13. Conventions in Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 255 appendix 13-1: Symbols for Commonly Used Physical Quantities . . . . . . . . .277 appendix 13-2: The Crystallographic Information File. . . . . . . . . . . . . . . . . . .284 Frank H. Allen 14. References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 287 Janet S. Dodd, Leah Solla, and Paula M. Bérard appendix 14-1: CASSI Abbreviations for the 1000+ Most Commonly Cited Journals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .328 appendix 14-2: A Sample CASSI Entry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .340 15. Figures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 343 Betsy Kulamer 16. Tables. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 369 Betsy Kulamer 17. Chemical Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 375 Antony Williams 18. Selected Bibliography . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 385 Index. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .389 ➤➤➤➤➤ Foreword I fell in love with chemistry when I was 13. I fell in love with writing at the age of four when I learned to read. Indeed, my love of writing, and of writing well, was inspired by my love of reading. Perhaps that is true for all writers. Fortunately for me, I have been able to combine my love of chemistry with my love of reading and writing in a long career as a science communicator and journalist. Most recently, I served for eight and a half years as editor-in-chief of Chemical & Engineering News, the ﬂagship newsmagazine of the American Chemical Society. This gave me ample opportunity to read all of the stories in C&EN every week, not once but twice and sometimes three times; write weekly editorials and occasionally longer stories; and indulge my love of chemistry vicariously, as I read the scientiﬁc papers we highlighted in C&EN. But writing is not as easy as reading. Writing and communicating take a great deal of skill and effort. One of my favorite quotations on the subject of writing comes from the novelist John Irving, who observed in The World According to Garp that a writer never reads for fun. It’s true for me. When I read a sentence that is well crafted or even better, a scientiﬁc paper that is full of well-crafted sentences, I am always trying to ﬁgure out how the author managed to express a complicated idea with such ease and grace. The goal of The ACS Style Guide is to help authors and editors achieve that ease and grace in all of their communications. To my mind, there’s no reason why scientiﬁc papers should not be as easy to read as a good novel. That’s a tall order, I realize, but if you read through this style guide, you will have all the tools Copyright 2006 American Chemical Society vii viii ➤ The ACS Style Guide you need to help you achieve that goal. It’s a wonderful reference book that I keep on my bookshelf and refer to often. I hope you will as well. Madeleine Jacobs Executive Director and Chief Executive Ofﬁcer American Chemical Society ➤➤➤➤➤ Preface S ince publication of the second edition of The ACS Style Guide in 1997, much has changed in the world of scientiﬁc communication—and yet, many things remain the same. During the past eight years, electronic dissemination of scientiﬁc, technical, and medical (STM) information has come to fruition. In chemistry, both the American Chemical Society and the Royal Society of Chemistry have made their scientiﬁc journals available on the World Wide Web and have digitized their respective publications back to the 19th century. Commercial publishers, who publish most of the world’s chemical information, have likewise made their publications available on the Web. Publications in other scientiﬁc disciplines, engineering, and medicine have also taken this digital pathway. Whereas traditional journals continue to be printed and used, electronic delivery has greatly expanded the availability and reading of STM information far beyond what could have ever been envisioned with paper journals. Most manuscripts are now written with de facto standard word-processing software and adhere to formats developed for electronic creation and processing. Most manuscripts are submitted electronically, principally via the Internet on the Web. Communications among editors, reviewers, and authors are now largely electronic, as is communication between editors and production facilities and printers. Regardless of the mode of information creation and delivery, the necessity for accurate information communicated in a clear, unambiguous manner, coupled with the ethical behavior of all participants, remains the same. As Janet Dodd wrote in the preface to the second edition, “In the midst of all this change, the comforting thought is that one goal of authors and editors has not changed: to communicate information in the most understandable and expedient fashion in Copyright 2006 American Chemical Society ix x ➤ The ACS Style Guide publications of the highest quality. To accomplish that goal, we need guidelines. This book is intended to guide and answer questions for authors and editors, to save them time, and to ensure clarity and consistency.” Third Edition The third edition aims to continue such guidance while broadening the scope of the book to accommodate changes in technology and the homogenization of international scientiﬁc publishing. New topics in the third edition include chapters on • ethics in scientiﬁc communication; • submitting manuscripts via the Web; • preparing and submitting publisher-ready ﬁgures, tables, and chemical structures, including information about various software programs to create artwork; • formatting manuscript references to electronic resources and information on reference-management software; and • markup languages, in anticipation of the classiﬁcation and capture of scientiﬁc information in yet-to-be-deﬁned structures. The chapters on peer review, copyright, the editorial process, and writing style and word choice have been extensively rewritten. Although language certainly evolves with time, there have not been substantial changes in English during the past seven years. The chapters on grammar, punctuation, spelling, and conventions in chemistry remain largely the same as in the second edition. The use of typefaces, superscripts and subscripts, Greek letters, special symbols, numbers, mathematics, units of measure, and names and numbers for chemical compounds are generally unchanged, although some of the existing rules have been clariﬁed. Some new rules and examples have been added to reﬂect new ﬁelds in chemistry, such as combinatorial chemistry and chemical biology. In all chapters, errors have been corrected (and almost certainly new errors inadvertently introduced!), and some changes have been made to reﬂect changes in practice, particularly as related to electronic issues. Several features have been added to the third edition to improve the readers’ ease of use: • The contents are reorganized into two sections. The ﬁrst section, “Scientiﬁc Communication”, contains chapters giving readers information on broad topics such as ethics in scientiﬁc communication, writing style and word usage, and submission of manuscripts using a Web-based system. The second section, “Style Guidelines”, contains chapters that give speciﬁc rules and examples. For instance, in these chapters readers will ﬁnd infor- Preface ➤ xi mation on such topics as grammar, punctuation, and spelling; formatting numbers and specialized chemical conventions; when to use special typefaces; how to format references; and how to create ﬁgures, tables, and chemical structures. • Throughout the book, the arrowlike icon (➤) precedes rules. These rules may refer to grammar, word usage, or punctuation rules. Also, the icon may precede rules for creating publisher-ready artwork, rules about styling chemical terms, or rules about formatting names and chemical compounds. Examples are given under the rule to further illustrate it. • Attention is drawn to particularly important topics by the use of reminders and boxes. Reminders are bounded by horizontal rules and are identiﬁed with a small pencil icon (✐); they contain a brief note on a single topic. Boxes are numbered sequentially within each chapter and contain more extensive information on a speciﬁc topic. Reminders and boxes that contain ACS-speciﬁc information are identiﬁed by a small ACS phoenix icon ( ). We believe that identiﬁcation of these key issues in this manner will be helpful to readers. Because of the desire on the part of the publisher to increase the use of the third edition of The ACS Style Guide, it is being made available on the World Wide Web. It is expected that periodic updates will be made to the electronic edition, which would not be feasible for the printed version. Additionally, if readers would like to request clariﬁcation of rules, they may do so by contacting the publisher at styleguide@acs.org or by addressing correspondence to The ACS Style Guide, Books Department, American Chemical Society, 1155 Sixteenth Street, NW, Washington, DC 20036. Although The ACS Style Guide is written with an emphasis on chemistry and, to some extent, a focus on ACS journals, we believe that it has wide applicability to the sciences, engineering, medicine, and other disciplines. Chemistry is a mature science that cuts across virtually all basic and applied sciences. Science in its broadest sense has always been an international activity. However, there is an increasing trend toward internationalization of scientiﬁc communication. For example, for the past several years, the majority of authors publishing in ACS journals reside outside North America. English has become the lingua franca of science in the same way that French once was the international language of diplomacy and commerce. The venerated Beilsteins Handbuch der Organischen Chemie has been published in English for a number of years. The prestigious journal Angewandte Chemie: International Edition in English conveys internationalization and the English language merely by its title. The premier publications Science and Nature, both published in English, have broad international authorship and readership. We believe that The ACS Style Guide will be a useful tool for the international scientiﬁc community using this common language. xii ➤ The ACS Style Guide Acknowledgments The editors would like to thank all the chapter authors and reviewers who contributed to this project. In particular, we would like to thank our colleagues in Columbus who provided assistance with all the style guidelines in the book, namely, Toddmichael Janiszewski, Diane Needham, “Ram” Ramaswami Ravi, Teresa Schleifer, and Joe Yurvati. A special thank you goes to Betsy Kulamer and Paula M. Bérard for their skilled editorial efforts. We certainly could not have completed this project without their capable assistance. We want to thank Sue Nedrow, who prepared an in-depth index that we think will be very useful to the readers. We also wish to express our appreciation to Bob Hauserman at the ACS for his suggestions and help. Finally, we would like to express our indebtedness to Janet S. Dodd, who edited the ﬁrst and second editions of The ACS Style Guide. Janet was more than the editor; she wrote much of the ﬁrst two editions. Her contributions persist in the third edition. Anne M. Coghill Lorrin R. Garson April 2006 ➤➤➤➤➤ Contributors Frank H. Allen Gordon G. Hammes Cambridge Crystallographic Data Centre Department of Biochemistry Duke University Paula M. Bérard Chattanooga, Tennessee Stephen R. Heller Sarah C. Blendermann Division of Chemical Nomenclature and Structure Representation International Union of Pure and Applied Chemistry ACS Publications Division, Ofﬁce of Journal Support Services American Chemical Society Betsy Kulamer Barbara A. Booth Kulamer Publishing Services Department of Civil and Environmental Engineering University of Iowa Derek Maclean Karen S. Buehler Alan D. McNaught ACS Publications Division, Copyright Ofﬁce American Chemical Society C. Arleen Courtney Division of Chemical Nomenclature and Structure Representation International Union of Pure and Applied Chemistry ACS Publications Division, Copyright Ofﬁce American Chemical Society Peter Murray-Rust Janet S. Dodd Chemical & Engineering News American Chemical Society KAI Pharmaceuticals Unilever Centre for Molecular Informatics Department of Chemistry University of Cambridge Copyright 2006 American Chemical Society xiii xiv ➤ The ACS Style Guide Henry S. Rzepa Leah Solla Department of Chemistry Imperial College London Physical Sciences Library Cornell University Eric S. Slater Antony Williams ACS Publications Division, Copyright Ofﬁce American Chemical Society Advanced Chemistry Development, Inc. ➤➤➤➤➤ Part 1 Scientiﬁc Communication ➤➤➤➤➤ CHAPTER 1 Ethics in Scientiﬁc Publication Gordon G. Hammes T he principles that govern the ethics of scientiﬁc publication are no different than for any other endeavor: complete and accurate reporting and appropriate attribution to the contributions of others. However, as always, “the devil is in the details.” The ethical responsibilities of authors and reviewers are sufﬁciently important and complex that the editors of the American Chemical Society journals have developed a detailed document outlining these responsibilities. (This document, “Ethical Guidelines to Publication of Chemical Research” is presented in Appendix 1-1.) The purpose of this chapter is not to duplicate this document, but rather to discuss some of the important underlying principles and situations that often arise. Scientiﬁc research, perhaps more than most professions, crucially depends on the integrity of the investigators. Most research consists of a series of complex experiments or theoretical calculations that cannot (or will not) be duplicated easily elsewhere. Moreover, it is usually extremely difﬁcult to determine in detail if the results are correct and can be trusted. Published results generally are accepted at face value. Very often related work eventually may be done by others that tests the results, so that checks and balances exist within the system. This is usually a long process, however, and the advance of science may be signiﬁcantly delayed if published results are not correct. The bottom line is that we depend on the integrity of the investigators reporting the results. We assume that the description of the work is accurate and honest unless proven otherwise. This places a considerable burden on the authors to ensure that the system works. Research is by its nature exploratory, and honest mistakes may occur. Errors due to human fallibility are unfortunate, but not unethical. Research inevitably Copyright 2006 American Chemical Society 3 4 ➤ The ACS Style Guide pushes the boundaries of existing methodology and theory, so that errors in judgment and interpretation are bound to occur. This is a normal part of the scientiﬁc establishment. An often-quoted adage is that the only way never to make a mistake in print is never to publish. Errors due to carelessness or haste are poor science; they represent irresponsible, but not unethical, behavior. Errors due to fabrication and falsiﬁcation clearly are unethical and cannot be tolerated under any circumstances. Breakdowns in the system that are not honest mistakes have occurred; some examples are published by the Ofﬁce of Research Integrity of the U.S. Department of Health and Human Services at http://ori. dhhs.gov. Fortunately, these breakdowns seem to be relatively few. It is the responsibility of each author to ensure the quality and integrity of the research that is reported. The ethical principles governing the conduct of science should be well understood by all participants. This chapter considers only some aspects of this subject. An excellent introductory publication is available online from the National Academy of Sciences; see “On Being a Scientist: Responsible Conduct in Research” at http://www.nap.edu/readingroom/books/obas/. When To Publish: Signiﬁcance and Timeliness When is it time to publish? Research is open-ended, so the answer to this question is not always obvious and requires authors to balance signiﬁcance and timeliness to arrive at a high-quality manuscript. ✐ Reminder: Research should be published in a timely manner when enough work has been done to yield signiﬁcant results. Researchers must decide when enough work has been done to make a signiﬁcant contribution to a ﬁeld. “Signiﬁcant” is in the eye of the beholder, and sometimes reviewers and authors will differ markedly with regard to this judgment. The give and take between authors and reviewers is part of the normal process of science and undoubtedly improves the quality of published work. Clearly neither science nor scientiﬁc publishing are enhanced by a continual stream of short, incomplete descriptions of a research project. A publication should describe a project that is complete unto itself and represents a true advance in the ﬁeld. (An exception to this rule occurs when a very unusual result is obtained that is of great interest and signiﬁcance—in this case, publication as a preliminary note may be justiﬁed.) Scientists also have an obligation to publish their research results in a timely manner. Unpublished research results constitute research not done in the eyes of other scientists. Unnecessary delays can result in duplication of efforts and may hinder the advancement of science. Under no circumstances should a manuscript Chapter 1: Ethics in Scientiﬁc Publication ➤ 5 be submitted and then held up in the revision or page proof stage for reasons not directly related to the research—for example, because of patent considerations. Given the “publish or perish” mentality that sometimes exists, researchers may be tempted to maximize their number of publications by publishing many short, somewhat repetitive research reports. This practice serves no useful purpose for science or the investigator. In truth, the reputation of an investigator is ultimately determined by the quality of research done over an extended time. Beginning independent investigators are often told that a research reputation can be thought of as a product of quantity times quality of published work. If only one publication appears every 10 years, they may be advised, it had better be a good one. On the other hand, a large number of low-quality publications is not of beneﬁt to the individual or the profession. Investigators may be tempted to publish the same material, or material only slightly different, multiple times. This practice is unethical. The manuscript should clearly describe prior work that has been done by the authors. It is the obligation of the corresponding author to inform the journal editor of any related manuscripts that have been submitted and/or published elsewhere, including preliminary communications and symposium volumes. There are no exceptions. Moreover, although the review process can be lengthy, under no circumstances should a manuscript be submitted simultaneously to multiple journals. What To Publish: Full Disclosure Unfortunately, because of space limitations, the trend in publishing research results is to provide less and less detail. Although brevity is admirable, it is important that the results be described fully and accurately. Moreover, all of the results should be reported, not just those supporting the underlying hypotheses of the research. If necessary, most journals allow the possibility of submitting supporting documentation as supplementary information. Although this material does not appear in the printed version, it is readily available online. The rule of thumb is that sufﬁcient information should be provided so that other investigators could repeat the experiments if they so desired. The necessity for providing sufﬁcient detail has to be balanced with the need to conserve publication space. As might be expected, considerable variation exists in practice as to what this entails. The manuscript review process plays a tempering role, balancing these two factors. Representative data and/or calculations are an important part of any scientiﬁc presentation. Obviously, not all of the data, derivations, and calculations can be presented. It is acceptable for the “typical data and/or calculations” that are presented to be among the best, but all the data should be included in the analyses. The reproducibility of the results is an implicit assumption for published work. However, ﬁrst-rate research often involves difﬁcult measurements at the edge of existing methodology, and the difference between signal and noise may 6 ➤ The ACS Style Guide be hard to distinguish. It is acceptable to report results for which this is the case, as long as the appropriate qualiﬁcations are clearly stated. A critical assessment of the research should be made by the investigator, including an error analysis. No one should be more critical of the research that is reported than the authors. Who Are Authors? Generally speaking, all authors of a publication should have made signiﬁcant and substantial intellectual contributions to the work being reported. Unfortunately, this principle is often breached, as evidenced by manuscripts with tens, even hundreds, of authors. Some laboratories put the names of everyone in the laboratory on the published work, and some individuals put their names on every publication coming out of a laboratory, even if their participation was only nominal. If a colleague prepared buffers or did routine computer programming, these contributions should be acknowledged, but they are not sufﬁcient contributions for authorship. General discussion with colleagues or within research groups is rarely sufﬁcient for inclusion in authorship. Despite some arbitrariness in deﬁning what constitutes a signiﬁcant intellectual contribution, the guiding ethical principle is clear and should be adhered to. Usually the question of authorship can be decided by discussion among the participants in the research. Occasionally, a third party may be required to adjudicate this issue. In any event, this matter should be fully resolved before submission of a manuscript. A question that often arises concerns the order of the authors’ names. This is not really an ethical issue, and practice varies from place to place. Most often the ﬁrst author is assumed to have made the major contribution to the work, and the senior and/or corresponding author is listed last. However, many variations to this theme exist, such as putting the authors in alphabetical order. In some cases, the speciﬁc contributions of each author are described. Ideally, the order of authorship should be decided amicably among the authors, but perceptions sometimes differ between the individuals involved. Authors should not become obsessed with this matter. Ultimately, a researcher’s scientiﬁc reputation rests on the totality of publications and the signiﬁcance of contributions to the ﬁeld. It is often said that all authors are responsible for the entire content of a manuscript. This is a meritorious ideal, but unrealistic. Most manuscripts have multiple authors, and very often, a single author is responsible for only a portion of the work being presented. For example, the manuscript may contain a crystal structure, determined by an expert crystallographer; spectral data, determined by an expert spectroscopist; kinetic data, determined by an expert kineticist; etc. In cases such as this, a single author cannot be held responsible for all of the results presented. A more realistic assessment of what authorship implies is that each author should have read the manuscript carefully and understood the ﬁndings, but the technical responsibility is only for the area in which a given author Chapter 1: Ethics in Scientiﬁc Publication ➤ 7 has the appropriate expertise. The responsibility of the corresponding author is to ensure that all authors have approved the manuscript before submission and for all subsequent revisions. What Went Before: Attribution and Context Every scientiﬁc publication must include the proper attribution of the contributions of others by appropriate referencing and the placement of results within the context of the research ﬁeld. Referencing is a complex subject (see Chapter 14 of this volume). Every reference in the ﬁeld cannot be cited, or the reference list would become intolerably long. However, important ideas and experiments must be cited. The introduction and discussion sections of a manuscript should be absolutely clear as to what the work of others has contributed to the research being reported. If data are presented that have been previously published, this should be clearly indicated. Direct quotations of more than a few words should be indicated by quotation marks and referenced. Paraphrases of quotations also should be referenced. Plagiarism—taking the writings or ideas of another and passing them off as one’s own—of any type represents unethical conduct. Occasionally, the attribution of an idea or fact may be to a “private communication” of a colleague or fellow scientist. In such cases, permission must be obtained from the individual in question before the citation is made. Reference to unpublished material should be avoided if possible because it generally will not be available to interested readers. ✐ Reminder: Every manuscript must reference the contributions of others and place results in the context of the research ﬁeld. The results and conclusions sections of a manuscript should be placed within the context of the research area. What was known before the research being presented? What has this research contributed that is new and signiﬁcant? It should also be clear what conclusions are based on the work presented and which are speculations. It is appropriate to speculate—in fact, this is a stimulus to the ﬁeld—as long as speculations are labeled as such. In this regard, the values and judgments of the authors and current thinking appropriately come into play. Not all attributions to previous work cite supportive data. In some cases, results under discussion may differ from previous work, or authors may make critical comments about earlier research. Differences between the work reported and previous results must be discussed and reconciled. Criticism of previous work should be presented carefully and objectively, in terms of the facts only. This is part of normal scientiﬁc discourse. Criticism should never be directed at 8 ➤ The ACS Style Guide individuals or laboratories; it is essential to consider only the facts that have been presented. Acknowledgments should be made to people who have assisted in the project, but not sufﬁciently for authorship, and to sponsoring agencies. It is also imperative to acknowledge potential conﬂicts of interest that may exist. For example, if the research being reported concerns drug XYZ and one of the authors has a substantial ﬁnancial interest in a company that makes drug XYZ or is conducting clinical trials with drug XYZ, these facts should be explicitly stated. What Next: After Publication An author’s obligations do not stop with publication. If errors are found in the published work, they should be corrected with the publication of errata. If other investigators request more information or more complete data, the requests should be fulﬁlled without delay. A trickier issue concerns the distribution of special materials used in the research. The rule of thumb is that the authors should be willing to provide others with a reasonable supply of special materials that have been used in the research. However, some common sense should be applied to this rule. For example, if two years have been spent cloning a speciﬁc protein and it will be used in future research, it is unreasonable to expect researchers to give this clone to competitors who are planning similar experiments. Similarly, if a complex substance has been synthesized and only a small supply is available, it would be unreasonable to expect the material to be given away. However, the publication should provide sufﬁcient detail so that other researchers can develop the clone themselves or synthesize the compound in question. Although ethical behavior in this area is not always clear, the general rule is that all aspects of the research should be fully disclosed and reasonable assistance should be given to other researchers. Progress in science depends greatly on open communication and cooperation. Obligations of a Reviewer Scientiﬁc discourse depends on critical review of manuscripts before publication. (Peer review—including ethical considerations—is discussed in greater detail in Chapter 6 of this volume.) The primary obligation of reviewers is to provide a rational, objective review of the science. This requires a careful reading of the manuscript and a careful preparation of the review. The review process is anonymous for most journals, but this does not mean that the reviewer has free rein to criticize. Any criticism must be logically and objectively delineated, and it should never be directed at the authors personally. Reviewers also should place the work within the context of the ﬁeld: is it a major contribution, minor contri- Chapter 1: Ethics in Scientiﬁc Publication ➤ 9 bution, or an insufﬁcient contribution to merit publication? Promptness in carrying out reviews is important and an ethical issue. Delaying a publication could be costly to an author, especially in a competitive ﬁeld. The usual golden rule applies: review with the care and speed you expect for your own manuscripts. If a reviewer cannot meet a deadline, he or she should inform the publisher as soon as possible. Manuscripts sent to reviewers are conﬁdential documents. Unfortunately, a signiﬁcant number of reviewers interpret the word “conﬁdential” incorrectly. Conﬁdential does not mean that reviewers can expand the scope of conﬁdentiality, for example, within their research groups, by including a few colleagues, and so on. Conﬁdential documents should not be shared or discussed with anybody without the explicit consent of the journal editor, the editorial board member handling the manuscript, or both. For example, senior investigators sometimes have graduate students or postdoctorals review manuscripts. This is acceptable only if the permission of the editor or editorial board member has been obtained. In some cases, a reviewer may discuss the results with a colleague; this also is forbidden if permission has not been obtained. Although breaches of conﬁdentiality do not usually do any harm and are not intended to do so, they are unethical and should be avoided. If reviewers have conﬂicts of interest with regard to a given manuscript, the manuscript should be returned as quickly as possible to the editor. Conﬂicts of interest vary. Perhaps similar research is being carried out in the reviewer’s laboratory, or the reviewer may be privy to conﬁdential information that conﬂicts with the results reported. Conﬂicts of interest can be more personal in nature: perhaps a reviewer has had personal difﬁculties with or is a close friend of one of the authors. When in doubt, the usual rule is not to review or read the manuscript. If you are unsure, ask the editor handling the manuscript. The editor may want your expert opinion even if some level of apparent conﬂict exists. Finally, the results in a manuscript under review cannot be quoted or incorporated into a reviewer’s own research program. After the work is published, a reviewer may use the ideas and data presented (with proper attribution), but the reviewer should not do so based on the review process. Such behavior is akin to insider trading in the purchase of stocks. Although a prison term is unlikely for this breach of conduct, the ethical principle is quite clear. Obligations as a Reader Not all errors are found before publication by authors and reviewers; some are discovered by readers. If the errors involve serious misinterpretation or misquotation of the literature, the most straightforward procedure is to contact the author(s) directly. If this is awkward, the editor can be informed. It is not worthwhile, however, to create a fuss for nonsubstantive errors. Self-serving com- 10 ➤ The ACS Style Guide plaints, such as not quoting the reader’s own work enough, seldom have much credibility. In rare situations, a scientist may have evidence that published material contains falsiﬁcation, fabrication, or plagiarism. It is the obligation of every scientist to report such cases immediately to the editor of the journal. Institutions receiving ﬁnancial support from the National Institutes of Health and the National Science Foundation are required to have mechanisms in place to investigate such occurrences, and direct reporting to the appropriate institutional ofﬁce may be more expedient. Accusations must be supported by fact, not suspicions, because academic misconduct is a serious matter with career-threatening implications. Unpleasant as this situation may be, it should not be ignored. For the Health of Research This chapter has emphasized the global ethics of the publication process. Ethics are not complicated, and the practices and rules are mainly common sense. Adherence to ethical standards in research and publication is not optional; rather, it is essential for the health of scientiﬁc research. ➤➤➤➤➤ APPENDIX 1-1 Ethical Guidelines to Publication of Chemical Research The guidelines embodied in this document were revised by the Editors of the Publications Division of the American Chemical Society in January 2000. Preface The American Chemical Society serves the chemistry profession and society at large in many ways, among them by publishing journals which present the results of scientiﬁc and engineering research. Every editor of a Society journal has the responsibility to establish and maintain guidelines for selecting and accepting papers submitted to that journal. In the main, these guidelines derive from the Society’s deﬁnition of the scope of the journal and from the editor’s perception of standards of quality for scientiﬁc work and its presentation. An essential feature of a profession is the acceptance by its members of a code that outlines desirable behavior and speciﬁes obligations of members to each other and to the public. Such a code derives from a desire to maximize perceived beneﬁts to society and to the profession as a whole and to limit actions that might serve the narrow self-interests of individuals. The advancement of science requires the sharing of knowledge between individuals, even though doing so may sometimes entail forgoing some immediate personal advantage. With these thoughts in mind, the editors of journals published by the American Chemical Society now present a set of ethical guidelines for persons engaged in the publication of chemical research, speciﬁcally, for editors, authors, and manuscript reviewers. These guidelines are offered not in the sense that there is any immediate crisis in ethical behavior, but rather from a conviction that the observance of high ethical standards is so vital to the whole scientiﬁc enterprise that a deﬁnition of those standards should be brought to the attention of all concerned. We believe that most of the guidelines now offered are already understood and subscribed to by the majority of experienced research chemists. They may, however, be of substantial help to those who are relatively new to research. Even The ethical guidelines are also available in their most recent version on the Web at https:// paragon.acs.org. 11 12 ➤ The ACS Style Guide well-established scientists may appreciate an opportunity to review matters so signiﬁcant to the practice of science. Guidelines A. Ethical Obligations of Editors of Scientiﬁc Journals 1. An editor should give unbiased consideration to all manuscripts offered for publication, judging each on its merits without regard to race, religion, nationality, sex, seniority, or institutional afﬁliation of the author(s). An editor may, however, take into account relationships of a manuscript immediately under consideration to others previously or concurrently offered by the same author(s). 2. An editor should consider manuscripts submitted for publication with all reasonable speed. 3. The sole responsibility for acceptance or rejection of a manuscript rests with the editor. Responsible and prudent exercise of this duty normally requires that the editor seek advice from reviewers, chosen for their expertise and good judgment, as to the quality and reliability of manuscripts submitted for publication. However, manuscripts may be rejected without review if considered inappropriate for the journal. 4. The editor and members of the editor’s staff should not disclose any information about a manuscript under consideration to anyone other than those from whom professional advice is sought. (However, an editor who solicits, or otherwise arranges beforehand, the submission of manuscripts may need to disclose to a prospective author the fact that a relevant manuscript by another author has been received or is in preparation.) After a decision has been made about a manuscript, the editor and members of the editor’s staff may disclose or publish manuscript titles and authors’ names of papers that have been accepted for publication, but no more than that unless the author’s permission has been obtained. 5. An editor should respect the intellectual independence of authors. 6. Editorial responsibility and authority for any manuscript authored by an editor and submitted to the editor’s journal should be delegated to some other qualiﬁed person, such as another editor of that journal or a member of its Editorial Advisory Board. Editorial consideration of the manuscript in any way or form by the author-editor would constitute a conﬂict of interest, and is therefore improper. 7. Unpublished information, arguments, or interpretations disclosed in a submitted manuscript should not be used in an editor’s own research except with the consent of the author. However, if such information indicates that some of the editor’s own research is unlikely to be proﬁtable, the editor could Chapter 1: Ethics in Scientiﬁc Publication ➤ 13 ethically discontinue the work. When a manuscript is so closely related to the current or past research of an editor as to create a conﬂict of interest, the editor should arrange for some other qualiﬁed person to take editorial responsibility for that manuscript. In some cases, it may be appropriate to tell an author about the editor’s research and plans in that area. 8. If an editor is presented with convincing evidence that the main substance or conclusions of a report published in an editor’s journal are erroneous, the editor should facilitate publication of an appropriate report pointing out the error and, if possible, correcting it. The report may be written by the person who discovered the error or by an original author. 9. An author may request that the editor not use certain reviewers in consideration of a manuscript. However, the editor may decide to use one or more of these reviewers, if the editor feels their opinions are important in the fair consideration of a manuscript. This might be the case, for example, when a manuscript seriously disagrees with the previous work of a potential reviewer. B. Ethical Obligations of Authors 1. An author’s central obligation is to present an accurate account of the research performed as well as an objective discussion of its signiﬁcance. 2. An author should recognize that journal space is a precious resource created at considerable cost. An author therefore has an obligation to use it wisely and economically. 3. A primary research report should contain sufﬁcient detail and reference to public sources of information to permit the author’s peers to repeat the work. When requested, the authors should make a reasonable effort to provide samples of unusual materials unavailable elsewhere, such as clones, microorganism strains, antibodies, etc., to other researchers, with appropriate material transfer agreements to restrict the ﬁeld of use of the materials so as to protect the legitimate interests of the authors. 4. An author should cite those publications that have been inﬂuential in determining the nature of the reported work and that will guide the reader quickly to the earlier work that is essential for understanding the present investigation. Except in a review, citation of work that will not be referred to in the reported research should be minimized. An author is obligated to perform a literature search to ﬁnd, and then cite, the original publications that describe closely related work. For critical materials used in the work, proper citation to sources should also be made when these were supplied by a nonauthor. 5. Any unusual hazards inherent in the chemicals, equipment, or procedures used in an investigation should be clearly identiﬁed in a manuscript reporting the work. 6. Fragmentation of research reports should be avoided. A scientist who has done extensive work on a system or group of related systems should organize 14 ➤ The ACS Style Guide publication so that each report gives a well-rounded account of a particular aspect of the general study. Fragmentation consumes journal space excessively and unduly complicates literature searches. The convenience of readers is served if reports on related studies are published in the same journal, or in a small number of journals. 7. In submitting a manuscript for publication, an author should inform the editor of related manuscripts that the author has under editorial consideration or in press. Copies of those manuscripts should be supplied to the editor, and the relationships of such manuscripts to the one submitted should be indicated. 8. It is improper for an author to submit manuscripts describing essentially the same research to more than one journal of primary publication, unless it is a resubmission of a manuscript rejected for or withdrawn from publication. It is generally permissible to submit a manuscript for a full paper expanding on a previously published brief preliminary account (a “communication” or “letter”) of the same work. However, at the time of submission, the editor should be made aware of the earlier communication, and the preliminary communication should be cited in the manuscript. 9. An author should identify the source of all information quoted or offered, except that which is common knowledge. Information obtained privately, as in conversation, correspondence, or discussion with third parties, should not be used or reported in the author’s work without explicit permission from the investigator with whom the information originated. Information obtained in the course of conﬁdential services, such as refereeing manuscripts or grant applications, should be treated similarly. 10. An experimental or theoretical study may sometimes justify criticism, even severe criticism, of the work of another scientist. When appropriate, such criticism may be offered in published papers. However, in no case is personal criticism considered to be appropriate. 11. The coauthors of a paper should be all those persons who have made signiﬁcant scientiﬁc contributions to the work reported and who share responsibility and accountability for the results. Other contributions should be indicated in a footnote or an “Acknowledgments” section. An administrative relationship to the investigation does not of itself qualify a person for coauthorship (but occasionally it may be appropriate to acknowledge major administrative assistance). Deceased persons who meet the criterion for inclusion as coauthors should be so included, with a footnote reporting date of death. No ﬁctitious name should be listed as an author or coauthor. The author who submits a manuscript for publication accepts the responsibility of having included as coauthors all persons appropriate and none inappropriate. The submitting author should have sent each living coauthor a draft copy of the manuscript and have obtained the coauthor’s assent to coauthorship of it. Chapter 1: Ethics in Scientiﬁc Publication ➤ 15 12. The authors should reveal to the editor any potential conﬂict of interest, e.g., a consulting or ﬁnancial interest in a company, that might be affected by publication of the results contained in a manuscript. The authors should ensure that no contractual relations or proprietary considerations exist that would affect the publication of information in a submitted manuscript. C. Ethical Obligations of Reviewers of Manuscripts 1. Inasmuch as the reviewing of manuscripts is an essential step in the publication process, and therefore in the operation of the scientiﬁc method, every scientist has an obligation to do a fair share of reviewing. 2. A chosen reviewer who feels inadequately qualiﬁed to judge the research reported in a manuscript should return it promptly to the editor. 3. A reviewer (or referee) of a manuscript should judge objectively the quality of the manuscript, of its experimental and theoretical work, of its interpretations and its exposition, with due regard to the maintenance of high scientiﬁc and literary standards. A reviewer should respect the intellectual independence of the authors. 4. A reviewer should be sensitive to the appearance of a conﬂict of interest when the manuscript under review is closely related to the reviewer’s work in progress or published. If in doubt, the reviewer should return the manuscript promptly without review, advising the editor of the conﬂict of interest or bias. Alternatively, the reviewer may wish to furnish a signed review stating the reviewer’s interest in the work, with the understanding that it may, at the editor’s discretion, be transmitted to the author. 5. A reviewer should not evaluate a manuscript authored or coauthored by a person with whom the reviewer has a personal or professional connection if the relationship would bias judgment of the manuscript. 6. A reviewer should treat a manuscript sent for review as a conﬁdential document. It should neither be shown to nor discussed with others except, in special cases, to persons from whom speciﬁc advice may be sought; in that event, the identities of those consulted should be disclosed to the editor. 7. Reviewers should explain and support their judgments adequately so that editors and authors may understand the basis of their comments. Any statement that an observation, derivation, or argument had been previously reported should be accompanied by the relevant citation. Unsupported assertions by reviewers (or by authors in rebuttal) are of little value and should be avoided. 8. A reviewer should be alert to failure of authors to cite relevant work by other scientists, bearing in mind that complaints that the reviewer’s own research was insufﬁciently cited may seem self-serving. A reviewer should call to the editor’s attention any substantial similarity between the manuscript under 16 ➤ The ACS Style Guide consideration and any published paper or any manuscript submitted concurrently to another journal. 9. A reviewer should act promptly, submitting a report in a timely manner. Should a reviewer receive a manuscript at a time when circumstances preclude prompt attention to it, the unreviewed manuscript should be returned immediately to the editor. Alternatively, the reviewer might notify the editor of probable delays and propose a revised review date. 10. Reviewers should not use or disclose unpublished information, arguments, or interpretations contained in a manuscript under consideration, except with the consent of the author. If this information indicates that some of the reviewer’s work is unlikely to be proﬁtable, the reviewer, however, could ethically discontinue the work. In some cases, it may be appropriate for the reviewer to write the author, with copy to the editor, about the reviewer’s research and plans in that area. 11. The review of a submitted manuscript may sometimes justify criticism, even severe criticism, from a reviewer. When appropriate, such criticism may be offered in published papers. However, in no case is personal criticism of the author considered to be appropriate. D. Ethical Obligations of Scientists Publishing outside the Scientiﬁc Literature 1. A scientist publishing in the popular literature has the same basic obligation to be accurate in reporting observations and unbiased in interpreting them as when publishing in a scientiﬁc journal. 2. Inasmuch as laymen may not understand scientiﬁc terminology, the scientist may ﬁnd it necessary to use common words of lesser precision to increase public comprehension. In view of the importance of scientists’ communicating with the general public, some loss of accuracy in that sense can be condoned. The scientist should, however, strive to keep public writing, remarks, and interviews as accurate as possible consistent with effective communication. 3. A scientist should not proclaim a discovery to the public unless the experimental, statistical, or theoretical support for it is of strength sufﬁcient to warrant publication in the scientiﬁc literature. An account of the experimental work and results that support a public pronouncement should be submitted as quickly as possible for publication in a scientiﬁc journal. Scientists should, however, be aware that disclosure of research results in the public press or in an electronic database or bulletin board might be considered by a journal editor as equivalent to a preliminary communication in the scientiﬁc literature. ➤➤➤➤➤ CHAPTER 2 Scientiﬁc Papers T he chemistry community, like other scientiﬁc communities, depends on the communication of scientiﬁc results. Scientists communicate in a variety of ways, but much of the communication is through publication in books and journals. In this chapter, the different types of book and journal presentations are described, along with the components of the standard format for reporting original research. Types of Books Books for the professional scientiﬁc community fall into one of three categories: proceedings volumes, monographs, and handbooks. Proceedings Volumes Books based on meetings are called proceedings volumes. These are multiauthored volumes. The chapters in proceedings volumes may be accounts of original research or literature reviews. Generally, the chapters are developed and expanded from presentations given at symposia, but additional chapters may be written especially for the book to make sure that the coverage of the topic is complete. Proceedings volumes should contain at least one chapter that reviews the subject and also provides an overview of the book to unify the chapters into a coherent treatment of the subject. In a longer book that is divided into sections, each section may need a short overview chapter. Copyright 2006 American Chemical Society 17 18 ➤ The ACS Style Guide Monographs Monographs are books that examine a single topic in detail. They are written by one author or collaboratively by more than one author. Each chapter treats one subdivision of the broader topic. Handbooks Handbooks are large, multiauthored volumes that discuss a ﬁeld in depth. Generally, the individual submissions are short, about three or four pages. Each submission is written by one or two authors and provides a detailed discussion of a narrow topic within the scope of the book. Journal Presentations There are four general types of presentations published in journals: articles, notes, communications, and reviews. Articles Articles, also called full papers, are deﬁnitive accounts of signiﬁcant, original studies. They present important new data or provide a fresh approach to an established subject. The organization and length of an article should be determined by the amount of new information to be presented and by space restrictions within the publication. Notes Notes are concise accounts of original research of a limited scope. They may also be preliminary reports of special signiﬁcance. The material reported must be deﬁnitive and may not be published again later. Appropriate subjects for notes include improved procedures of wide applicability or interest, accounts of novel observations or of compounds of special interest, and development of new techniques. Notes are subject to the same editorial appraisal as full-length articles. Communications Communications, called “letters” or “correspondence” in some publications, are usually preliminary reports of special signiﬁcance and urgency that are given expedited publication. They are accepted if the editor believes that their rapid publication will be a service to the scientiﬁc community. Communications are generally subject to strict length limitations; they must contain speciﬁc results to support their conclusions, but they may not contain nonessential experimental details. Chapter 2: Scientiﬁc Papers ➤ 19 The same rigorous standards of acceptance that apply to full-length articles also apply to communications. Like all types of presentations in journals, communications are submitted to review. In many cases, authors are expected to publish complete details (not necessarily in the same journal) after their communications have been published. Acceptance of a communication, however, does not guarantee acceptance of the detailed manuscript. Reviews Reviews integrate, correlate, and evaluate results from published literature on a particular subject. They seldom report new experimental ﬁndings. Effective review articles have a well-deﬁned theme, are usually critical, and may present novel theoretical interpretations. Ordinarily, reviews do not give experimental details, but in special cases (as when a technique is of central interest), experimental procedures may be included. An important function of reviews is to serve as a guide to the original literature; for this reason, accuracy and completeness of references cited are essential. Standard Format for Reporting Original Research The main text of scientiﬁc papers presenting original research is generally organized into a standard format: abstract, introduction, experimental details or theoretical basis, results, discussion, and conclusions, although not necessarily in this order. This format has become standard because it is suitable for most reports of original research, it is basically logical, and it is easy to use. The reason it accommodates most reports of original research is that it parallels the scientiﬁc method of deductive reasoning: deﬁne the problem, create a hypothesis, devise an experiment to test the hypothesis, conduct the experiment, and draw conclusions. Furthermore, this format enables the reader to understand quickly what is being presented and to ﬁnd speciﬁc information easily. This ability is crucial now more than ever because scientists, if not all professionals, must read much more material than in the past. ✐ Reminder: Journal articles and proceedings chapters are usually orga- nized with an abstract, introduction, experimental details or theoretical basis, results, discussion, and conclusions. Use the standard form for reports of original research whether the report is published in a journal or proceedings volume. Even if the information is more suited to one of the shorter types of presentations, the logic of the standard format applies, although some headings or sections may be omitted or other sections and subsections added. Manuscripts for monographs, handbooks, 20 ➤ The ACS Style Guide literature reviews, or theoretical papers generally do not follow the standard form. Consult author guidelines for information on how to organize these types of presentations or look at previously published work. Regardless of the type of presentation, be sure to present all parts of the paper as concisely as possible. An extremely important step is to check the speciﬁc requirements of the publication targeted and follow them. Some publishers provide templates that help authors produce manuscripts in the requested format. Templates are also useful in making sure that the manuscript is not too long. Most editors require revisions of manuscripts that are not in their requested format. Thus, not following a publication’s requirements can delay publication and make more work for authors. Title The best time to determine the title is after the text is written, so that the title will reﬂect the paper’s content and emphasis accurately and clearly. The title must be brief and grammatically correct but accurate and complete enough to stand alone. A two- or three-word title may be too vague, but a 14- or 15-word title is unnecessarily long. If the title is too long, consider breaking it into title and subtitle. The title serves two main purposes: to attract the potential audience and to aid retrieval and indexing. Therefore, include several keywords. The title should provide the maximum information for a computerized title search. ➤ Choose terms that are as speciﬁc as the text permits, e.g., “a vanadium–iron alloy” rather than “a magnetic alloy”. Avoid phrases such as “on the”, “a study of ”, “research on”, “report on”, “regarding”, and “use of ”. In most cases, omit “the” at the beginning of the title. Avoid nonquantitative, meaningless words such as “rapid” and “new”. ➤ Spell out all terms in the title, and avoid jargon, symbols, formulas, and abbre- viations. Whenever possible, use words rather than expressions containing superscripts, subscripts, or other special notations. Do not cite company names, speciﬁc trademarks, or brand names of chemicals, drugs, materials, or instruments. ➤ Series titles are of little value. Some publications do not permit them at all. If consecutive papers in a series are published simultaneously, a series title may be relevant, but in a long series, paper 42 probably bears so limited a relationship to paper 1 that they do not warrant a common title. In addition, an editor or reviewer seeing the same title repeatedly may reject it on the grounds that it is only one more publication on a general topic that has already been discussed at length. Chapter 2: Scientiﬁc Papers ➤ 21 Byline and Afﬁliation Include in the byline all those, and only those, who made substantial contributions to the work, even if the paper was actually written by only one person. Chapter 1 and Appendix 1-1 in this book are more explicit on this topic. ➤ Many ACS publications speciﬁcally request at least one full given name for each author, rather than only initials. Use your ﬁrst name, initial, and surname (e.g., John R. Smith) or your ﬁrst initial, second name, and surname (e.g., J. Robert Smith). Whatever byline is used, be consistent. Papers by John R. Smith, Jr., J. Smith, J. R. Smith, Jack Smith, and J. R. Smith, Jr., will not be indexed in the same manner; the bibliographic citations may be listed in ﬁve different locations, and ascribing the work to a single author will therefore be difﬁcult if not impossible. ➤ Do not include professional, religious, or ofﬁcial titles or academic degrees. ➤ The afﬁliation is the institution (or institutions) at which the work was conducted. If the author has moved to another institution since the work was done, many publications include a footnote giving the current address. Contact the editor about this. ➤ If there is more than one author, use an asterisk or superscript (check the speciﬁc publication’s style) to indicate the author or authors to whom correspondence should be addressed. Clarify all corresponding authors’ addresses by accompanying footnotes if they are not apparent from the afﬁliation line. E-mail addresses may be included in corresponding author footnotes. Abstract Most publications require an informative abstract for every paper, even if they do not publish abstracts. For a research paper, brieﬂy state the problem or the purpose of the research, indicate the theoretical or experimental plan used, summarize the principal ﬁndings, and point out major conclusions. Include chemical safety information when applicable. Do not supplement or evaluate the conclusions in the abstract. For a review paper, the abstract describes the topic, scope, sources reviewed, and conclusions. Write the abstract last to be sure that it accurately reﬂects the content of the paper. ✐ Reminder: The abstract allows the reader to determine the nature and scope of the paper and helps technical editors identify key features for indexing and retrieval. ➤ Although an abstract is not a substitute for the article itself, it must be concise, self-contained, and complete enough to appear separately in abstract publications. Often, authors’ abstracts are used with little change in abstract pub- 22 ➤ The ACS Style Guide lications. The optimal length is one paragraph, but it could be as short as two sentences. The length of the abstract depends on the subject matter and the length of the paper. Between 80 and 200 words is usually adequate. ➤ Do not cite references, tables, ﬁgures, or sections of the paper in the abstract. Do not include equations, schemes, or structures that require display on a line separate from the text. ➤ Use abbreviations and acronyms only when it is necessary to prevent awk- ward construction or needless repetition. Deﬁne abbreviations at ﬁrst use in the abstract (and again at ﬁrst use in the text). Introduction A good introduction is a clear statement of the problem or project and the reasons for studying it. This information should be contained in the ﬁrst few sentences. Give a concise and appropriate background discussion of the problem and the signiﬁcance, scope, and limits of the work. Outline what has been done before by citing truly pertinent literature, but do not include a general survey of semirelevant literature. State how your work differs from or is related to work previously published. Demonstrate the continuity from the previous work to yours. The introduction can be one or two paragraphs long. Often, the heading “Introduction” is not used because it is superﬂuous; opening paragraphs are usually introductory. Experimental Details or Theoretical Basis In research reports, this section can also be called “Experimental Methods”, “Experimental Section”, or “Materials and Methods”. Be sure to check the speciﬁc publication for the correct title of this section. For experimental work, give sufﬁcient detail about the materials and methods so that other experienced workers can repeat the work and obtain comparable results. When using a standard method, cite the appropriate literature and give only the details needed. ➤ Identify the materials used and give information on the degree of and criteria for purity, but do not reference standard laboratory reagents. Give the chemical names of all compounds and the chemical formulas of compounds that are new or uncommon. Use meaningful nomenclature; that is, use standard systematic nomenclature where speciﬁcity and complexity require, or use trivial nomenclature where it will adequately and unambiguously deﬁne a well-established compound. ➤ Describe apparatus only if it is not standard or not commercially available. Giving a company name and model number in parentheses is nondistracting and adequate to identify standard equipment. Chapter 2: Scientiﬁc Papers ➤ 23 ➤ Avoid using trademarks and brand names of equipment and reagents. Use generic names; include the trademark in parentheses after the generic name only if the material or product used is somehow different from others. Remember that trademarks often are recognized and available as such only in the country of origin. In ACS publications, do not use trademark (™) and registered trademark (®) symbols. ➤ Describe the procedures used, unless they are established and standard. ➤ Note and emphasize any hazards, such as explosive or pyrophoric tendencies and toxicity, in a separate paragraph introduced by the heading “Caution:”. Include precautionary handling procedures, special waste disposal procedures, and any other safety considerations in adequate detail so that workers repeating the experiments can take appropriate safety measures. Some ACS journals also indicate hazards as footnotes on their contents pages. In theoretical reports, this section is called, for example, “Theoretical Basis” or “Theoretical Calculations” instead of “Experimental Details” and includes sufﬁcient mathematical detail to enable other researchers to reproduce derivations and verify numerical results. Include all background data, equations, and formulas necessary to the arguments, but lengthy derivations are best presented as supporting information. Results Summarize the data collected and their statistical treatment. Include only relevant data, but give sufﬁcient detail to justify the conclusions. Use equations, ﬁgures, and tables only where necessary for clarity and brevity. Extensive but relevant data should be included in supporting information. Discussion The purpose of the discussion is to interpret and compare the results. Be objective; point out the features and limitations of the work. Relate your results to current knowledge in the ﬁeld and to the original purpose in undertaking the project: Was the problem resolved? What has been contributed? Brieﬂy state the logical implications of the results. Suggest further study or applications if warranted. Present the results and discussion either as two separate sections or as one combined section if it is more logical to do so. Do not repeat information given elsewhere in the manuscript. Conclusions The purpose of the conclusions section is to put the interpretation into the context of the original problem. Do not repeat discussion points or include irrelevant material. Conclusions should be based on the evidence presented. 24 ➤ The ACS Style Guide Summary A summary is unnecessary in most papers. In long papers, a summary of the main points can be helpful, but be sure to stick to the main points. If the summary itself is too long, its purpose is defeated. Acknowledgments Generally, the last paragraph of the paper is the place to acknowledge people, organizations, and ﬁnancing. As simply as possible, thank those persons, other than coauthors, who added substantially to the work, provided advice or technical assistance, or aided materially by providing equipment or supplies. Do not include their titles. If applicable, state grant numbers and sponsors here, as well as auspices under which the work was done, including permission to publish if appropriate. Follow the publication’s guidelines on what to include in the acknowledgments section. Some journals permit ﬁnancial aid to be mentioned in acknowledgments, but not meeting references. Some journals put ﬁnancial aid and meeting references together, but not in the acknowledgments section. References In many books and journals, references are placed at the end of the article or chapter; in others, they are treated as footnotes. In any case, place the list of references at the end of the manuscript. In ACS books and most journals, the style and content of references are standard regardless of where they are located. Follow the reference style presented in Chapter 14. The accuracy of the references is the author’s responsibility. Errors in references are one of the most common errors found in scientiﬁc publications and are a source of frustration to readers. Increasingly, hypertext links are automatically generated in Web-based publications, but this cannot be done for references containing errors. If citations are copied from another source, check the original reference for accuracy and appropriate content. ✐ Reminder: The accuracy of the references is the author’s responsibility. Special Sections This discussion on format applies to most manuscripts, but it is not a set of rigid rules and headings. If the paper is well organized, scientiﬁcally sound, and appropriate to the publication, adding other sections and subsections may be helpful to readers. For example, an appendix contains material that Chapter 2: Scientiﬁc Papers ➤ 25 is not critical to understanding the text but provides important background information. Supporting Information Material that may be essential to the specialized reader but not require elaboration in the paper itself is published as supporting information, usually on the journal’s Web page. Examples of supporting information include large tables, extensive ﬁgures, lengthy experimental procedures, mathematical derivations, analytical and spectral characterization data, biological test data for a series, molecular modeling coordinates, modeling programs, crystallographic information ﬁles, instrument and circuit diagrams, and expanded discussions of peripheral ﬁndings. More journals are encouraging this type of publishing to keep printed papers shorter. For ACS journals, supporting information is available immediately by linking to it from the citing paper on the Web. For example, for the article “Vanadium-Based, Extended Catalytic Lifetime Catechol Dioxygenases: Evidence for a Common Catalyst” by Cindy-Xing Yin and Richard G. Finke in The Journal of the American Chemical Society 2005, 127, 9003–9013, the supporting information consists of two ﬁles, ja051594esi20050517_053152.pdf (453 K) and ja051594erom20050320_064528.cif (24 K). When including supporting information, place a statement to that effect at the end of the paper, using the format speciﬁed in the author instructions for the speciﬁc journal. For complete instructions on how to prepare this material for publication, check the author instructions for the publication. Web-Enhanced Objects Some publishers, including ACS, have started exploring various Web-based technologies to enhance the way that information in a research article is conveyed. Selected papers in Web editions may contain Web-enhanced objects (WEOs) to supplement a reader’s understanding of the research being reported. These types of ﬁles include color ﬁgures (including three-dimensional, rotatable ﬁgures), chemical structures, animations, spectra, video, and sound ﬁles. Links to WEOs will appear in the Web edition of the paper. These objects, although not essential to the understanding of the science, should help to augment a reader’s understanding of the research being reported. The types of objects suitable for this form of publication should be viewable with commonly available plugins (e.g., Chime) or helper applications (e.g., WebLab Viewer, RasMol), which allow viewing and manipulating these objects within the HTML ﬁle itself or in a separate window. For example, a ﬁgure in the journal article “Orientation and Phase Transitions of Fat Crystals under Shear” by Gianfranco Mazzanti, Sarah E. Guthrie, Eric B. Sirota, Alejandro G. Marangoni, and Stefan H. J. Idziak, in 26 ➤ The ACS Style Guide Crystal Growth & Design 2003, 3, 721–725, is supplemented by a movie WEO (in .mov format) depicting the time sequence of synchrotron X-ray diffraction patterns for the crystallization of cocoa butter in chocolate (see http://pubs.acs.org/ isubscribe/journals/cgdefu/asap/objects/cg034048a/Mazzantivideouip.mov). As with other types of special information, authors should check the author guidelines for the publication for instructions on how to prepare and submit WEOs. ➤➤➤➤➤ CHAPTER 3 The Editorial Process P ublishing a manuscript, whether intended for a journal or a book, is a process. It has four stages: the draft manuscript, manuscript review, the ﬁnal manuscript, and processing of accepted manuscripts. Along the way, responsibility for the different stages passes from the author, to the journal or book editor, back to the author, and ﬁnally to the technical editor. This chapter provides an overview of each of these stages as they evolve in scientiﬁc, technical, and medical (STM) publishing. The Draft Manuscript Getting Started Before beginning to write, authors should review the ethical principles of scientiﬁc publication (see Chapter 1). The editorial process is supported by the ethical obligations of authors, editors, reviewers, and readers. Author integrity and adherence to the principles that guide scientiﬁc publications—such as deciding when it is the appropriate time to publish, determining who should author the manuscript, and providing the proper attribution and context for the research— are as integral to the success of scientiﬁc publication as providing science that is sound and of high quality. Although there is no ﬁxed set of “writing rules” to be followed like a cookbook recipe or an experimental procedure, some guidelines can be helpful. Start by considering the questions in Box 3-1; answering these questions will clarify your goals and make it easier to write the manuscript with the proper amount of detail. It will also make it easier for the book or journal editor to determine the Copyright 2006 American Chemical Society 27 28 ➤ The ACS Style Guide ➤➤➤➤➤ Box 3-1. Questions for Drafting Your Manuscript What is the function or purpose of this manuscript? Are you describing original and signiﬁcant research results? Are you reviewing the literature? Are you providing an overview of the topic? Something else? Who is the audience? Why would they want to read your manuscript? What will you need to tell them to help them understand your work? How is your work different from that described in other reports on the same subject? (Unless you are writing a review, be sure that your manuscript will make an original contribution. Most STM publishers, including ACS, do not publish previously published material.) What is the best format for publishing this manuscript—as a journal article, book, or book chapter? If you choose a journal article, which journal is most appropriate? (Links to ACS journals can be found at http://pubs.acs.org/about.html.) manuscript’s suitability for the publication. Writing is like so many other things: once the goal is identiﬁed, the details fall into place. After you have determined the function of the manuscript and identiﬁed the audience, review your material for completeness or excess. Reports of original research, whether intended for a journal or a book, can be organized in the standard format: abstract, introduction, experimental details or theoretical basis, results, discussion, and conclusions. These sections are discussed in Chapter 2. Keep in mind that scientiﬁc writing is not literary writing. Scientiﬁc writing serves a purpose completely different from that of literary writing, and it must therefore be precise and unambiguous. You and your colleagues probably have been discussing the project for months, so the words seem familiar, common, and clear to you. However, the readers will not have been part of these discussions. Many words are clear when speaking because you can amplify the meaning with gestures, expressions, and vocal inﬂections—but when these same words are written, they may be clear only to you. Chapter 4 presents strategies on how to write clearly and concisely as well as to select words that convey the meaning intended. If English is not your ﬁrst language, ask an English-speaking colleague—if possible, a native English speaker—for help with grammar and diction. Publishers’ Requirements An extremely important step is to check the speciﬁc requirements of the publication and to follow them. Journals often specify a format, the number of pages, Chapter 3: The Editorial Process ➤ 29 what software packages or ﬁle formats are acceptable, how to cite references, and many other aspects of manuscript preparation. Requirements can vary from journal to journal even if the same publisher publishes them. Author guidelines for journals are generally posted on the Web at the journal’s Web site, and they are also typically published in the ﬁrst issue of each year. Book publishers also have author guidelines that need to be followed to expedite publication. Understanding the requirements for the manuscript cannot be overemphasized. Publishing with ACS: The author guidelines for ACS journals can be seen at http://paragon.acs.org/paragon/index.jsp (see “Author Information”). The author guidelines for ACS books can be found at http://pubs. acs.org/books (see “Info for Authors”). Some publishers provide templates for authors to use when preparing their manuscripts. Use of a template makes it easier for authors to control margins, fonts, and paragraph styles, as well as the length of the manuscript. It also facilitates peer review by placing tabular and graphical material near the discussion in the text and providing journal and book editors with a single ﬁle to work with. Templates are generally available for Windows and Macintosh platforms, and they can be downloaded from a publisher’s or journal’s Web page. Publishing with ACS: For ACS journals, templates can be accessed at http://paragon.acs.org/paragon/index.jsp (see “Download Manuscript Templates”). For ACS proceedings books, templates are available at http://pubs.acs.org/books/authorinfo.shtml (see “Request instructions on how to prepare your camera-ready manuscript”). Artwork As you write your draft manuscript, consider where structures, schemes, ﬁgures, and tables could be used appropriately to illustrate or support the material. Wellplaced and well-designed artwork communicates information effectively, but too much artwork can be distracting. Few scientists have access to graphic arts professionals. Consequently, chemical professionals need to know how to prepare art for manuscripts. Fortunately, software packages are available that can be easily mastered to produce goodlooking graphs, charts, schemes, and structures. Chapters 15, 16, and 17 provide guidelines on when to use artwork and how to create ﬁgures, tables, or chemical structures and schemes that publishers can use effortlessly. These chapters also describe how to number ﬁgures, tables, structures, and schemes. Sometimes you may wish to use artwork that has been previously published, whether from your own publications or from those of other authors. To use pre- 30 ➤ The ACS Style Guide viously published artwork, you must get permission from the copyright holder, which is generally the publisher, even if you wrote the manuscript. Because it can take some time to secure reprint permission, it is a good idea to start obtaining permissions as you prepare your draft manuscript. If you wait until your manuscript is accepted for publication to initiate any permissions correspondence, publication of your manuscript may be delayed because publishers generally will not begin working on a manuscript when permissions are missing. Chapter 7 discusses how to get permission to reprint ﬁgures that have been previously published. Publishers’ policies, and forms if required, are generally posted on their Web sites. Publishing with ACS: Authors can reprint artwork previously published in ACS books and journals in other ACS publications without permission, provided that ACS is the original copyright holder. ACS’s copyright policy and procedures can be found at http://pubs.acs.org/copyright_info.html. Journals vary in their requirements about where tables and ﬁgures are placed in the manuscript. Some journals permit tables and ﬁgures to be inserted into the text for the draft but require that the tables and ﬁgures be submitted separately in the ﬁnal manuscript. Other journals request that the tables and ﬁgures be embedded in the text. Some publishers accept ﬁgures prepared in a wide range of software packages, whereas others specify use of certain drawing programs. Check the speciﬁc requirements of the publication targeted before submitting the draft manuscript. Publishing with ACS: Placement of artwork submitted to ACS journals depends on whether the manuscript is submitted through Paragon or the Paragon Plus environment. Be sure to check the author guidelines for the speciﬁc journal. References References are an important component of every scholarly manuscript. Having complete and accurate references is the author’s responsibility. Errors in references are one of the most common mistakes authors make. Although correct citations have always been important, the increasing number of hypertext links in Web-based publications makes correct citations more important than ever. Given the volume of manuscripts that publishers produce yearly, technical editors cannot verify each reference in each manuscript. The citation of references in text is a subject that varies widely from journal to journal and publisher to publisher. There are three ways to cite references in text in ACS publications: superscript numbers, italic numbers in parentheses, or author name and year of publication. Authors are encouraged to check the Chapter 3: The Editorial Process ➤ 31 author guidelines for a speciﬁc publication to ﬁnd information on citing references. Chapter 14 explains how to cite references in ACS publications and how to format references from a variety of publications, in both print and electronic formats. ✐ Reminder: Although correct citations have always been important, the increasing number of hypertext links in Web-based publications makes correct citations more important than ever. Revising the Draft Manuscript Once you have written your initial draft, the next step is a careful revision with an eye to organization, content, and editorial style, beginning with the questions in Box 3-2. Several chapters in this book are designed to help you communicate clearly. Chapter 9 reviews grammar, punctuation, and spelling. Chapter 10 provides guidelines on stylistic and editorial conventions, such as hyphenation and capitalization. Chapter 10 also includes a large appendix with abbreviations, acronyms, and symbols. Guidelines for using numbers, mathematics, and units of measure are given in Chapter 11. Two other chapters focus on more speciﬁc issues related to chemistry. Chapter 12 examines the use of proper chemical nomenclature. It provides rules for general chemistry nomenclature, as well as nomenclature in several specialized areas, such as polymer chemistry, biological chemistry, and combinatorial chemistry. Chapter 13 presents a quick reference guide for the use of typefaces, Greek letters, superscripts and subscripts, and special symbols that are commonly used in chemistry. Chapter 13 also includes an appendix containing symbols for commonly used physical quantities. Manuscript Review When your draft manuscript is complete, check the journal or book author guidelines again for information on how and where to submit your draft. Some editors request that authors suggest possible reviewers. Some journals require that multiple copies of a draft manuscript be submitted and only accept manuscripts through the mail. Other journals request that the manuscript be submitted electronically via e-mail. Still others, like ACS, are using a Web-based system where authors submit a word-processing ﬁle or a PDF. For more information on submitting manuscripts using a Web-based system, see Chapter 5. Once the editor has reviewed the manuscript and determined that it is appropriate for the publication, the peer-review process begins. Chapter 6 describes peer review and the responsibilities of reviewers and authors. 32 ➤ The ACS Style Guide ➤➤➤➤➤ Box 3-2. Questions for Revising Your Manuscript Does your manuscript as it is written perform the function—new research, literature review, or topic overview—that you identiﬁed before you began your draft? Do you still think the format you selected—journal article, book, book chapter—is the best choice? Have you explained terms, concepts, and procedures in a way that is appropriate to the audience you identiﬁed at the start? Is your material presented in a logical fashion, so that a reader can easily follow your reasoning? Is the manuscript too long? If so, what sections could be eliminated or possibly used as supporting information? Do some sections need to be expanded to further clarify the material? Are the sentences clear and unambiguous? Are all the words spelled correctly and technical terms used appropriately? Did you follow generally accepted conventions—such as those in this book—for communicating math and chemistry? Could you use another opinion? You may ﬁnd it helpful to ask a colleague, preferably one who is not closely involved with the research on which the manuscript is based, and preferably a native English speaker, to read and comment on your draft. The Final Manuscript If your manuscript is accepted, the editor of the book or journal will return the peer-reviewed manuscript with a cover letter synthesizing the reviewers’ comments and indicating what changes must be made for the ﬁnal manuscript to be accepted. You, the author, then revise the manuscript accordingly. When you submit your ﬁnal manuscript, include a cover letter indicating what changes you made. If you decide not to make some of the requested changes, you should write a rebuttal and send it with your ﬁnal manuscript. For more information, see Chapter 6. Authors are encouraged to submit all the paperwork with the ﬁnal, revised manuscript. This includes all necessary permissions correspondence and, if required, a signed form transferring copyright from the author to the publisher. Chapter 7 gives a general introduction to copyright. If the manuscript is transmitted electronically, mail the forms separately. Chapter 3: The Editorial Process ➤ 33 ✐ Reminder: When you submit your ﬁnal manuscript, you should include the ﬁnal versions of text, tables, and illustrations, as well as any necessary permissions correspondence and a signed copyright transfer form. Finally, keep a copy of the revised manuscript and all permissions correspondence. You will need the revised manuscript to check against the proofs that your publisher sends. Copies of the permissions correspondence can save you time and effort if the permissions correspondence gets lost or separated from your manuscript. Processing of Accepted Manuscripts Journal editors and multiauthored book editors send accepted manuscripts directly to the publisher. Authors of monographs interact directly with the publisher, generally through an acquisitions editor. Accepted manuscripts go through three phases before publication: technical editing, prooﬁng and review by the author, and correction by the publisher. Technical Editing During the process of creating a book or journal issue, authors’ electronic wordprocessing ﬁles are manipulated in a variety of ways. Files are tagged to identify data elements for print production and links for online products. Artwork is prepared for both publication media. The manuscript is copyedited to ensure consistency, clarity, and grammatical accuracy; changes are introduced to ensure the use of standard chemical conventions, graphics presentation, and tabular format. Copy editors often contact authors or query them at the proof stage for clariﬁcation of material. Author’s Proof One author, generally the author to whom correspondence should be addressed, receives a proof of the manuscript for ﬁnal approval before publication. Papers are not generally released for printing until the author’s proof or other approval has been received. Hence, proofs should be checked and returned promptly according to individual journal or book instructions. Publishing with ACS: ACS journals request that proofs be returned within 48 hours of receipt. Authors should check proofs very carefully and submit all of the corrections at one time; see Box 3-3 and Appendix 3-1 for information about reviewing 34 ➤ The ACS Style Guide ➤➤➤➤➤ Box 3-3. Tips for Checking Proofs ➤ If you are instructed to return changes via the Web, list all corrections, revisions, and additions and clearly identify their location. ➤ If you are instructed to return changes in hard copy (paper printouts), mark corrections legibly in the margins of the proofs as instructed by the publisher. Do not erase or obliterate type; instead, strike one line through copy to be deleted and write the change in the margin. ➤ Clarify complicated corrections by rewriting the entire phrase or sentence. ➤ Check all text, data, and references against the original manuscript. Pay particular attention to equations; formulas; tables; captions; spelling of proper names; and numbering of equations, illustrations, tables and references. ➤ Answer explicitly all queries made by the technical editor. Proofreader’s marks and a sample of marked manuscript are given in Appendix 3-1. proofs. Only corrections and necessary changes can be made to proofs. Although all authors may look at the proofs, only the corresponding author should submit corrections. Extensive changes may require editorial approval, which delays publication. Printer’s errors are corrected at no cost to authors, but some publishers charge authors the cost of extensive production work made necessary by their own alterations. Publication After you return your corrected proofs, the technical editor will review them and ensure that the corrections are made properly. ASAP (As Soon As Publishable) Articles Many STM publishers, including ACS, publish journal articles on the Web before publishing them in print. Papers accepted for publication in ACS journals will be posted on the “Articles ASAP” page on the journal Web site as soon as they are ready for publication; that is, when the proofs are corrected and all author concerns are resolved. Publication on the Web usually occurs within four working days of receipt of proof corrections; this can be any time from three to six weeks before the date of the printed issue. Once a paper appears on the Web, ACS and the scientiﬁc community consider it published. Chapter 3: The Editorial Process ➤ 35 Article Reprints and Complimentary Copies Generally, authors receive a form for reprint orders with the author proof. Authors should follow the instructions on the form. Some publishers provide electronic reprints, as well as paper reprints. Customarily, there is a charge for paper reprints, and reprints with color artwork cost more. Book authors sometimes also receive complimentary copies of the volume in which their chapter appears. On contributions with more than one author, the number of complimentary copies is generally limited; that is, not all authors will receive complimentary copies. Corrections to Published Manuscripts Corrections of consequence to a paper that has already been published should be sent to the editor. Most journals publish corrections soon after they have been received. Some journals have a speciﬁc format for additions or corrections; check the author guidelines. In books, errata sheets will be printed and included in every book, and the book itself will be corrected before reprinting. However, additions and corrections generally reﬂect poorly on the authors, and careful manuscript preparation and attention to detail in the entire publication process can prevent the necessity for subsequent corrections. ➤➤➤➤➤ APPENDIX 3-1 Proofreaders’ Marks Publishers long ago established conventions for marking changes to manuscripts and proofs. These conventions, known as proofreaders’ marks, evolved as an economical and precise shorthand for indicating on paper various types of changes. Changes to double-spaced manuscript are marked one way (Figure 3A-1). Authors may be called on to interpret these proofreaders’ marks if the publisher has copyediting done by hand, on paper. Common proofreaders’ marks for manuscripts are presented in Figure 3A-2. Note that corrections to manuscripts are made in place (not in the margins) and usually need no additional explanation. Changes to typeset proofs are marked somewhat differently (Figure 3A-3). Authors may be called on to use this proofreading method if the publisher supplies hard-copy (paper) proofs. Common proofreaders’ marks for proofs (also called galleys or page proofs) are presented in Figure 3A-4. Note that corrections to proofs are made in two places: a minimal mark is made in the typeset text, to indicate where a change is being made, and an explanatory mark is made in the margin to describe the exact change. For example, a carat mark (^) in the typeset text indicates where new words are to be inserted; the words themselves are written in the margin. If there is more than one change to a typeset line, the changes in the margin are separated by slashes. (If you want to insert a slash, you should write out the word “slash” and circle it in the margin.) Two slashes in a row indicate that the ﬁrst correction should be repeated. Try not to black out or obliterate the typeset characters. Avoid using arrows and lines to indicate where corrections go because more than one or two on a page breed confusion. 36 Chapter 3: The Editorial Process Figure 3A-1. Sample of a manuscript copyedited by hand. ➤ 37 38 ➤ The ACS Style Guide Strike through to delete a word or words. Triple underline to capitalize the “w”. Slash to make the “w” lowercase. Transpose two letters. Transpose two words. Double underline to make “ord” small capitals Draw a wavy line to indicate bold face. Underline to indicate italic type. Draw an inverted carat to indicate superscript. Draw a carat to indicate subscript. Put dots or short dashes under copy that you wish to retain as it originally appeared. Figure 3A-2. Common proofreaders’ marks for copyediting manuscripts. Figure 3A-3. Sample of a marked proof. Chapter 3: The Editorial Process ➤ 39 Operational Signs Typographical Signs Delete Lowercase a capital letter Close up; delete space Capitalize a lowercase letter Delete and close up Set in small capitals Insert space Set in italic type Begin new paragraph Set in roman type Run paragraphs together Set in boldface type One em space Wrong font; set in correct type Move right Superscript Move left Subscript Center Punctuation Marks Move up Insert comma Move down Insert apostrophe (or single quotation mark) Align horizontally Insert quotation marks Align vertically Insert period Transpose Insert question mark Spell out Insert semicolon Let it stand Insert colon Flush left Insert hyphen Flush right Insert em dash Center Insert en dash Figure 3A-4. Common proofreaders’ marks for marking proofs. ➤➤➤➤➤ CHAPTER 4 Writing Style and Word Usage E very writer has a personal style, but all good writing tends to observe guidelines and conventions that communicate meaning clearly and exactly to readers. Scientiﬁc writing, in particular, must be precise and unambiguous to be effective. This chapter presents guidelines for correct sentence structure and word usage. Other chapters of this book present topics also related to good writing style. Chapter 2 discusses the parts of a scientiﬁc paper; Chapter 3 presents an overview of the editorial process. Chapters in Part 2 address more specialized rules for usage; see, especially, Chapter 9 on grammar, punctuation, and spelling and Chapter 10 on editorial style. Correct Sentence Structure Good organization (see Chapter 2) and sentence structure are an author’s primary tools for conveying information in a logical, persuasive manner. When the words in a sentence are placed so that the reader follows easily from one fact or point to the next, then the reader is best able to comprehend the author’s intended meaning. Poorly structured or ordered sentences create confusion for readers, who are then unable to understand accurately the author’s meaning. Short, simple declarative sentences—that is, sentences that make statements, rather than pose questions, issue commands, or exclaim—are the easiest to write and the easiest to read. They are also usually clear. However, too many short sentences in a row can sound abrupt or monotonous. They also can place too heavy a burden on the reader to connect the ideas from one sentence to the next. To Copyright 2006 American Chemical Society 41 42 ➤ The ACS Style Guide add sentence variety and to enhance the ﬂow of ideas, it is better to start with simple declarative sentences and then combine some of them, rather than to start with long rambling sentences and then try to shorten them. Two or more simple sentences (sentences with one independent clause and no subordinate clauses) can be combined to form a compound sentence. A complex sentence is created by adding one or more subordinate clauses to a simple sentence. A clause is a group of words that has a subject and a verb. If a clause can stand all by itself, it is an independent clause. If a clause cannot stand alone, it is a dependent or subordinate clause. Verbs Voice A sentence is said to be in active voice when the subject of the sentence is the doer of the action indicated by the verb. The subject of an active verb is doing the action of the verb. In passive voice, the subject is the receiver of the action indicated by the verb. ➤ Use the active voice when it is less wordy and more direct than the passive. poor The fact that such processes are under strict stereoelectronic control is demonstrated by our work in this area. better Our work in this area demonstrates that such processes are under strict stereoelectronic control. ➤ Use the passive voice when the doer of the action is unknown or not important or when you would prefer not to specify the doer of the action. The solution is shaken until the precipitate forms. Melting points and boiling points have been approximated. Identity speciﬁcations and tests are not included in the monographs for reagent chemicals. Tense Using the appropriate verb tense helps to orient the reader as to the nature of the information. ➤ Simple past tense is correct for stating what was done, either by others or by you. The solutions were heated to boiling. Chapter 4: Writing Style and Word Usage ➤ 43 Jones reviewed the literature and gathered much of this information. We found that relativistic effects enhance the bond strength. The structures were determined by neutron diffraction methods. ➤ Present tense is correct for statements of fact. Absolute rate constants for a wide variety of reactions are available. Hyperbranched compounds are macromolecular compounds that contain a branching point in each structural repeat unit. ➤ Present and simple past tenses may both be correct for results, discussion, and conclusions. The characteristics of the voltammetric wave indicate that electron transfer occurs spontaneously. The absence of substitution was conﬁrmed by preparative-scale electrolysis. IR spectroscopy shows that nitrates are adsorbed and are not removed by washing with distilled water. However, the use of present or simple past tense for results, discussion, and conclusions should be consistent within a paper. Other Forms ➤ It is acceptable to use split inﬁnitives to avoid awkwardness or ambiguity. awkward The program is designed to assist ﬁnancially the student who is considering a career in chemistry. better The program is designed to ﬁnancially assist the student who is considering a career in chemistry. ambiguous The bonded phases allowed us to investigate fully permanent gases. better The bonded phases allowed us to fully investigate permanent gases. Subjects and Subject–Verb Agreement ➤ Use ﬁrst person when it helps to keep your meaning clear and to express a purpose or a decision. Jones reported xyz, but I (or we) found …. 44 ➤ The ACS Style Guide I (or we) present here a detailed study …. My (or our) recent work demonstrated …. To determine the effects of structure on photophysics, I (or we) …. However, avoid clauses such as “we believe”, “we feel”, and “we can see”, as well as personal opinions. ➤ Subjects and verbs must agree in person and number; this important point is discussed in detail in Chapter 9. Sentence Modiﬁers Modiﬁers made up of phrases or dependent clauses can be added to simple sentences to indicate, for example, cause and effect, or time sequence, or comparison. ➤ A restrictive phrase or clause is one that is essential to the meaning of the sen- tence. Restrictive modiﬁers are not set off by commas. Only doctoral students who have completed their coursework may apply for this grant. Several systems that take advantage of this catalysis can be used to create new palladium compounds. ➤ A nonrestrictive phrase or clause is one that adds meaning to the sentence but is not essential; in other words, the meaning of the basic sentence would be the same without it. Nonrestrictive modiﬁers are set off by commas. Doctoral students, who often have completed their coursework, apply for this teaching fellowship. Several systems, which will be discussed below, take advantage of this catalytic reaction. ➤ A misplaced modiﬁer is one that is placed next to the wrong word in the sen- tence, so it inadvertently misrepresents the author’s intended meaning. incorrect We commenced a new round of experiments unable to point to meaningful conclusions. correct Unable to point to meaningful conclusions, we commenced a new round of experiments. Chapter 4: Writing Style and Word Usage ➤ 45 ➤ A dangling modiﬁer is one that lacks a word in the sentence to modify in a logical or sensible way. It should not be confused with an absolute construction, which modiﬁes an entire sentence. (See also the discussion of dangling modiﬁers in Chapter 9.) incorrect Adding 2 mL of indicator solution, the end point for the titration was reached. correct Adding 2 mL of indicator solution, we reached the end point for the titration. When we added 2 mL of indicator solution, the end point for the titration was reached. Sentence Construction and Word Order ➤ Use an afﬁrmative sentence rather than a double negative. instead of consider using This reaction is not uncommon. This reaction is common. This reaction is not rare. This reaction occurs about 40% of the time. This transition was not unexpected. This transition was expected. We knew that such transitions were possible. This strategy is not infrequently used. This strategy is frequently used. This strategy is occasionally used. This result is not unlikely to occur. This result is likely to occur. This result is possible. ➤ Watch the placement of the word “only”. It has different meanings in differ- ent places in the sentence. Only the largest group was injected with the test compound. (Meaning: and no other group) The largest group was only injected with the test compound. (Meaning: and not given the compound in any other way) The largest group was injected with only the test compound. (Meaning: and no other compounds) The largest group was injected with the only test compound. (Meaning: there were no other test compounds) ➤ Be sure that the antecedents of pronouns are clear; in other words, when you use a pronoun (for example, “he”, “she”, “it”, or “they”), the noun to which the pronoun refers should be obvious (for example, “Isaac Newton”, “Marie Curie”, 46 ➤ The ACS Style Guide “the compound”, or “the research team”). This is particularly true for the pronouns “this” and “that”. If there is a chance of ambiguity, use a noun to clarify your meaning. ambiguous The photochemistry of transition-metal carbonyl complexes has been the focus of many investigations. This is due to the central role that metal carbonyl complexes play in various reactions. unambiguous The photochemistry of transition-metal carbonyl complexes has been the focus of many investigations. This interest is due to the central role that metal carbonyl complexes play in various reactions. ➤ Use the proper subordinating conjunctions. (Conjunctions join parts of a sen- tence; subordinating conjunctions join subordinate clauses to the main sentence.) “While” and “since” have strong connotations of time. Do not use them where you mean “although”, “because”, or “whereas”. poor Since solvent reorganization is a potential contributor, the selection of data is very important. better Because solvent reorganization is a potential contributor, the selection of data is very important. poor While the reactions of the anion were solvent-dependent, the corresponding reactions of the substituted derivatives were not. better Although the reactions of the anion were solvent-dependent, the corresponding reactions of the substituted derivatives were not. The reactions of the anion were solvent-dependent, but (or whereas) the corresponding reactions of the substituted derivatives were not. Parallelism Parallelism, or parallel construction, is the use of words or groups of words of equal grammatical rank. Equal grammatical rank means that words are connected only to words, phrases only to phrases, subordinate clauses only to other subordinate clauses, and sentences only to other sentences. Establish parallel construction by using coordinating conjunctions, correlative conjunctions, and correlative constructions. Chapter 4: Writing Style and Word Usage ➤ 47 ➤ A coordinating conjunction is a single word, such as “and”, “but”, “or”, “nor”, “yet”, “for”, and sometimes “so”. incorrect Compound 12 was prepared analogously and by Lee’s method (5). correct Compound 12 was prepared in an analogous manner and by Lee’s method (5). ➤ A correlative conjunction is a pairing of words, such as “either … or”; “neither … nor”; “both … and”; “not only … but also”; and “not … but”. incorrect The product was washed either with alcohol or acetone. correct The product was washed with either alcohol or acetone. The product was washed either with alcohol or with acetone. incorrect It is best to use alternative methods both because of the condensation reaction and because the amount of water in the solvent increases with time. correct It is best to use alternative methods both because of the condensation reaction and because of the increase in the amount of water in the solvent with time. incorrect Not only was the NiH functionality active toward the C-donor derivatives but also toward the N donors. correct The NiH functionality was active not only toward the C-donor derivatives but also toward the N donors. The NiH functionality was not only active toward the C-donor derivatives but also active toward the N donors. Not only was the NiH functionality active toward the C-donor derivatives, but it was also active toward the N donors. ➤ A correlative construction is a sentence structure that uses “as … as” (for example, “as well as”). He performed the experiment as well as I could have done it. 48 ➤ The ACS Style Guide ➤ Do not try to use parallel construction around the word “but” when it is not used as a coordinating conjunction. Increasing the number of ﬂuorine atoms on the adjacent boron atom decreases the chemical shift, but only by a small amount. The reaction proceeded readily, but with some decomposition of the product. ➤ Use parallel constructions in series and lists, including section headings and subheadings in text and tables and listings in ﬁgure captions. Comparisons ➤ Introductory phrases that imply comparisons should refer to the subject of the sentence and be followed by a comma. incorrect Unlike alkali-metal or alkaline-earth-metal cations, hydrolysis of trivalent lanthanides proceeds signiﬁcantly at this pH. correct Unlike that of alkali-metal or alkaline-earth-metal cations, hydrolysis of trivalent lanthanides proceeds signiﬁcantly at this pH. Unlike alkali-metal or alkaline-earth-metal cations, trivalent lanthanides hydrolyze signiﬁcantly at this pH. incorrect In contrast to the bromide anion, there is strong distortion of the free ﬂuoride anion on the vibrational spectroscopy time scale. correct In contrast to the bromide anion, the free ﬂuoride anion is strongly distorted on the vibrational spectroscopy time scale. ➤ Use the verb “compare” followed by the preposition “to” when similarities are being noted. Use “compare” followed by the preposition “with” when differences are being noted. Only things of the same class should be compared. Compared to compound 3, compound 4 shows an NMR spectrum with corresponding peaks. Compared with compound 3, compound 4 shows a more complex NMR spectrum. ➤ Do not omit words needed to complete comparisons, and do not use confusing word order. The subordinating conjunction “than” is often used to introduce the second element in a comparison, following an adjective or adverb in the comparative degree. Chapter 4: Writing Style and Word Usage ➤ 49 incorrect The alkyne stretching bands for the complexes are all lower than the uncoordinated alkyne ligands. correct The alkyne stretching bands for the complexes are all lower than those for the uncoordinated alkyne ligands. The alkyne stretching bands are all lower for the complexes than for the uncoordinated alkyne ligands. incorrect The decrease in isomer shift for compound 1 is greater in a given pressure increment than for compound 2. correct The decrease in isomer shift for compound 1 is greater in a given pressure increment than that for compound 2. The decrease in isomer shift in a given pressure increment is greater for compound 1 than for compound 2. ➤ Idioms often used in comparisons are “different from”, “similar to”, “identical to”, and “identical with”. Generally these idioms should not be split. incorrect The complex shows a signiﬁcantly different NMR resonance from that of compound 1. correct The complex shows an NMR resonance signiﬁcantly different from that of compound 1. incorrect Compound 5 does not catalyze hydrogenation under similar conditions to compound 6. correct Compound 5 does not catalyze hydrogenation under conditions similar to those for compound 6. exception These idioms can be split if an intervening prepositional phrase modiﬁes the ﬁrst word in the idiom. The single crystals are all similar in structure to the crystals of compound 7. Solution A is identical in appearance with solution B. 50 ➤ The ACS Style Guide ➤ Phrases such as “relative to”, “as compared to”, and “as compared with” and words such as “versus” are also used to introduce the second element in a comparison. The things being compared must be parallel. The greater acidity of nitric acid relative to nitrous acid is due to the initial-state charge distribution in the molecules. The lowering of the vibronic coupling constants for Ni as compared with Cu is due to conﬁguration interaction. This behavior is analogous to the reduced Wittig-like reactivity in thiolate versus phenoxide complexes. Correct Word Usage The words chosen by a writer are one of the deﬁning characteristics of that author’s style; however, word choice is not governed by style alone. The audience for a paper (as discussed in Chapter 3) must inﬂuence a writer’s choice of words so that the writer can select words that are likely to be known to the audience and deﬁne the words that are not. The type of document also may inﬂuence a writer’s word choices because some documents, such as scientiﬁc papers, journal articles, and books, tend to more formal word usage, whereas other documents, such as e-mails, allow less formality. The choice of the correct word to express meaning begins with a good dictionary, but it also extends to understanding small differences in meaning between two words or phrases that are almost synonymous or that are spelled similarly but have signiﬁcant differences in meaning. It is best to use words in their primary meanings and to avoid using a word to express a thought if such usage is uncommon, informal, or primarily literary. Many words are clear when you are speaking because you can amplify your meaning with gestures, expressions, and vocal inﬂections—but when these same words are written, they may be clear only to you. This chapter presents only a few words and phrases that are commonly misused in scientiﬁc writing; consult a good reference on word usage for more comprehensive assistance. (Several such references are listed under the heading “References on Scientiﬁc Communication” in Chapter 18.) Grouping and Comparison Words ➤ Use “respectively” to relate two or more sequences in the same sentence. The excitation and emission were measured at 360 and 440 nm, respectively. (That is, the excitation was measured at 360 nm, and the emission was measured at 440 nm.) Chapter 4: Writing Style and Word Usage ➤ 51 ➤ Use the more accurate terms “greater than” or “more than” rather than the imprecise “over” or “in excess of ”. greater than 50% (not in excess of 50%) more than 100 samples (not over 100 samples) more than 25 mg (not in excess of 25 mg, not over 25 mg) ➤ Use “fewer” to refer to number; use “less” to refer to quantity. fewer than 50 animals fewer than 100 samples less product less time less work ➤ However, use “less” with number and unit of measure combinations because they are regarded as singular. less than 5 mg less than 3 days ➤ Use “between” with two named objects; use “among” with three or more named or implied objects. Communication between scientists and the public is essential. Communication among scientists, educators, and the public is essential. Communication among scientists is essential. Commonly Confused Words and Phrases ➤ Choose “myself ” and “me” depending on your meaning. “Myself ” is a reﬂex- ive pronoun that is used only in sentences in which “I” is the subject, whereas “me” is used as a direct or indirect object or the object of a preposition. “Myself ” is never a substitute for “me”. Please give a copy of the agenda to Anne and me. (not to Anne and myself) I myself checked the agenda. Cheryl and I checked the agenda. (not Cheryl and myself) The agenda was checked by Barbara and me. (not by Barbara and myself) ➤ Choose “due to”, which means “attributable to”, only to modify a noun or pronoun directly preceding it in the sentence or following a form of the verb “to be”. Cutbacks due to decreased funding have left us without basic reference books. The accuracy of the prediction is due to a superior computer program. 52 ➤ The ACS Style Guide ➤ Choose “based on” and “on the basis of ” depending on your meaning. Phrases starting with “based on” must modify a noun or pronoun that usually immediately precedes or follows the phrase. Use phrases starting with “on the basis of ” to modify a verb. The doctors’ new methods in brain surgery were based on Ben Carson’s work. On the basis of the molecular orbital calculations, we propose a mechanism that can account for all the major features of alkali and alkaline earth catalyzed gasiﬁcation reactions. (not Based on …) ➤ Choose “assure”, “ensure”, and “insure” depending on your meaning. To assure is to afﬁrm; to ensure is to make certain; to insure is to indemnify for money. He assured me that the work had been completed. The procedure ensures that clear guidelines have been established. You cannot get a mortgage unless you insure your home. ➤ Choose “affect”, “effect”, and “impact” depending on your meaning. When “affect” is used as a verb, it means to inﬂuence, modify, or change. When “effect” is used as a verb, it means to bring about, but as a noun it means consequence, outcome, or result. “Impact” is a noun meaning a signiﬁcant effect. The increased use of pesticides affects agricultural productivity. The use of polychlorinated benzenes has an effect on the cancer rate. The effect of the added acid was negligible. The new procedure effected a 50% increase in yield. The impact of pesticide use on health is felt throughout the world. The acid did not have a great impact on the reaction rate. ➤ Use “whether” to introduce at least two alternatives, either stated or implied. I am not sure whether I should repeat the experiment. I am not sure whether I should repeat the experiment or use a different statistical treatment. I am going to repeat the experiment whether the results are positive or negative. Use “whether or not” to mean “regardless of whether”. incorrect I am not sure whether or not to repeat the experiment. Chapter 4: Writing Style and Word Usage ➤ 53 correct I am not sure whether to repeat the experiment. Whether or not the results are positive, I will repeat the experiment. Whether or not I repeat the experiment, I will probably leave the laboratory late tonight. ➤ Use “to comprise” to mean “to contain” or “to consist of ”; it is not a synonym for “to compose”. The whole comprises the parts, or the whole is composed of the parts, but the whole is not comprised of the parts. Never use “is comprised of ”. incorrect A book is comprised of chapters. correct A book comprises chapters. A book is composed of chapters. incorrect Our research was comprised of three stages. correct Our research comprised three stages. Use of “A” and “An” ➤ Choose the articles “a” and “an” according to the pronunciation of the words or abbreviations they precede. See pp 257 and 264 for the use of “a” and “an” with chemical elements and isotopes. a nuclear magnetic resonance spectrometer an NMR spectrometer ➤ Use “a” before an aspirated “h”; use “an” before the vowel sounds of a, e, i, o, “soft” or “short” u, and y. a house, a history (but an hour, an honor) a union, a U-14C (but an ultimate) a yard (but an ylide, an yttrium compound) ➤ Choose the proper article to precede B.A., B.S., M.A., M.S., and Ph.D., accord- ing to pronunciation of the ﬁrst letter. a B.S. degree an M.S. degree a Ph.D. 54 ➤ The ACS Style Guide Words and Phrases To Avoid ➤ Avoid slang and jargon. ➤ Be brief. Wordiness obscures your message and annoys your readers. ➤ Omit empty phrases such as As already stated It has been found that It has long been known that It is interesting to note that It is worth mentioning at this point It may be said that It was demonstrated that ➤ Omit excess words. instead of consider using It is a procedure that is often used. There are seven steps that must be completed. This is a problem that is …. These results are preliminary in nature. This procedure is often used. Seven steps must be completed. This problem is …. These results are preliminary. ➤ Write economically (and usually more precisely) by using single words instead of phrases. instead of consider using a number of a small number of are found to be are in agreement are known to be at present at the present time based on the fact that by means of despite the fact that due to the fact that during that time fewer in number for the reason that has been shown to be if it is assumed that in color, e.g., red in color in consequence of this fact in length in order to in shape, e.g., round in shape in size, e.g., small in size many, several a few are agree are now now because by although because while fewer because is if just state the color, e.g., red therefore, consequently long to just state the shape, e.g., round just state the size, e.g., small Chapter 4: Writing Style and Word Usage instead of consider using in spite of the fact that in the case of … in the near future in view of the fact that is known to be it appears that it is clear that it is likely that it is possible that it would appear that of great importance on the order of owing to the fact that prior to reported in the literature subsequent to although in …, for … soon because is apparently clearly likely possibly apparently important about because before reported after ➤ 55 ➤ Do not use contractions in scientiﬁc papers. incorrect The identiﬁcation wasn’t conﬁrmed by mass spectrometry. correct The identiﬁcation was not conﬁrmed by mass spectrometry. ➤ Do not use the word “plus” or the plus sign as a synonym for “and”. incorrect Two bacterial enzymes were used in a linked-enzyme assay for heroin plus metabolites. correct Two bacterial enzymes were used in a linked-enzyme assay for heroin and its metabolites. ➤ Do not use “respectively” when you mean “separately” or “independently”. incorrect The electrochemical oxidations of chromium and tungsten tricarbonyl complexes, respectively, were studied. correct The electrochemical oxidations of chromium and tungsten tricarbonyl complexes were studied separately. 56 ➤ The ACS Style Guide ➤ Avoid misuse of prepositional phrases introduced by “with”. poor Nine deaths from leukemia occurred, with six expected. better Nine deaths from leukemia occurred, and six had been expected. poor Of the 20 compounds tested, 12 gave positive reactions, with three being greater than 75%. better Of the 20 compounds tested, 12 gave positive reactions; three of these were greater than 75%. poor Two weeks later, six more animals died, with the total rising to 25. better Two weeks later, six more animals died, and the total was then 25. ➤ Do not use a slash to mean “and” or “or”. incorrect Hot/cold extremes will damage the samples. correct Hot and cold extremes will damage the samples. ➤ Replace “and/or” with either “and” or “or”, depending on your meaning. incorrect Our goal was to conﬁrm the presence of the alkaloid in the leaves and/or roots. correct Our goal was to conﬁrm the presence of the alkaloid in the leaves and roots. Our goal was to conﬁrm the presence of the alkaloid in either the leaves or the roots. Our goal was to conﬁrm the presence of the alkaloid in the leaves, the roots, or both. ➤ If you have already presented your results at a symposium or other meeting and are now writing the paper for publication in a book or journal, delete all references to the meeting or symposium, such as “Good afternoon, ladies and gentlemen”, “This morning we heard”, “in this symposium”, “at this meeting”, and Chapter 4: Writing Style and Word Usage ➤ 57 “I am pleased to be here”. Such phrases would be appropriate only if you were asked to provide an exact transcript of a speech. ➤ Avoid using the word “recently”. Your article or book may be available for a long time. This word will make it look dated in little time. poor It was recently found that these effects enhance the bond strength. better Harris and Harris (2006) found that these effects enhance the bond strength. Gender-Neutral Language The U.S. government and many publishers have gone to great effort to encourage the use of gender-neutral language in their publications. Gender-neutral language is also a goal of many chemists. Recent style guides and writing guides urge copy editors and writers to choose terms that do not reinforce outdated sex roles. Gender-neutral language can be accurate and unbiased and not necessarily awkward. The most problematic words are the noun “man” and the pronouns “he” and “his”, but there are usually several satisfactory gender-neutral alternatives for these words. Choose an alternative carefully and keep it consistent with the context. ➤ Instead of “man”, use “people”, “humans”, “human beings”, or “human species”, depending on your meaning. outdated The effects of compounds I–X were studied in rats and man. gender-neutral The effects of compounds I–X were studied in rats and humans. outdated Men working in hazardous environments are often unaware of their rights and responsibilities. gender-neutral People working in hazardous environments are often unaware of their rights and responsibilities. outdated Man’s search for beauty and truth has resulted in some of his greatest accomplishments. gender-neutral The search for beauty and truth has resulted in some of our greatest accomplishments. 58 ➤ The ACS Style Guide ➤ Instead of “manpower”, use “workers”, “staff ”, “work force”, “labor”, “crew”, “employees”, or “personnel”, depending on your meaning. ➤ Instead of “man-made”, use “synthetic”, “artiﬁcial”, “built”, “constructed”, “manufactured”, or even “factory-made”. ➤ Instead of “he” and “his”, change the construction to a plural form (“they” and “theirs”) or ﬁrst person (“we”, “us”, and “ours”). Alternatively, delete “his” and replace it with “a”, “the”, or nothing at all. “His or her”, if not overused, is also acceptable. Using passive voice or second person (“you”, “your”, and “yours”) also works sometimes. outdated The principal investigator should place an asterisk after his name. gender-neutral Principal investigators should place asterisks after their names. If you are the principal investigator, place an asterisk after your name. The name of the principal investigator should be followed by an asterisk. ➤ Do not use a plural pronoun with a singular antecedent. incorrect The principal investigator should place an asterisk after their name. correct The principal investigators should place asterisks after their names. ➤ Instead of “wife”, use “family” or “spouse” where appropriate. outdated The work of professionals such as chemists and doctors is often so time-consuming that their wives are neglected. gender-neutral The work of professionals such as chemists and doctors is often so time-consuming that their families are neglected. outdated the society member and his wife gender-neutral the society member and spouse ➤➤➤➤➤ CHAPTER 5 Electronic Submission of Manuscripts Using Web-Based Systems Sarah C. Blendermann E lectronic submission of manuscripts to journals is undergoing signiﬁcant change as publishers respond to mounting pressure to publish faster, better, and more efﬁciently. The use of the Web and e-mail enables the peer-review process to move more rapidly, speeding review and decision cycles. And although scientiﬁc research has always been an international activity, journal publishing is increasingly global, with authors, reviewers, and editors contributing from numerous countries and all participants beneﬁting from electronic communications. ✐ Reminder: Good practices and appropriate ﬁle creation start early in the manuscript preparation process. If author source ﬁles are not of adequate quality for production, then the publication process will be delayed. Authors should be mindful of publishers’ requirements early in the writing process. This chapter covers the major systems used by dominant commercial publishers and professional societies to manage the submission, review, and acceptance of scholarly manuscripts, and it endeavors to guide authors through the routine tasks associated with submitting a manuscript online. It is important to acknowledge that publishers will revise their systems and add new features quickly, so the information that follows will likely age rapidly. However, authors can rely on this chapter to guide them through the general process of online submission. Proprietary and commercial editorial systems are frequently designed to accommodate both electronic and paper publication processes. Capabilities vary, Copyright 2006 American Chemical Society 59 60 ➤ The ACS Style Guide but many systems have become similar as publishers establish parallel mechanisms for managing the peer-review process. Leading commercial software packages currently include Bench>Press from HighWire Press, Editorial Manager from Aries Systems, EJPress from eJournal Press, ScholarOne Manuscript Central, and Rapid Review from Cadmus Systems. Other Web-based commercial products include EdiKit from Berkeley Electronic Press; myICAAP, EPRESS, ESPERE, Fontisworks, and Open Journal Systems from University of British Columbia; PublishASAP; Temple Peer Review Manager; and Xpress Track. Each package provides authors, reviewers, and editors with submission acknowledgments, decision letters, and review documents transmitted using e-mail; no paper correspondence is needed. Several publishers have opted to develop proprietary programs rather than purchase services from a third party. Examples include the American Chemical Society’s ACS Paragon System and the American Institute of Physics’ Peer X-Press. These packages offer features and workﬂow similar to those contained in commercial editorial packages. Appendix 5-1 matches selected scientiﬁc publishers and research grant agencies with the manuscript submission software they use and manuscript submission sites. Preparing Materials The author guidelines for each journal contain generic and journal-speciﬁc instructions concerning manuscript preparation. They indicate the types of components that are required for online submissions, such as the cover letter, abstract, manuscript document, supporting information, ﬁgures, and proposed reviewers. Publishers require these items to be submitted in common word-processing or graphics formats, and author guidelines provide the technical details for preparing these manuscript components. Assembling and organizing electronic components of a manuscript in advance will streamline the process and reduce the possibility of errors in submission. The author guidelines will indicate if there are word-processing templates available for authors to download and will specify if there are requirements about their use. Template ﬁles contain all the necessary formatting for a particular journal and are provided by the publisher from its Web site. Templates make it easier to format submissions to meet the publisher’s speciﬁcations. It is important to understand why authors are asked to provide manuscripts as both word-processing and PDF ﬁles. These versions of the manuscript are used in different ways; the PDF version of a manuscript is more suitable for peer review because it is easily transferred among authors, editors, and reviewers and is readable with the ubiquitous free Adobe Acrobat Reader. PDF ﬁles are portable Chapter 5: Electronic Submission of Manuscripts ➤ 61 across computer platforms, whereas original word-processing ﬁles may not be compatible with the system of an editor or reviewer. Publishers may require that authors submit a PDF ﬁle, or they may automatically generate one as part of the online submission process. A PDF ﬁle assists in maintaining control of versions of the manuscript because editors, authors, and reviewers can insert comments and notes for correction without altering the original text. Most publishers will require word-processing (or TeX or its derivatives) ﬁles for production purposes. These versions of the manuscript are manipulated during the ﬁnal electronic creation of a journal for publication online or in print. ✐ Reminder: Most publishers require both PDF and word-processing versions of a manuscript to be used for peer review and publication production, respectively. Another critical element of your submission is the ﬁgures associated with the manuscript. Graphics should be high-resolution and of good quality to ensure clarity and accuracy in the ﬁnal published copy and to facilitate any needed reduction required in the print publication (see Chapter 15 for more detail on preparing illustrations). Many software programs—including PowerPoint, Word, Excel, and WordPerfect—do not create high-resolution images suitable for publication. For that reason, it is recommended that authors create graphics using applications that can prepare ﬁgures in TIFF or EPS formats. Figures should have clear, sharp lines, should be clearly labeled, and should be at a high enough resolution that they can be used to compose the print journal. Appendix 5-2 presents the text and image formats accepted by seven major manuscript peer-review and submission systems. Beginning Your Submission Depending on the publisher, authors may be asked to e-mail the prepared manuscript to the editor, to upload it via an FTP server, or to upload ﬁles through the publisher’s Web browser to a secure Web site using HTTP protocol. It is extremely important to submit manuscripts in the method designated for that particular journal because submission mechanisms may vary, even within one publisher’s journals. If the journal requires online manuscript submission, submit all ﬁles to that Web site. Similarly, if the journal uses FTP or e-mail, follow the instructions carefully and send all manuscript components via the same route, unless indicated otherwise. When authors are asked to e-mail the manuscript directly to an editor, pay particular attention to the type of ﬁles authors are asked to provide, and note 62 ➤ The ACS Style Guide if the manuscript should be provided in the body of the e-mail or as an attachment. Publishers offering an FTP server for author use will have detailed instructions on how to access the FTP server. Authors may be asked to compress ﬁles when transmitting manuscripts by e-mail, FTP, or as part of an online submission system. If so, the publisher’s Web site will detail the acceptable formats for compressed ﬁles. These may include zipped, tarred, uuencoded, or BinHex ﬁles. Under some circumstances, Web uploads will automatically invoke a compression process. Leading online submission packages Bench>Press, Editorial Manager, EJPress, Manuscript Central, and Rapid Review, as well as the ACS Paragon System and the American Institute of Physics’ Peer X-Press all use the author home page. This simple online proﬁle contains the author’s contact details and establishes a user name and password. The e-mail address entered here must be correct; a typo could delay important e-mail notiﬁcations about acceptance or requests for revision. If the author has already established an account, future submissions can begin with the author login. Several publishers have adopted the concept of a submitting agent or a second author if someone other than the author is submitting the manuscript on the author’s behalf. This person is responsible for the tasks associated with submission, but correspondence and requests for further changes are made to the party designated as the corresponding or primary author of the manuscript. Submitting agent accounts are created similarly to author accounts, but they require information about the primary author also to be added to the user account proﬁle. Passwords to either author accounts or submitting agent accounts should not be shared. Doing so leaves the account holder at risk of incomplete submissions being changed or new submissions being created under his or her name. The Author Home Page After logging in, the author is presented with his or her home page. Typically, the author home page is divided into several areas; from this location, authors can begin a new submission, check the status of a previous submission, continue a submission begun earlier, or submit a revised manuscript. The author home page also shows the progress of accepted manuscripts through the production cycle to publication. As publishers increasingly recognize the value of this author home page, new features are likely to be added. In the case of the Cadmus Rapid Review software, the author home page has already evolved to include a scientist’s activities as both a referee and an author. ✐ Reminder: If an author home page is available, use it to submit new articles and to track the status of current submissions. Chapter 5: Electronic Submission of Manuscripts ➤ 63 Submitting Your Manuscript Preparing materials in advance allows the authors either to complete their full submissions in one sitting or to partially complete the process, depending on individual preferences and the requirements of the publisher. E-mail and FTP submissions require the submission to be completed at one time. However, more publishers with online submission sites allow authors to interrupt their online submissions and to complete them later. During a partial submission, each step must be completed for the information pertaining to that submission step to be saved. The author can complete the submission by logging into the journal site and accessing his or her author home page. After selecting the link for that manuscript, the submission process can be resumed, beginning with the ﬁrst incomplete step. Before the manuscript is submitted, authors are asked to review all the component parts and make any ﬁnal changes. Supplemental information should also be reviewed and validated. Crystallographic information ﬁles (CIFs) in particular can be veriﬁed using the free CheckCIF utility, which is available from the International Union of Crystallography. Usually in the cases of e-mail, FTP, or online submission, no additional changes to the manuscript or associated documents are permitted after submission unless an editor requests a revision or the publisher contacts the author to ﬁx a problem. Submitted Manuscripts After the submission is complete, the author typically receives an e-mail acknowledging the submission from either the editor or the submission system. If the publisher offers an author home page, the status of the manuscript can be tracked from that site. These sites also notify authors by e-mail as the status of the manuscript changes. If the publisher makes use of an online system for submission, the editors for that publisher may be able to use features available only to them to shepherd the manuscript through the peer-review process. In these cases, the system notiﬁes the editor of newly arrived manuscripts, allows the editor to view all associated ﬁles and details of the submission, and allows for the manuscript to be assigned to the appropriate editors and reviewers. Many systems generate the correspondence that accompanies the notiﬁcation of editors, reviewers, and authors. As decisions are made and correspondence is sent, the corresponding status changes for the manuscript are displayed on the author home page. Additional details about the peer-review process can be found in Chapter 6. Stops Along the Way (Revisions) When a revision of the paper is requested, an e-mail from the editor will detail the necessary changes. Where FTP or direct-to-editor e-mail is the preferred sub- 64 ➤ The ACS Style Guide mission mechanism, the author will send revised ﬁles directly to the indicated e-mail address or FTP location. For publishers with author home pages, authors can view the status of submitted manuscripts and determine that a revision has been requested. From the author home page, authors access the submission and upload revised manuscript documents, images, and associated ﬁles. During the submission of the revision, authors may also provide rebuttal information or revision details to clarify how the manuscript has been altered. If an author determines that a revision is necessary before a request is made by the editor, authors using Web-based submission systems must contact the appropriate editor and request that the status of the manuscript be changed within the system to indicate that a revision is needed. This step will allow the author to adjust and replace ﬁles and then to submit a revision. Once the revision is received, an acknowledgment is sent by e-mail, and the author will not be able to make further changes to the paper unless the editor requests another revision to the manuscript. Acceptance Authors can expect to be notiﬁed of their manuscripts’ acceptance by e-mail. Accepted manuscripts are copyedited and formatted according to speciﬁc journal style, using the original word-processing ﬁles from the author’s online submission. As the manuscript progresses through the various stages of production, the status on the author home page changes to reﬂect each new step. ➤➤➤➤➤ APPENDIX 5-1 Online Submission at Selected Scientiﬁc Publishers and Research Grant Agencies This appendix contains a list of scientiﬁc publishers and research grant agencies, along with the software they use for online manuscript submission and the manuscript submission site, if there is one. Table 5A-1. Scientific Publishers Publisher American Academy of Forensic Science American Association for Clinical Chemistry American Association of Pharmaceutical Scientists American Chemical Society American Geophysical Union American Institute for Chemical Engineers American Institute of Physics Software Information and forms only Bench>Press URL No electronic submission Editorial Manager Pharmaceutical Research submissions at https://www.editorialmanager.com/ pharmres/ https://paragon.acs.org/paragon/index.jsp ACS Paragon System Geophysical Electronic Manuscript System Rapid Review Some journals use Peer X-Press American Mathematical Society American Peptide Society American Pharmacists Association Information and forms only ScholarOne Manuscript Central ScholarOne Manuscript Central American Physical Society American Society for Biochemistry and Molecular Biology — — http://submit.clinchem.org/?ctst=y http://gcubed-submit.agu.org/ https://www.rapidreview.com/AIChE2/ CALogon.jsp http://www.aipservices.org/peerxpress/ index.html After acceptance, you will be asked to use their FTP or e-mail site at http://www.aip. org/epub/submittext.html. No electronic submission http://bip-pep-wiley.manuscriptcentral.com/ Journal of Pharmaceutical Sciences submissions at http://jpharmsci-wiley. manuscriptcentral.com/ http://publish.aps.org/ESUB/ The Journal of Biological Chemistry submissions at http://osrs.jbc.org/asbmb/osrs. nsf/StartSubmission?OpenForm Continued on next page 65 66 ➤ The ACS Style Guide Table 5A-1. Scientific Publishers—Continued Publisher American Society for Cell Biology American Society for Mass Spectrometry American Society for Microbiology Biophysical Society Blackwell Publishing Cambridge University Press Electrochemical Society Elsevier Software EJPress URL http://www.mbcpapers.org/ Elsevier author gateway Rapid Review http://authors.elsevier.com/JournalDetail. html?PubID=505727&Precis=DESC https://www.rapidreview.com/ASM2/ CALogon.jsp http://submit.biophysj.org/?ctst=y No electronic submission Bench>Press Information and forms only Information and forms only Peer X-Press Elsevier author gateway Institute of Electrical & Electronics Engineers (IEEE) — Institute of Food Technologists Materials Research Society Nature ScholarOne Manuscript Central ScholarOne Manuscript Central EJPress Oxford University Press Some journals use ScholarOne Manuscript Central Royal Society of Chemistry Science ReSourCe Society of Plastics Engineers Society of Toxicology Information and forms only ScholarOne Manuscript Central Information and forms only Some journals use ManuscriptXpress Taylor & Francis Wiley-VCH Wolters Kluwer/Springer World Scientific Submit to Science ScholarOne Manuscript Central No electronic submission http://jes.peerx-press.org/cgi-bin/main.plex Each journal has its own instructions for submitting work. Go to the home page of your journal of interest at http://authors. elsevier.com/. Each journal has its own instructions for submitting work. Go to the home page of your journal of interest at http://www.ieee. org/organizations/pubs/guide.html. http://ift.manuscriptcentral.com/ http://jmr.manuscriptcentral.com/ http://npg.nature.com/npg/servlet/ Content?data=xml/05_sub. xml&style=xml/05_sub.xsl Each journal has its own instructions for submitting work. Go to the home page of your journal of interest at http://www3.oup. co.uk/jnls/. http://chemistry.rsc.org/Publishing/ ReSourCe/ http://www.submit2science.org/ws/menu. asp No electronic submission http://toxsci.manuscriptcentral.com/ No electronic submission Each journal has its own instructions for submitting work. Go to the home page of your journal of interest. Each journal has its own instructions for submitting work. Go to the home page of your journal of interest at http://www. kluweronline.com. Each journal has its own instructions for submitting work. Go to the home page of your journal of interest at http://www. worldscinet.com/subject.shtml. Chapter 5: Electronic Submission of Manuscripts ➤ 67 Table 5A-2. Research Grant Agencies Research Grant Agency Alexander von Humboldt Stiftung Software Information and forms only URL No electronic submission http://www.humboldt-foundation.de/ en/programme/bewerbung.htm American Chemical Society Petroleum Research Fund — Electronic submission only. http://www.chemistry.org/prf American Heart Association — Electronic submission only. http://www.americanheart.org/ presenter.jhtml?identifier=270 https://home.heart.org/resch/ Australian Research Council Grant Application Management System (GAMS) Electronic submission only. https://gams.arc.gov.au/ Camille and Henry Dreyfus Foundation Limited online submission http://www.dreyfus.org/index.shtml Ford Foundation Diversity Fellowships NRCOnline http://nrc58.nas.edu/nrconline/ford/ login/Login.asp NASA NASA Solicitation and Proposal Integrated Review and Evaluation System (NSPIRES) http://nspires.nasaprs.com/external/ The National Academies, Research Associateship Programs NRC WebRAP http://nrc58.nas.edu/nrcwebrap/rap/ login/Register.asp National Institutes of Health, Office of Extramural Research Information and forms only No electronic submission http://grants1.nih.gov/grants/oer.htm National Science Foundation FastLane https://www.fastlane.nsf.gov/fastlane. jsp Office of Naval Research Information only No electronic submission http://www.onr.navy.mil/02/how_ to.asp proposalCENTRAL Research and Management System (RAMS) https://v2.ramscompany.com/ U.S. Air Force Office of Scientific Research Information and forms only No electronic submission http://www.afosr.af.mil/ U.S. Department of Energy, Office of Science PureEdge http://www.science.doe.gov/grants/ Welch Foundation Information and forms only No electronic submission http://www.welch1.org/ Wellcome Trust eGrants http://www.wellcome.ac.uk/node2110. html or http://www.wellcome.ac.uk/ doc_WTD004053.html ➤➤➤➤➤ APPENDIX 5-2 Key Features of Selected Online Submission Systems The following systems are entirely Internet-based and incorporate all elements of submission, review, and manuscript management, unless otherwise noted. They operate with standard browsers and require that authors, editors, and reviewers have Adobe Acrobat Reader to view PDF documents. Authors, reviewers, and editors are offered a secure, password-protected login. Each system incorporates an author home page for the submission, revision, and tracking of manuscripts. Similarly, each system allows referees to submit reviews of manuscripts online. Publishers modify these systems in varying degrees to reﬂect different workﬂows. For this reason, journals using the same software may have slightly different features. This list indicates acceptable submission ﬁle types for each system and highlights the system’s distinctive features. As technology changes and new features become available, publishers will amend submission sites and systems. Therefore, authors should check regularly for current requirements with the journal before beginning a manuscript submission. Table 5A-3 catalogs a variety of scientiﬁc publishers and the systems they currently use to accept manuscripts online. This table is not all-encompassing, but it is intended to be representative of publishing organizations that contribute to the peer-review literature used by ACS members. 68 Chapter 5: Electronic Submission of Manuscripts 69 ➤ Table 5A-3. Text and Image Formats Acceptable to Different Web-Based Manuscript Submission Systems Format Text Formats MS Word (.DOC) WordPerfect (.WPD) Encapsulated PostScript (.EPS) PostScript (.PS) Text—ASCII (.TXT) Rich text format (.RTF) TeX LaTeX Portable document format (.PDF) Image Formats Graphics interchange format (.GIF) Joint Photographic Experts Group (.JPEG) Tagged image file (.TIF) Encapsulated PostScript (.EPS) PostScript (.PS) MS PowerPoint (.PPT) Other Acceptable Formats Chemical markup language (.CML) Chemical structures, such as those created by ChemDraw, ChemSketch, ISIS/Draw DrawIt (formerly Chemwindow) Crystallographic information file (.CIF) Executable (.EXE) MS Excel (.XLS) MOL Video files, such as QuickTime (.AVI, .MPEG) Protein Data Bank (.PDB) Windows metafile (.WMF) Winzip file (.ZIP) ACS Paragon System Bench> Editorial Press Manager EJPress Manuscript Central Peer X-Press Rapid Review Yes — Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes — — Yes Yes — Yes Yes Yes — — — — — — Yes Yes Yes Yes Yes Yes Yes Yes — Yes — — Yes Yes Yes Yes Yes Yes Yes Yes — Yes — — — — — — — — Yes Yes Yes Yes Yes Yes — Yes Yes Yes Yes Yes Yes — Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes — Yes — — — Yes — — Yes — — Yes Yes — Yes Yes — Yes Yes — Yes — Yes a b b a b a b Yes Yes Yes — Yes — Yes Yes Yes Yes — Yes — Yes Yes Yes Yes — Yes — Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes — — — — Yes Yes Yes Yes — — — — Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes Yes — — — — Yes Yes Yes Yes — — — — Yes Yes Yes Yes Note: The systems and their developers are as follows: ACS Paragon System, American Chemical Society; Bench>Press, HighWire Press; Editorial Manager, Aries Systems; EJPress, eJournal Press; Manuscript Central, ScholarOne; Peer X-Press, American Institute of Physics; and Rapid Review, Cadmus Systems. a These systems allow a variety of designated file types to be uploaded as supplemental information. b These systems allow any file type to be uploaded as supplemental information. ➤➤➤➤➤ CHAPTER 6 Peer Review Barbara A. Booth P eer review is a process used by scientiﬁc publications to assist editors in evaluating manuscripts, particularly for scientiﬁc merit. It is not the only system used to evaluate manuscripts, and it is not perfect. Editors of peer-reviewed books and journals send manuscripts to several reviewers and request their opinions on originality and scientiﬁc importance of the topic, the quality of the work performed, and the appropriateness for the speciﬁc journal. Reviewers may also comment on language usage, clarity of ﬁgures and tables, manuscript length, and anything that they ﬁnd relevant to effective communication. Although not every editor uses peer review in the same manner, this chapter presents a summary of many common attributes of the peer-review process. (For a broader discussion of peer review, see “Peer Review and the Acceptance of New Scientiﬁc Ideas” at http://www.senseaboutscience. org.uk/PDF/peerReview.pdf.) Purpose of Peer Review When a manuscript is submitted for consideration, peer review provides the editor with advice on whether to accept the manuscript for publication. Reviewers also provide suggestions for improving the manuscript. The decision on whether to accept the manuscript for publication rests solely with the editor. Reviewers provide additional expertise and have perspectives that may complement that of the editor. Customarily, peer review is anonymous: the identities of reviewers are not revealed by editors. Some journals also hold authors’ names and afﬁliations in conﬁdence, a double-blind review approach. Occasionally, reviewers request Copyright 2006 American Chemical Society 71 72 ➤ The ACS Style Guide that the editor disclose their names to authors; this is allowed at the discretion of the editor, based on the policy of the individual publication. In one variation of the peer-review process, review is not anonymous; all reviewers are identiﬁed. Peer review is also intended to help authors. External review can help improve the presentation and interpretation of data alike, and ultimately, the research. Clearly and succinctly describing a scientiﬁc study is challenging, and reviewers provide valuable feedback. Few manuscripts are so well written that they are accepted without revision. Data and interpretation that seem clear to authors are not always comprehensible to readers. Scientiﬁc research is both competitive and cooperative; at its best, peer review is a part of the cooperative process. For example, after evaluating data, a reviewer may suggest an alternative explanation or additional experiments that trigger ideas for further research. Also, a reviewer pointing out an error can save an author the embarrassment of subsequently publishing a correction. The Peer-Review Process When the editor receives a manuscript, he or she examines it and determines whether the manuscript ﬁts within the scope of the journal, whether it meets the speciﬁc requirements of the journal, and whether it is of sufﬁcient scientiﬁc merit for consideration. Not all manuscripts are transmitted to reviewers. In some cases, the editor decides to reject a manuscript without review, or rarely, to accept it for publication. Manuscripts are rejected without review for various reasons, including the following: the topic is inappropriate for the journal; the concept or the data are not novel; the format is incorrect; the writing is so poor that the manuscript is unreadable; or the authors have previously published overly similar papers. If a manuscript is rejected without review, the editor will usually brieﬂy inform the author of the reason. Some editors offer suggestions to help authors with future submissions. If the editor decides to send the manuscript for peer review, customarily two to four individuals with appropriate expertise—training or research experience—are asked to review the manuscript. The editor may identify reviewers in a number of ways. Many editors ask authors to recommend reviewers; some do not. Author-recommended reviewers may or may not be used. Most editors will not send manuscripts to speciﬁc reviewers if an author so requests. Other potential reviewers may be authors cited in the manuscript, acknowledged experts in the ﬁeld, or other active researchers in the ﬁeld. Editors often use scientiﬁc search services (such as SciFinder or SciFinder Scholar for chemists) to identify qualiﬁed potential reviewers. Reviewers may or may not be known personally to the editor. Most journals maintain records on thousands of reviewers, including their expertise, manuscripts they have reviewed, performance, and so on. Chapter 6: Peer Review ➤ 73 Usually, reviewers are asked whether they are willing to review a manuscript. If they agree, the manuscript is provided in either hard copy or electronically, often with an accompanying review form. Editors generally ask reviewers to submit their reviews in two or three weeks. When a review is overdue, the editor usually sends a reminder to the reviewer. Once reviews are returned, the editor reads the reviews in conjunction with the relevant manuscript, evaluating both the manuscript and the reviews, and then makes a decision whether to accept the manuscript, request revisions, reject the manuscript, or send it for additional review. In some cases of conﬂicting advice or opinions of reviewers, editors may seek advice from others. Editors are not obligated to follow the recommendations of reviewers. Reviewer ratings are not averaged; often, a single cogent negative review leads to rejection of a manuscript. Responsibilities of Reviewers Peer review is a critical component of formal scientiﬁc communication, and every scientist has an obligation to do a fair share of reviewing. ✐ Reminder: Manuscripts should be reviewed in a timely and balanced manner and should be kept conﬁdential until publication. When a manuscript is under review, it is a conﬁdential document and it should not be discussed or shown to others. After reading a manuscript, a reviewer may conclude that a better review could be accomplished with assistance from a colleague. In this circumstance, the reviewer should inform the editor before engaging the colleague. Reviewers are expected to provide reviews that are thorough and unbiased. A reviewer in direct competition with the authors of a manuscript should inform the editor that there is a potential conﬂict of interest and discuss the issue with the editor. In addition, if reviewers are asked to review the work of someone at the same institution or the work of a previous student or co-worker, the reviewer should inform the editor. In some cases, the editor will excuse the reviewer from doing the review; in other cases, the editor will consider the relationship when evaluating the review. Reviewers are expected to submit their reviews on time. Most reviewers are also authors and expect reviews of their manuscripts to be handled expeditiously. If circumstances arise that prevent or delay a review, the editor should be informed as soon as possible. The entire manuscript should be read carefully and critically. Most reviewers read a manuscript more than once. Manuscripts should be rated on technical quality, signiﬁcance of the work, importance to the research ﬁeld, and adequacy of expression. Often a standard form is provided for this portion of the review. 74 ➤ The ACS Style Guide ➤➤➤➤➤ Box 6-1. Suggested Topics for a Peer Review Are the methods (experimental section) adequately described and referenced? Are there any unsupported conclusions? Is there anything that is confusing or ambiguous? Do ﬁgures and tables appropriately illustrate the data? Is the introduction clear and informative? Is either the introduction or discussion longer than necessary, and do they make sense in relation to the subject and the data? Although the discussion is the appropriate place for speculation, is it excessive? Are the appropriate references cited? Are the references accurate? Is English usage and grammar adequate? Some reviewers may be inclined to edit or annotate the manuscript. However, reviews are more valuable to editors if reviewers mention that there are problems with the English and concentrate on evaluating the data and its interpretation. Is the length of the manuscript unwarranted? Suggestions on how a manuscript can be shortened are appreciated by editors. Is the use of color warranted? Printing color is a signiﬁcant expense for the publisher. Reviewers should feel free to comment on the suitability of the manuscript for the particular publication. Sometimes ﬁrst-rate manuscripts are submitted to an inappropriate publication. In addition to the actual review, some editors allow reviewers to submit conﬁdential comments about the manuscript. These are not forwarded to the author. If suspicions of abuse, plagiarism, or fraud arise, the editor should be informed immediately. Many reviewers divide their reviews into general comments and speciﬁc, detailed comments. In the general section, reviewers should draw attention to both the strong and the weak points of the manuscript, the concepts, the objectives, and the methods. Like an author writing a manuscript, reviewers should write reviews in a comprehensive but concise manner, addressing the questions presented in Box 6-1. Reviews should be written in a helpful, tactful manner. Editors generally edit or do not pass discourteous comments to authors. Abusive reviews lack credibility and also reﬂect poorly on the reviewer. Chapter 6: Peer Review ➤ 75 Responsibilities of Authors Authors should read the current instructions to authors for the publication to which they intend to submit a manuscript. For journals, these instructions are typically published in the ﬁrst issue of the year and can often be found on the Web. Author guidelines for books are available from the publisher, and sometimes they are posted on the publisher’s Web site. Many submissions are rejected without review because the manuscript does not conform to the publication guidelines. ✐ Reminder: Authors should read the current instructions to authors for any publication to which they intend to submit a manuscript. If English is not the author’s native language, it is a good idea to ask a native English speaker to edit the manuscript before submission. Alternatively, authors can employ a technical editing service. Such editing services can be found through recommendations from colleagues, by searching the Web, or advertised in scientiﬁc publications. However, it is the author’s responsibility to ensure that the writing is accurate. In suggesting potential reviewers, authors should not recommend members of their own institution or current or recent collaborators (including students or postdoctoral associates). Many authors suggest the names of eminent scientists in their ﬁelds. These individuals are frequently asked to review a large number of manuscripts and, constrained by time, may not be available to review additional manuscripts. Therefore, it is more helpful to suggest the names of highly qualiﬁed, less well known researchers. Many book and journal editors also allow authors to request that certain individuals, such as those in direct competition, not be selected to review. Editors usually comply with these requests. Authors should read reviews carefully and dispassionately, with the expectation that reviewers’ comments will improve their manuscripts. When an editor requests a revision, authors should respond to all comments and answer all questions. Editors generally reject perfunctory revisions. When it is apparent that a reviewer has misread or misinterpreted the text, authors should provide a direct but tactful reply. Revisions should be submitted in a timely manner. Generally, editors expect revisions within a few weeks, not months. If there is long delay in submitting a revision, some editors will consider the revision to be a new manuscript. Sometimes an editor or reviewer will ask authors to perform additional experiments or to reanalyze data, necessitating a delay in submitting a revision. Authors should ask the editor for an extension, if necessary, providing an explanation. When a manuscript is rejected, authors should read the editor’s letter and reviews carefully to determine the reasons for the rejection. Rejection usually 76 ➤ The ACS Style Guide means that another publication should be considered for submission of the manuscript. Some manuscripts should be abandoned. Although some editors will consider an appeal of a rejection, successful appeals are rare. Only if authors are conﬁdent that with the help of the reviews, the research and its presentation can be improved, should they resubmit the manuscript to the same publication. A cover letter accompanying the revision of the rejected manuscript should describe all changes to the manuscript, reply to all reviewer comments, and respond to all questions. Ultimately, whether the manuscript is submitted to a different publication, revised and resubmitted to the same publication, or further experiments are performed to broaden the scope of the investigation, critical assessment from reviewers can aid both research and its communication. Encouragement to New Investigators The peer-review process may seem daunting and at times unfair to new investigators. On occasion, reviewers will be unduly critical and unhelpful—and infrequently, outright nasty and rude. Sometimes reviewers can be exasperatingly slow. Good manuscripts are rejected, in particular by prestigious journals, which receive many more high-quality manuscripts than they can publish. However, many reviewers and editors will be solicitous and encouraging to investigators in the early stages of their careers. Despite its shortcomings, peer review is regarded by the scientiﬁc community as an essential component to high-quality, effective communication that further advances science. ✐ Reminder: Frequently consult the “Ethical Guidelines to Publication of Chemical Research” (Appendix 1-1 in this book, or on the Web at https:// paragon.acs.org). The guidelines are reviewed regularly to ensure their clarity. ➤➤➤➤➤ CHAPTER 7 Copyright Basics Karen S. Buehler, C. Arleen Courtney, and Eric S. Slater C opyright law is a cornerstone of intellectual and scientiﬁc exchange. This chapter is intended to introduce a complex and constantly changing legal area; we do not intend to provide legal advice. The ﬁrst section is an overview of U.S. copyright law: what materials are subject to copyright, who owns copyright, and when copyrighted materials may be used by others. The second part of the chapter presents the methods of obtaining permission to use someone else’s copyrighted work. The third part brieﬂy explains how copyright is transferred from the author to the publisher. U.S. Copyright Law What Can Be Copyrighted Copyright is a doctrine of federal law (Title 17, U.S. Code) and is deﬁned as a form of intellectual property law that protects original works of authorship ﬁxed in a tangible medium of expression for a speciﬁed period of time. A tangible medium of expression is something that can be seen, touched, or heard (see the examples below). Copyright applies to all media of expression, including print, the Internet, CD-ROM, and videotape. Copyright allows authors and creators certain rights to protect their original works. Copyright law protects both published and unpublished works. The authors wish to thank Barbara F. Polansky and William J. Cook for their time in reviewing and commenting on this chapter. Copyright 2006 American Chemical Society 77 78 ➤ The ACS Style Guide Copyright applies to a variety of works including the following: • • • • • • • • • literary works (including scientiﬁc works and computer programs); musical works (including lyrics); dramatic works (including accompanying music); pantomimes and choreographic works; pictorial, graphic, and sculptural works; motion pictures and other audiovisual works; sound recordings; architectural works; and compilations and databases to the extent that they reﬂect originality in the selection and arrangement of elements. What Cannot Be Copyrighted Copyright does not protect the following: • Works not ﬁxed in a tangible form of expression. Copyright does not protect ideas, only the ﬁxed expression of ideas. Thus a thought, not written down in any way, is not protected. • Titles, names, short phrases, slogans, familiar symbols, or designs. (These items may be protected under trademark or service mark laws.) • Lists of ingredients, contents, or facts. • Ideas, procedures, methods, systems, processes, concepts, principles, discoveries, and devices. (These items may be protected under patent law.) • Standard calendars, rulers, lists, or tables taken from the public domain and other works containing no original authorship. Who Owns the Copyright The copyright owner is the author or creator of the original work. An original work can be in the form of an article, photograph, illustration, ﬁgure, table, etc. Copyright does not protect ideas, only the actual expression of the ideas. Therefore, the copyright owner is the person who drew a ﬁgure or table on a computer and saved it, or took a photograph (the subject of the picture is not the copyright owner), or wrote a narrative on a piece of paper. There are two exceptions when the author or creator of the original work is not the copyright owner: (1) when the copyright was transferred in writing to another person or entity (usually via a copyright status form) and (2) when the work was created as a work-made-for-hire. In a work-made-for-hire situation, employees create the work within the scope of their employment; therefore, the copyright owner is the employer. The employer may be an individual, corporation, or university. The above two examples represent typical scenarios when publishing scientiﬁc or scholarly works. Work-made-for-hire can also cover, among other speciﬁed categories, independent contractor situations under certain conditions and if the parties have agreed in writing. Chapter 7: Copyright Basics ➤ 79 Box 7-1. Copyright at ACS Each division of the ACS is responsible for copyright issues related to material that appears in its publications. The ACS Copyright Ofﬁce can assist ACS authors and editors with copyright issues pertaining to materials published by the ACS Publications Division. The e-mail address is copyright@acs.org. The mailing address is American Chemical Society, Copyright Ofﬁce, 1155 Sixteenth Street, NW, Washington, DC 20036. The fax number is 202-776-8112, and the telephone number is 202-872-4368 or 4367. Contact other ACS divisions directly for permission to use their material. For speciﬁc advice regarding copyright matters, it is best to seek legal counsel. Rights of the Copyright Owner The copyright owner can be described as controlling a “bundle” of stated rights. The copyright owner (whether an individual, a corporation, or a publisher) retains certain exclusive rights in the work. The bundle of rights includes • • • • reproducing copies of the work; distributing copies of the work to the public; creating derivative works based on the work; performing the work publicly (for certain types of works) and, in the case of sound recordings, by digital audio transmission; and • displaying the work publicly (for certain types of works). Most scientiﬁc and scholarly publishers require authors (or their employers) to transfer copyright as part of their publication agreement. The ACS Publications Division requires authors (or their employers) to transfer copyright to the American Chemical Society, although some rights are transferred back to the authors (or their employers). For speciﬁc information regarding transferring copyright to ACS and authors’ rights, see http://pubs.acs.org/copyright_info. html or contact the ACS Copyright Ofﬁce (see Box 7-1). Copyright Notice A work is protected by copyright even if it does not contain a formal copyright notice (the word “copyright”, abbreviation “copr”, or symbol © with the year of ﬁrst publication and name of copyright owner). It is strongly recommended to place a copyright notice in or on a work, thereby giving notice that someone controls the rights to that work. Registration of a work with the U.S. Copyright Ofﬁce is not necessary to obtain copyright protection, although there are substantial 80 ➤ The ACS Style Guide beneﬁts to doing so. For more information about copyright registration, contact the U.S. Copyright Ofﬁce at 202-707-5959, or at http://www.copyright.gov/. The U.S. copyright law also provides remedies for infringement. Authors should contact the appropriate book or journal editor in cases where they believe their work has been infringed upon. If a copyright owner (in the case of an ACS publication, the ACS) believes that his or her work has been infringed upon, it is the responsibility of the copyright owner to bring action. Fair Use The U.S. copyright law contains limitations on rights granted to the copyright owner. Probably one of most misunderstood of these limitations is fair use. Essentially, fair use permits certain actions that might otherwise infringe upon an exclusive right of the copyright owner. It has been our experience that the interpretation of what constitutes fair use can vary widely. For instance, a copyright owner’s interpretation may be very narrow; a party looking to take advantage of fair use will interpret it broadly. Using excerpts from works for the following purposes may qualify as fair use: • criticism or comment; • news reporting; • teaching (but only in a spontaneous situation. If one knows in advance that copyrighted material will be used in a class, permission must be obtained.); and • scholarship or research. (Private researchers and nonproﬁt employees may make one photocopy of an article for their own research purposes only.) These uses may not constitute copyright infringement. The determination of whether a use is fair depends on the facts in each case. Even if the facts are virtually identical, one degree of minutiae can cut against fair use. The U.S. copyright law provides four factors that must be considered in determining whether any particular use is fair use. Courts weigh the four factors against each other, and no one factor is determinative in every case. The four factors are the following: 1. the purpose and character of the use, including whether it is of a commercial nature or for nonproﬁt educational purposes; 2. the nature of the work; 3. the amount and substantiality of the portion used in relation to the work as a whole; and 4. the effect of the use in question on the potential market for or value of the work. There are no numerical guidelines or percentages that can be used for each situation where fair use might be involved. Even one percent of a work used in a Chapter 7: Copyright Basics ➤ 81 manuscript may be determined to be against fair use if the material is considered the most important part or the heart of that work. Fair use is a defense, and a strong argument must be made that the use is actually fair. Never assume that a use is a fair use; it is always best to seek permission to avoid potential and sometimes costly problems. ✐ Reminder: Never assume that a use is a fair use; it is always best to seek permission to avoid potential problems. Public Domain and U.S. Government Works Works that are in the public domain are not protected by copyright. The following are situations in which a work can have public domain status: 1. works published before 1923 whose copyright term has expired (see the section called “Duration of Copyright”), or works for which copyright was not renewed; 2. works published before 1978 without a proper copyright notice; 3. works dedicated to the public domain by their creator, e.g., so-called shareware; and 4. works authored by U.S. government employees within the scope of their employment. Generally, it is not necessary to seek anyone’s permission to use public domain works. However, when using material that appeared in a U.S. government publication, check the caption or reference section to see if credit is given to a source for which permission is required. ✐ Reminder: Even though material in a U.S. government publication generally does not require permission to reproduce it, sometimes government publications include material that is protected by copyright. Always check the caption or reference section to determine whether you need to obtain permission to reproduce it. Common Misconceptions about Copyright One misconception about copyright status involves material found on Internet Web sites. Someone does own copyright to the material on a Web site, and it is necessary to obtain permission to reuse it. The lack of a copyright notice does not mean that the work is not protected, nor does it mean that a work is in the public domain or that the author of the work has waived his or her rights. Other misconceptions involve photographs. The individuals appearing in photographs are not the copyright owners. The photographer, or employer if 82 ➤ The ACS Style Guide the photo is a work-made-for-hire, is the copyright owner, and permission to reuse a photograph must come from the copyright owner. (Permission of people appearing in photographs may also be required by a publisher, but this is not a copyright issue. It is a privacy/right of publicity concern.) Another problem involves the use of photographs of old works of art. It may be true that the art itself is in the public domain (i.e., a van Gogh or Michelangelo painting). However, the photograph of the artwork is protected by copyright. In these cases, the copyright owner may not be an individual photographer but a museum or a historical society. Duration of Copyright Under current U.S. copyright law, length of copyright is life of the author plus 70 years. For works-made-for-hire, length of copyright is 95 years from the date of ﬁrst publication, or 120 years from the date of creation, whichever is shorter. Copyright in the Electronic Age Several recent court cases have involved copyright infringement in electronic media. The legal disputes centered on which party controlled speciﬁc rights under the contractual arrangements authors had with publishers. A common thread to these cases is whether a publisher controls all rights to publish content in any format. Publishers and authors need to be aware of the rights they hold, either explicitly under the U.S. copyright law, or via a licensing arrangement. ACS requires complete transfer of copyright in all formats, thus allowing ACS to publish material in different formats. In cases where authors do not transfer copyright, publishers generally require a nonexclusive licensing arrangement. Here, the author retains copyright and grants certain rights to the publisher. Placing material on the Internet without authorization from the copyright owner is a copyright infringement, even if the publisher had permission to use the material in print. It is important to have a working knowledge of copyright law, and it is helpful to have some familiarity with contracts. Publishers and authors need to read contracts and copyright transfer forms thoroughly before signing and be certain that they understand what they are agreeing to. There are numerous Web sites containing copyright information. We recommend the following Web sites for accurate and up-to-date information, although this is by no means a complete list: • U.S. Copyright Ofﬁce, http://www.copyright.gov/ • Association of American Publishers, http://www.publishers.org/ • American Chemical Society Copyright Learning Module, http://pubs.acs. org/copyright/learning_module/module.html Chapter 7: Copyright Basics ➤ 83 Obtaining Permission To Reproduce Material Whenever an author wishes to include a ﬁgure, a table, or a substantial portion of text that has already been published elsewhere (in print or on the Internet), the author must obtain permission from the copyright holder to reproduce the material. It is the author’s responsibility to 1. identify material in a paper or manuscript that has been previously published in print or on the Internet; 2. determine whether that material is subject to copyright protection; 3. if so, identify the copyright owner and request permission in writing; and 4. ensure that permission is granted and forwarded to the author’s publisher. The ﬁrst two points are discussed at the beginning of this chapter. The second two points will be considered next in a general way applicable to requesting permission from any scientiﬁc or scholarly publisher. For information on how to reproduce materials from books, journals, or magazines published by the ACS Publications Division, see Box 7-2. ✐ Reminder: Material published on an Internet site is not necessarily in the public domain, even if the site owner does not have a copyright notice on a Web page. If you download a photograph, illustration, chart, table, or text from a Web site, you must obtain permission from the copyright owner to use it in another publication. Bear in mind that the Web page publisher may not be the copyright owner. Writing To Request Permission Once an author has identiﬁed the tables, ﬁgures, and text that require permission, the next step is for the author to write to the copyright owner to request permission. This is not a difﬁcult task, but it requires some organization and attention to detail, and it may take several months for permission to be granted. Fortunately, the Internet has made the task less burdensome than it used to be because most publishers post their permission policy, forms, and contact information on the Web. Some publishers now have Web-based permission systems. ✐ Reminder: Bear in mind that a copyright owner is not necessarily a publisher. For example, images such as a company logo or a still shot from a movie or television commercial require permission from the corporate ofﬁce or the motion picture studio or the advertising agency. ➤ Begin by organizing your materials requiring permission according to publisher and source. This way, you can list all materials from a single publisher and source on one form, reducing paperwork for yourself and the publisher. 84 ➤ The ACS Style Guide Box 7-2. Permissions at ACS Permission is needed to reproduce tables, ﬁgures, or text from books, journals, or magazines published by the ACS Publications Division. Permission is also needed if adapting or using part of a ﬁgure or table. Permission is not needed if using data from the text to create an original ﬁgure or table. When using a ﬁgure that appeared in an ACS journal and ACS owns copyright to that ﬁgure, permission is not needed to use it in a paper that will appear in the same or another ACS journal, although a credit line is required. The ACS permission policy and forms for ACS journals and magazines are available at http://pubs.acs.org/copyright_info.html and for ACS books, at http://pubs.acs.org/books/forms.shtml. An interactive form can be found at http://pubs.acs.org/cgi-bin/displaycopyright?bichaw. Permission requests to reproduce materials from the books, journals, and magazines of the ACS Publications Division should be directed to the ACS Copyright Ofﬁce. All permission requests must be in writing. The ACS Copyright Ofﬁce accepts permission requests via e-mail, mail, and fax. Permission is granted only by fax or by mail, so it is important to include a fax number. The Copyright Ofﬁce e-mail address is copyright@acs.org. The mailing address is American Chemical Society, Copyright Ofﬁce, 1155 Sixteenth Street, NW, Washington DC 20036. The fax number is 202-776-8112, and the telephone number is 202-872-4368 or 4367. ➤ Determine whether the publisher has permission-request information on the Web and, if so, download or print out the appropriate request forms. (Even if the publisher has a Web-based permission system, you might want to print out the blank form, so you can be sure that you have collected the necessary information when you ﬁll it out online.) ➤ If the publisher does not have forms on the Web, then draft a letter requesting permission. Be sure to include the elements listed in Box 7-3. ➤ List all the material for which you need permission from a given publisher on one form or on the form with an attachment. Unless the publisher speciﬁcally directs differently, avoid submitting one form for each item requiring permission. ➤ Include your speciﬁc deadline date by which you wish to have the permission granted. Chapter 7: Copyright Basics ➤ 85 ➤➤➤➤➤ Box 7-3. Components of a Permission Request Your request for permission to reproduce material will be processed more quickly by a publisher if you provide all the necessary information on the publisher’s form or in a request letter. A permission request should provide the following information: 1. A list of the original ﬁgure or table numbers for each ﬁgure or table that you wish to reproduce from a given source, along with a complete reference citation for the source. • The reference citation for a journal article should include the name(s) of the author(s); the name of the journal; the month, day, and year of publication; volume and issue numbers; and inclusive page numbers for the article. • The reference citation for a book should include the title of the book (and series name and number if applicable); the name(s) of the author(s) or editor(s); the year of publication; and the page numbers on which the original ﬁgures or tables appear. If appropriate, also list the title of the chapter, the name(s) of the chapter author(s), and the inclusive page numbers for that chapter. 2. A description of where the material will be published. Include the title of the forthcoming publication, the type of publication (e.g., journal, book, magazine, or Web journal), and the name of your publisher. 3. A list of the formats in which the requested material will appear, such as print, online, CD-ROM, or proceedings. Unless all rights are requested, only print rights will be granted. 4. Your complete mailing address, e-mail address, and telephone and fax numbers. 5. A speciﬁc deadline (calendar date). Many permission request letters also include a space for the original publisher to specify the publisher’s preferred credit line. ➤ Include complete contact information for yourself, including a mailing address, e-mail address, and telephone and fax numbers. ➤ If you do not have a response from the copyright owner in a reasonable amount of time, contact the publisher again and try to determine the reasons for the delay; perhaps your request was not received or was missing information. Do 86 ➤ The ACS Style Guide not assume that you have permission unless you have heard explicitly from the publisher, even if you set a deadline. What Sort of Credit Line Is Appropriate? ➤ Once the publisher has granted permission to reproduce materials, incor- porate the required copyright credit line into your manuscript. This credit line notiﬁes readers that the publisher owns copyright to the material. Each publisher has its own style for credit lines. For example, the credit line required by the ACS is shown below: Reprinted with permission from REFERENCE CITATION. Copyright YEAR American Chemical Society. (Insert the appropriate information in place of the capitalized words.) ➤ Include the credit line on the ﬁrst page where copyrighted text appears and under each copyrighted table or ﬁgure. ➤ If you are adapting or modifying copyrighted material or if parts of copy- righted material are being used, the words “Adapted” or “Reprinted in part” should replace “Reprinted” in the credit line. Transferring Copyright Most scientiﬁc and scholarly publishers require the transfer of copyright ownership as part of the publication agreement between the publisher and authors. When the publisher owns copyright, it removes the burden from authors to grant permission and it assures them that only legitimate requests for their material are approved. Similarly, if the publisher owns copyright, it is easier for authors who are seeking permission to come to one source that handles requests from multiple references and processes them quickly. If individual authors owned copyright, it might be difﬁcult and cumbersome to contact authors for permission to use their works or portions of their works. If you are in doubt about a publisher’s requirements, contact the publisher or seek legal advice. Each publisher has forms for transferring copyright to the publisher, and the submission of a completed copyright transfer form is nearly always necessary before a publisher will schedule publication of or begin production work on a manuscript. When authors publish in an ACS publication, they assign copyright interest via the ACS Copyright Status Form. This form is available on the ACS Publications Division Web site at http://pubs.acs.org/cgi-bin/displaycopyright?bichaw and in the January issues of ACS journals. Authors publishing books with ACS will ﬁnd a form at http://pubs.acs.org/books/forms.shtml. Completed Copyright Status Forms should be submitted to the appropriate book or journal editor, not the ACS Copyright Ofﬁce. ➤➤➤➤➤ CHAPTER 8 Markup Languages and the Datument Peter Murray-Rust and Henry S. Rzepa A style guide is presumed in its basic objective as guiding authors in the task of producing a document describing their work. In a conventional sense, style is traditionally presentational in objective and is aimed at producing a (visually) homogeneous form suitable for aggregation into a journal issue or a book. At the outset of this chapter, we should pin our ﬂag ﬁrmly to a rather different mast. This chapter is less about the application of style to the presentation of a document and more about the general principles involved in its application to data to achieve a homogeneous form capable of being reused. It is not so much about how to create a document, but rather about how to create a more data-focused entity we call a datument (1), that is, a container for data and its associated descriptions. The datument can have conventional attributes of authorship, afﬁliation, and other familiar structural components, such as sections, tables, ﬁgures, and bibliography, but it extends this by also carrying data. This differs from, for instance, tabulated or quoted data typical of that found in most chemical documents. To illustrate this most important difference, consider the following assertion: The melting point of aspirin is 135°, and its molecular ion has the formula C9H8O4+·. As a human trained in chemistry, you probably understand much of the semantics, but consider how much potential ambiguity and implied meaning is contained in this admittedly concise statement. • You understand what is meant by the term melting point, but you might have to seek a librarian’s help to locate a relevant dictionary of chemical terms where you can check a more precise deﬁnition should the need arise. Copyright 2006 American Chemical Society 87 88 ➤ The ACS Style Guide • After a little thinking, you conclude that the glyph ° indicates that the number preceding it is a temperature expressed in Celsius units. You probably also recognize that this number is probably only accurate to ± 1 °C, only because you have made such measurements yourself. At the back of your mind is probably the knowledge that a value of 135° is reasonable for an organic compound (and that 1135° would not be), that this implies that this substance is a solid at room temperature and that this value may be used as an approximate indicator of chemical purity. • You certainly recognize the term aspirin as a trivial, unsystematic but commonly used description of a nevertheless well-deﬁned molecule (the structure, or more accurately the connection table, of which you may need to ascertain). • The term molecular ion is a term that tends to be used in a particular branch of spectroscopy known as mass spectrometry. • You have little difﬁculty in recognizing the molecular formula as by convention listing the number of carbon atoms as the subscript to the initial C, then followed by the number of hydrogen and then other atoms in alphabetical order. The ﬁnal sufﬁx indicates the charge on the system and reconciles with the use of the term ion, and you will notice that the sufﬁx reveals the presence of an unpaired electron. • You probably are aware of rules that would allow you to check the validity of this formula (i.e., are the + and the • consistent with each other; is the formula physically possible within the constraints of valence theory, etc.). • You might want to derive a molecular mass from the formula, in which case you need to know about atomic weights, isotopes, and other concepts. • You might want to relate the formula to a two-dimensional structural representation, indicating perhaps where the charge might reside, or how the ion might fragment, or a three-dimensional representation for molecular modeling. • As a human, you will infer properties such as aromaticity or the probable presence of a hydrogen bond. A knowledgeable chemist could probably make quite a few more inferences from the above, but the purpose here is to illustrate how much implicit (i.e., undeclared) information there is in such a brief statement (all well-deﬁned chemical terms are shown above in italics to emphasize this). The purpose in writing it all down is to reinforce the idea that although such a statement (as might be found in a document) contains much data, only a human can really make signiﬁcant use of it. Well, that would be true only if the human were to give undivided attention to the contents of such a document; the human certainly could not cope well with more than a few such documents, and not at all with, say, millions of documents. A normal response to such issues of scale would be to say that the essential data and semantics of the above phrase need to be abstracted (with inevitable loss Chapter 8: Markup Languages and the Datument ➤ 89 of some data and information) into a database representation and then suitably queried if needed; after all, agencies such as Chemical Abstracts Service exist to provide such a service. However, consider that the process of converting even a brief statement such as the above into a true chemical abstract requires an expert (and it must be said, error-prone) human. Even then, the knowledge required to construct the list above would have to be acquired from other sources. Could instead much, perhaps all, of this work be handled by a computer? The answer is a clear “yes”, but only if the ground is well prepared for such a task. The purpose of this chapter is to outline some of the basic principles (but not the technical details) of how this could be done and to set out the grander vision that creating an infrastructure that adopts such principles would be the ﬁrst step toward what has been described as a semantic web of information and knowledge. Not only humans but machines could roam, on vast scales if need be, on such a web, and by doing so discover connections between data and concepts which in days past might have been described as the art of scientiﬁc serendipity (2). Markup Languages and the World Wide Web The World Wide Web arose from the need for high-energy physicists at Conseil Européen pour la Recherche Nucléaire (CERN) to communicate and exchange data and information within a large dispersed community. The basic design, which has been well documented, involved the creation of structured documents containing identiﬁable information components linked by uniform resource identiﬁers using markup tags that could be recognized by machines and used as formatting or styling instructions rather than being part of the actual content. Using the HTML version of the previous example:

The melting point of aspirin is 135°, and its molecular ion has the formula C₉H₈O₄^+..

The “tags” in the angle brackets are recognized by the processor as markup and are used as instructions rather than content to produce the previously rendered sentence. Although such examples will be familiar to many readers, we emphasize it here because it illustrates the critical importance of separating content from style (or form). The

tags precisely deﬁne a paragraph, a unit for structuring the document. A machine could now easily count the paragraphs in a document and the number of characters (but not individual words, which are separated not by tags, but by spaces) in each. HTML provides a ﬂexible (perhaps rather too ﬂexible) document structure for text (paragraphs, headers, tables, lists), embedded images (and other multimedia objects), human interactivity (through forms), programs (through scripts, applets, and plug-ins), styling (some degree of formatting and screen layout), and metadata (essentially descriptions of data). 90 ➤ The ACS Style Guide Whereas this is a substantial list, its success has generated many problems, which HTML in its original form cannot solve: • HTML can only support a ﬁxed tagset (for example 59 in the latest speciﬁcation for XHTML 2.0), and even this number is regarded as close to unmanageable (no software yet implements this full set consistently, accurately, and completely). Any other tags that might be present (e.g., ) are simply ignored (strictly speaking, they should be marked as invalid HTML, although they may be valid for other languages). • Much of the behavior (semantics) is undeﬁned. This lack has led to speciﬁc disciplines creating their proprietary methods of supporting functionality (e.g., through scripting languages, plug-ins, applets, and other software). • HTML was designed to be error-tolerant, in recognition that it would be authored (and viewed) mostly by humans. Browsers may try to recover from nonconforming documents and may do so in different ways. Humans are good at recognizing and often correcting errors in HTML (missing links, broken formatting, incomplete text). Machines cannot normally manage broken HTML other than in a “fuzzy” manner. • Author-provided metadata is often entirely absent. If present, it will likely adhere to a general form (the so-called Dublin Core schema, http://dublincore. org/), of limited utility in scientiﬁc, technical, and medical (STM) areas. • The emphasis on presentation in many of the original tags (such as fonts, colors, and layout) muddled the separation of content from style. The World Wide Web Consortium soon developed technologies (CSS, or cascading style sheets, and XSL, or extensible stylesheet language; more information on this and other XML issues is available at http://www.w3c. org/) to help overcome this problem, but as with HTML, CSS is variably implemented in most browsers. Most commercial tools for authoring HTML emphasize presentation or interactivity (to capture the reader’s attention), and in such HTML, the content is subservient to the style. Examples of XML and of Chemical Markup Language These conventional markup approaches (HTML, CSS, and XSL) are inadequate for datuments because there is usually no domain-speciﬁc support. XML, or extensible markup language, was introduced as a solution to this problem. XML was designed to be simple, easy to use, and small; it is a fully conforming subset of the older SGML (essentially “SGML lite”). It allows new markup languages to be deﬁned through an XML schema formalism (see http://www.w3c.org/XML/ Schema). A schema speciﬁes a set of rules (syntax, structure, and vocabulary) to which a document must conform; those that do are said to be “valid”. Schemas allow more precise constraints, allow the deﬁnition of datatypes, and enhance the potential for machine processing. Chapter 8: Markup Languages and the Datument ➤ 91 We start by explaining the terms used in the XML language, illustrated with a small and simple example (kept brief for simplicity and hence not relating to a real molecule) (Scheme 8-1). 150-78-2 1.0/C9H8O4/c1-6(10) 13-8-5-3-2-4-7(8)9(11)12/... Scheme 8-1. The basic features of an XML document. The core of the language consists of a set of data containers, or more formally elements (not to be confused with the chemical elements), the enumeration of which is ideally deﬁned by a schema. In this example, the elements are , , , , , and . These have a clearly deﬁned relationship to one another (illustrated above by indentation of the text). Thus the element is said to be the parent of a child element termed , and both are children of the top-level element , which can also be called the document root element. This hierarchy among elements is precisely deﬁned and must carry no ambiguity. Elements can specify data or information in two ways. First, data can be contained between the start and end of any particular element, such as and in the example. Such content can of course be other (child) elements, but it can also be character or numeric data, as in the example above, which uses both the CAS Registry Number, a unique identiﬁer assigned to chemical structures by CAS (see Appendix 12-3), and a unique canonical molecule identiﬁer known as InChI (International Chemical Identiﬁer) (for more on InChI, see Appendix 8-1). Second, data can also occur as the value of an attribute to the element. In the example above, the element has two attributes, version=“1.0” and convention=“InChI”. Both the name of the attribute and its value can be enumerated if needed by the schema; if the attribute is unknown, or its value is outside deﬁned limits, the entire document or datument can be ﬂagged as invalid by suitable software. Thus has attributes elementType=“C” and x2= “-5.4753”. For the former, a value of “C” is allowed (because it is recognized as the standard symbol for the chemical element carbon), but a value of say “CX” would not be allowed. The second attribute is deﬁned (in the schema) as the x coordinate of a set of two-dimensional molecular coordinates. As such, its presence implies that it should be paired with a y2 coordinate. One can specify in the 92 ➤ The ACS Style Guide schema what kind of behavior to impose if, say, y2 were to be missing. One might decide that its presence would be inferred and that its value should be y2=“0.0”, although in practice that would be a dangerous assumption, and it would be better to ﬂag its absence as an error. Decisions also have to be made regarding the value of this attribute. With two-dimensional coordinates, no assumptions can really be made about the units in which the coordinates are speciﬁed, and it would be up to any software to process the values in a sensible manner. Whereas a human might think that, e.g., x2=“-54753.0” looks unreasonable, it may still be internally consistent with the other coordinates. Such software would probably also be expected to trap conditions such as two atoms with identical coordinates, or truly unreasonable values. However, one can be a little more speciﬁc about, e.g., x3=“-5.4753”. This would be interpreted as the x coordinate of a three-dimensional set, and as such a reasonable implicit behavior would be to treat this value as corresponding to Angstrom units unless otherwise speciﬁed. It is also worth noting that elements which specify data in the form of attributes need not enclose any further data; thus in this case represents both the start and the end of the element (in other words it is an empty container). The preceding discussion has been fairly precise and meticulous, if only to illustrate how XML can be used to impose well-deﬁned structures and relationships on data. We emphasize, however, that it would not normally be a human who has to cope with such levels of detail and precision; the design is such that in fact software will carry almost all of the burden of producing the XML in the ﬁrst place and then validating and using it subsequently. The preceding argument served only to illustrate how such software can be made to safely operate without the need for human intervention in the process. The second example (Scheme 8-2) is an elaboration of the ﬁrst fragment, but formalized below as CML (chemical markup language) (3). We emphasize that this chapter is not meant to be an instructional manual for any given markup language, with CML here serving only to illustrate the general principles involved. Many other scientiﬁc applications of XML have been developed (3, 4), and syntactically, either of these examples could be replaced by other such modularized markup languages. This more extensive example illustrates how a wider range of properties can be deﬁned and also contains a new feature called a namespace. The purpose of this namespace is to enable this entire XML fragment to be combined or aggregated with other XML languages so that no conﬂict between the names used for the elements can arise. This aggregation is achieved by prefacing each element with a unique (to the document) short string: . An attribute xmlns:cml is now used to deﬁne what is called a URI (uniform resource identiﬁer), which stamps a globally unique identiﬁer on the meaning of the cml: preﬁx. This uniqueness will allow this datument to coexist with other XML languages without conﬂict (an example of which is described later in this chapter). Chapter 8: Markup Languages and the Datument ➤ 93 1.0/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h1H3,25H,(H,11,12) 150-78-2 136 Scheme 8-2. A CML datument describing a property of aspirin. The molecule element in this example contains ﬁve child elements: cml:metadata, cml:identifier, cml:atomArray, cml:bondArray, and cml:propertyList. Of these, cml:metadata, cml:atomArray, and cml:bondArray have no children and are empty containers, deﬁning only attribute/value pairs, whereas cml:propertyList has one child, cml:property. The latter itself has a child: cml:scalar. As well as the namespace, the cml:molecule element itself has two other attributes, id and title. The and elements reference namespaces other than CML. This is done to facilitate aggregation with other XML components, such as dictionaries, and by this means to reduce what has been called “tag soup”. For example, deﬁnes a namespace for a dictionary reference called chem:mpt. Any processing software that might need to process a melting point property would be directed to this dictionary for further information on the semantics of this term. Similarly, the 94 ➤ The ACS Style Guide attribute units=“unit:c” would handle the conversion of scientiﬁc units, and dataType=“xsd:decimal” would handle the basic datatype (i.e., the deﬁnition of a decimal number) itself. This mechanism avoids overburdening CML itself with the need to specify such semantics. No other elements or attributes in this example have XML-deﬁned semantics; all other semantics are imposed by CML itself. Thus, the CML schema deﬁnes an enumeration (list) of allowed elementTypes and deﬁnes their meaning, use, and boundaries. These aspects are discussed in more detail below. The Use of Identiﬁers The examples of XML shown in Schemes 8-1 and 8-2 illustrate the use of two types of identiﬁers. The identiﬁer attributes seen in, e.g., are used internally to enable speciﬁcation of, e.g., and should be unique within the datument (but not necessarily globally) to ensure that this XML document is well-formed and valid. The second type is an element containing identiﬁers. Various identiﬁers could be used, such as SMILES, CAS-RN, and the InChI canonical identiﬁer (as shown here), precisely derived from the molecule connection table and used to establish molecular global uniqueness. Any two datuments that contain the same InChI identiﬁer (in this example, C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/ h1H3,2-5H,(H,11,12)) should be presumed to refer to the same molecule (in the sense of a connection table, but not necessarily other properties, such as 3-D coordinates, for example). The whole aspect of identiﬁable data is pivotal to the concepts used here. The CAS-RN is widely used and offers comprehensive coverage from simple molecules to polymers to Markush structures. The InChI can be derived from the structure, but it is still a fairly new standard. It does not yet have wide support and does not yet offer complete coverage of all materials. Display of XML and Speciﬁc XML Languages The default way of “displaying” or “browsing” any XML-compliant language, such as CML, is as a so-called tree view, outlining the structure of the document (Figure 8-1) but to which no style has been applied. Most modern Web browsers will support this feature (we recommend Firefox). Of more utility is to associate a speciﬁc style or transform with this datument. A technology known as XSLT is essentially a speciﬁcation of how an XMLbased datument might be transformed into a different representation (or subset) of the data. Four examples of how this might be used to transform this datument are listed below: • Extraction of atom two- or three-dimensional coordinates and rewrapping with appropriate syntax for interactive display on screen using appropriate Chapter 8: Markup Languages and the Datument ➤ 95 (A) + (B) - + 150-78-2 + (C) - + 1.0/c9h8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h1H3, 2-5H,(H,11,12) 150-78-2 - 136 Figure 8-1. Viewing the XML datument described in Scheme 8-2 in a Web browser, shown as (A) a collapsed tree view, (B) partially expanded, and (C) fully expanded. 96 ➤ The ACS Style Guide software. This use was ﬁrst demonstrated in an unusual series of articles about themselves, in which the theme was to demonstrate how they could be dynamically transformed into other representations of the data contained within (5–7). • Use of the atom array to calculate a molecular formula and weight. • Calculation of molecular properties via invocation of molecular modeling algorithms using, e.g., Web services. • Use as a database query (“Is aspirin in this database?”). Only the ﬁrst of these uses really corresponds to the conventional sense of a document (whether it be an HTML page on the Web or a journal article in PDF format). The last three uses would be true applications of the datument as part of a semantic web. Another difference is that the semantics in such a datument cannot be unambiguously deduced from inspecting such examples but must be formally deﬁned (e.g., in an XML schema or similar tool). Thus, CML2 deﬁnes that, e.g., the atomRef1 and atomRef2 attributes (of the element bondArray) contains references to id attributes on atomArray elements and that the order=“1” attribute relates to a single bond. How a single bond is handled must in turn be speciﬁed by the software; a display program may render the bond in a particular width, color, taper, etc., whereas a database query may handle this information quite differently, or indeed not need it at all. Datument Validation Publishers often provide human-readable guidelines for authors (also known as style guides) for document preparation, which sometimes can extend to entire books. Humans are also quite prone to noncompliance or imperfect compliance because they are often busy or perhaps simply readily bored. Guidelines for data preparation, if they exist, are often to be found in optional categories, such as supporting information. If an author deposits data in such a form, how does the publisher know that it is correct? A key aspect of XML is that documents (and of course datuments) can be validated. For publishing purposes, validation implies a contract between the author and the publisher, which is machine-enforceable. A schema formalizes the syntax, vocabulary, document structure, and some of the semantics. It comprises a set of machine-based rules to which a datument must conform. If it does not, it is the author’s responsibility to edit it until it does. If it conforms, it is assumed that the author has complied with the publisher’s requirements. Validation guarantees that the datument conforms to rules. The more powerful the rules, the more invalid data can be detected. Thus, schemas can allow the detection of some disallowed data, particularly with a controlled vocabulary. An atom in CML is not allowed an elementType of “CO” (arising perhaps as a mis- Chapter 8: Markup Languages and the Datument ➤ 97 print for the element “Co”), or a hydrogenCount of –1. It is, however, allowed a formalCharge of “+10”. This might be corrupted data or a legitimate description of a highly ionized atom. Individual schema-based rules (e.g., for different journals) could allow discrimination between these possibilities. Datument Vocabularies The construction of a schema immediately emphasizes the need for a communal vocabulary. An element such as must be processed in the same consistent manner regardless of the author, the reader, or the processing software. We emphasize “processing”; the implementor must adhere to the same software speciﬁcations, and the software must behave in a predictable manner. For many scientists, this implementation will require a change in their thinking, and we emphasize the consequences here. In its strictest form, this attitude is a controlled vocabulary. Only certain terms may be used, and their meaning is speciﬁed by a trusted authority. An example is IUPAC “gold book” vocabulary of chemical terms and deﬁnitions (at http://www. chemsoc.org/chembytes/goldbook/). Controlled vocabularies are widely used to enforce the mapping of a discipline such as chemistry onto a generally agreed or mandated vocabulary. They often require substantial formal guidelines or training sessions to ensure consistency of interpretation. Markup languages require us to use absolute precision in syntax and structure. It is highly desirable to have additional precision in semantics (the meaning and behavior of documents). The attachment of semantics to documents is not generally appreciated but is a critical process, and we must have a formal means of attaching semantics to every XML element and attribute and their content. At present, this can be achieved in four principal ways, ordered below in terms of machine-understandable rigor. A Human-Readable Prose Description This description can be as simple as a deﬁnition in a dictionary, which may or may not give an indication as to how it might be used. An example from the CIF (crystallographic) dictionary is _chemical_compound_source, which is deﬁned as “description of the source of the compound under study, or of the parent molecule if a simple derivative is studied. This includes the place of discovery for minerals or the actual source of a natural product.” This description formalizes the concept but (deliberately) gives wide latitude in its implementation and content. A Human-Readable Set of Instructions for Machine Implementation Another CIF entry (abbreviated) for _atom_site_U_iso_or_equiv might specify carefully how the concept must be implemented and indicate constraints, such as datatype, enumeration range, and units. The constraints are all machineprocessable, and the deﬁnition includes an implementable algorithmic constraint. 98 ➤ The ACS Style Guide Because CIF predates XML, this deﬁnition is not machine-processable (i.e., it acts as a speciﬁcation for a human programmer, but it cannot be used to generate software automatically). XML schemas provide mechanisms to overcome this. Deﬁnitions by Software Many elements of a controlled vocabulary are effectively deﬁned by software implementation. Thus, the description of the HTML language requires certain elements to have speciﬁed behavior. For example, supports the display of raster images, but the precise look may vary between implementations and ﬁle types. Implementation through software is useful and powerful where authors, publishers, readers, and processors all use the same system. Because STM publishing is increasingly multidisciplinary, this implementation becomes problematic. Often a reader may have to download specialist software that is idiosyncratic and that may not have enough functionality, especially the export of semantically rich data. Moreover, the semantic rules are often buried deep in the software and difﬁcult to understand precisely. Formal Semantics We believe that the chemical community should move toward the adoption of formal rules for expressing semantics and ontology (semantics is the branch of semiotics, the philosophy or study of signs, that deals with meaning. Ontology is deﬁned as a description, such as a formal speciﬁcation of a program, of the concepts and relationships that can exist for an agent or a community of agents). Our central message is that we need carefully constructed and curated machineprocessable ontologies. We believe that scientiﬁc and scholarly organizations have a major role to play and that openness and free access to ontologies is critical. Authoring and Editing Tools At present, most chemical publications are created by authors in a publisher-speciﬁc manner. Each publisher requires a particular document structure, often a particular technology (e.g., formats of text, images, references, and domain-speciﬁc data) and a particular (usually implicit) ontology. The author has to change each of these according to the publisher’s requirements and independently of the content. The publisher (or author) then has to make signiﬁcant technical edits, often as a result of author noncompliance. Original data are transformed into text-oriented formatting languages for rendering to human-readable output, either paper or e-paper, and during this process the machine-processability is lost. Supporting data are often prepared in a variety of (ill-suited) formats; thus, spectral information is frequently merely a scanned image corresponding to the original printed spectrum (itself formatted for human convenience rather than processability). Chapter 8: Markup Languages and the Datument ➤ 99 XML has the potential to revolutionize this situation. With agreed XMLbased markup languages, authors can have a single environment independent of the publishers’ requirements. Publishers can transform the XML into their in-house systems, but quite independently other “reusers” can do so to their own (possibly quite different) requirements. The original datument, which contains all the “supporting data”, can be archived along with the semantics and ontology, all in XML. To achieve all of this consistency, a major change will be required in authoring tools. Instead of proprietary text-based tools, with little useful support for semantics of either text or data, we will require XML-based tools with domain-speciﬁc XML components. An XML editor display environment contains generic mechanisms to manage any domain-speciﬁc schema and therefore ensures that a resulting datument is valid. It will also contain mechanisms for supporting domain-speciﬁc software, such as editors and browsers (e.g., for molecules, spectra, etc.). Much high-quality chemistry software capable of being used in this context is already available. One commercial example based on XML, which encapsulates this concept, has already appeared. The Publicon tool, for example, provides a comprehensive technical authoring environment capable of handling mathematics and expressing the result in XML; interestingly, its target audience includes chemists and bioscientists. Because all XML-conforming markup languages have essentially the same kinds of structures, syntax, and rules, it becomes much easier to write appropriate, often generic, software to handle it. The Datument as a Component of a Scientiﬁc Grid The use of XML has the potential to create savings in certain areas (time for authors and staff costs for technical editors), but a major beneﬁt is that the collected XML datuments, together with the ontologies, would effectively create a machine-processable knowledge base for chemistry. At present, primary publications do not create knowledge without a lot of additional human actions to maximize the knowledge created by primary publications: abstracting, collating, and validating are needed. If this knowledge could be captured and tagged within the primary publication itself, without simply transferring that human action to a different point in the process, a signiﬁcant proportion of the knowledge base could be extracted by machine. If the metadata, structure, datatypes, ontology, semantics, and processing behavior of a piece of information are determined, it essentially becomes a self-describing information component. These information components—which might be implemented by a mixture of XML protocols and object-oriented code—can be regarded as stand-alone, self-describing parts of a knowledge base. Protocols such as XML Query are able to search a heterogeneous aggregate of such components, and RDF (resource description framework, a way 100 ➤ The ACS Style Guide to use metadata so that, for example, search engines can locate it) will be able to make deductions from their metadata. By combination of different markup languages, all information, even at a ﬁne level, can be captured without loss. Any part of it can be retrieved, and hence a collection of marked up XML publications would constitute a knowledge base. If each datument has sufﬁcient high-quality metadata, there may be no essential need for a knowledge base to be centralized. By collecting those publications of interest, any reader or group can create their own personal base. In turn, such metadata can be exported to a wider community using new mechanisms such as RDF or RSS (RDF Site Summary or Rich Site Summary, a way of collecting metadata of interest to an individual reader). With such exciting technologies in the ofﬁng, authors, funders, editors, publishers, and readers have a unique opportunity to start experimenting with creation and dissemination of machine-understandable information and data as an integral part of the process of scientiﬁc publishing. References 1. Murray-Rust, P.; Rzepa, H. S. J. Digital Inf. 2004, 5, article 248, 2004-03-18. 2. Murray-Rust, P.; Rzepa, H. S.; Tyrrell, S. M.; Zhang, Y. Y. Org. Biomol. Chem. 2004, 2, 3192–3203. 3. See Murray-Rust, P.; Rzepa, H. S. J. Chem. Inf. Comput. Sci. 2003, 43, 757–772 and references cited therein. For online information, including schemas, see http://cml.sourceforge. net/. 4. A full review and listing of all scientiﬁcally based XML languages is beyond the scope of this short chapter. Other than CML, the best documented is ThermoML, which is used for thermophysical and thermochemical data. Frenkel, M.; Chirico, R. D.; Diky, V. V.; Marsh, K. N.; Dymond, J. H.; Wakeham, W. A. J. Chem. Eng. Data 2004, 49, 381–393 and references cited therein. 5. Murray-Rust, P.; Rzepa, H. S.; Wright, M.; Zara, S. Chem. Commun. (Cambridge, U.K.) 2000, 1471–1472. 6. Murray-Rust, P.; Rzepa, H. S.; Wright, M. New J. Chem. 2001, 618–634. 7. Gkoutos, G. K.; Murray-Rust, P.; Rzepa, H. S.; Wright, M. J. Chem. Inf. Comput. Sci. 2001, 41, 1124–1130. ➤➤➤➤➤ APPENDIX 8-1 The IUPAC International Chemical Identiﬁer, InChI Stephen R. Heller and Alan D. McNaught The ability to represent uniquely a chemical compound is a fundamental requirement for storage or transmission of chemical information. We deﬁne compounds by their molecular structure, as shown in two-dimensional diagrams or stored in computers. Pronounceable names have been developed for oral and written communication, ranging from the trivial, containing no structural information, to completely systematic names, which can be decoded to yield the original structure. However, the application of systematic nomenclature to complicated structures requires expert knowledge of elaborate systems of nomenclature rules. The use of systematic nomenclature to convey information about the increasingly complex molecular systems handled by today’s chemists is both laborious and inefﬁcient. Over the past decade, with ever-increasing reliance by chemists on computer processing, the International Union of Pure and Applied Chemistry (IUPAC) recognized a need to develop methods of nomenclature that can be interpreted by computers, or more precisely, by computer algorithms. A new program was initiated, aimed at creating a method to generate a freely available, nonproprietary identiﬁer for chemical substances that could be used in printed and electronic data sources. The technical development was carried out primarily at the U.S. National Institute of Standards and Technology, and the product is referred to as the IUPAC International Chemical Identiﬁer (InChI). InChI is not a registry system. It does not depend on the existence of a database of unique substance records to establish the next available sequence number for any new chemical substance being assigned an identiﬁer. Instead, InChI transforms the chemical structure of a compound into a string of characters that uniquely identify that compound. This conversion of a graphical representation of a chemical substance into the unique InChI label can be carried out automatically by any organization, and the facility can be built into any chemical structure drawing program. InChI labels are completely transferable and can be created from existing collections of chemical structures. Whereas the theory needed for conversion of a structure to a unique string of characters has been known for a long time, when work on InChI began there were no freely available unique representations for compound identiﬁcation, nor 101 102 ➤ The ACS Style Guide was their development being actively discussed. Thus, before active development could proceed, a precise speciﬁcation of requirements was wanted, and the following ﬁve characteristics were speciﬁed as needed for such an identiﬁer: 1. The structure of the compound can be drawn using common conventions. 2. The identiﬁer is derived directly from the structure by an algorithm. 3. Exactly one identiﬁer is associated with a given structure, that is, different structures give different identiﬁers. 4. The identiﬁer works for a large fraction of all “drawable” chemical substances. 5. The identiﬁer must be openly available. To be as precise and broadly applicable as desired, InChI uses a layered format to represent all available structural information relevant to compound identity. Each layer in an InChI representation contains a speciﬁc type of structural information. These layers, automatically extracted from the input structure, are designed so that each successive layer adds additional detail. The speciﬁc layers generated depend on the level of structural detail available and whether tautomerism is allowed. Any ambiguities or uncertainties in the original structure will remain in the InChI. The InChI layers are formula (standard Hill sorted); connectivity (no formal bond orders), including disconnected and connected metals; isotopes; stereochemistry, including double bond (Z/E) and tetrahedral (sp3); and tautomers (on or off). Charges are not part of the basic InChI, but rather are added at the end of the InChI string. An example of an InChI representation is given in Figure 8A-1. The acronym InChI and version number are regarded as part of the InChI string (InChI=1 in this case). It is important to recognize, however, that InChI strings are intended for use by computers, and end users need not understand any of their details. In fact, the open nature of InChI and its ﬂexibility of representation, after implementation into software systems, may allow chemists to be even less concerned with the details of structure representation by computers. Source code and an executable version of the structure-to-InChI conversion algorithm are freely available from the IUPAC InChI Web site at http://www.iupac.org/inchi. (A) (B) (C) InChI=1/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)/f/h8,10H,6H2 Figure 8A-1. InChI for guanine: (A) input structure; (B) mobile H canonical numbering, with the attachment points of four mobile H and changeable bonds indicated in bold; and (C) with fixed H canonical numbering. ➤➤➤➤➤ Part 2 Style Guidelines ➤➤➤➤➤ CHAPTER 9 Grammar, Punctuation, and Spelling T his chapter presents grammatical points that cover most situations. It does not attempt to discuss all the rules of grammar; many excellent grammar texts are available for that purpose, such as those given in the selected bibliography, Chapter 18. Writing style and word usage are discussed in Chapter 4. Punctuation, spelling, and word usage are also discussed in Chapter 11 with respect to numbers, mathematics, and units of measure and in Chapter 12 with respect to chemical names. Grammar Subject–Verb Agreement Everyone knows that a subject and its verb must agree in number. Nevertheless, errors in subject–verb agreement are quite common. The primary cause is confusion about the number of the subject. ➤ The number of the subject can be obscured when one or more prepositional phrases come between the subject and the verb. Application of this technique to studies on the phytoplankton biomass and its environments is described. (The subject is “application”, which is singular.) ➤ The number of the subject can be obscured when the sentence is constructed in the order prepositional phrase, verb, subject. To the mixture were added KCl, HEPES, and water. To the solution was added the parent compound. Copyright 2006 American Chemical Society 105 106 ➤ The ACS Style Guide ➤ Two singular subjects joined by “and” require a plural verb. Growth and isolation of M13 virus were described. exception A subject that is plural in form but singular in effect takes a singular verb. Here a compound subject functions as a single entity. Research and development is attracting a growing number of young scientists. Its inventor and chief practitioner is a native son of Boston, Robert Coles. Much inconsistency and confusion exists with technical documentation. ➤ When two or more subjects are joined by “or”, the verb takes the number of the closer or closest subject. All of the pH values or the median pH value was used. The median pH value or all of the pH values were used. ➤ Collective nouns take a singular verb when the group as a whole is meant; in that case, they are often preceded by the word “the”. Collective nouns take a plural verb when individuals of the group are meant; in that case, they are often preceded by the word “a”. contents couple dozen group majority number pair range series variety The number of metal amides synthesized was the largest to date. (Refers to the number as a unit.) A number of metal amides were synthesized. (Refers to each amide.) The series of compounds was prepared to test the hypothesis. (Refers to the series as a unit.) A series of compounds were tested. (Refers to each compound.) The variety of materials tested was sufﬁcient for comparative analysis. (Refers to variety as a unit.) A variety of materials were tested for selective removal of 90Sr from nuclear waste solutions. (Refers to the materials individually.) This group of workers is well aware of its responsibilities. (Refers to the group as a unit.) This group of workers are willing to sign their names. (Refers to the individuals.) ➤ “Data” can be a singular or plural noun. After the data is printed and distributed, we can meet to discuss it. (Refers to the whole collection of data as one unit.) Experimental data that we obtained are compared with previously reported results. (Refers to the data as individual results.) Chapter 9: Grammar, Punctuation, and Spelling ➤ 107 ➤ Units of measure are treated as collective nouns that take a singular verb. The mixture was stirred, and 5 mL of diluent was added. Five grams of NaCl was added to the solution. Three weeks is needed to complete the experiment. To the mixture was added 5 g of compound B. Under high pressure, 5 volumes of solution A was added. ➤ Nouns ending in “ics” and denoting a scientiﬁc discipline are usually singular. dynamics kinetics mathematics mechanics physics thermodynamics Mechanics involves the application of Newton’s three laws of motion. The kinetics of electron transfer to and from photogenerated radicals was examined by laser ﬂash photolysis. The thermodynamics is governed by the positions of the valence and conduction bands. ➤ Compound subjects containing the words “each”, “every”, and “everybody” take singular verbs. Each ﬂask and each holder was sterilized before use. Every rat injected and every rat dosed orally was included. Everybody in the group and every visitor is assigned a different journal each month. ➤ Sometimes, one of these words is implicit; such cases take a singular verb. Each name and address is entered into the database. ➤ If both components of the compound subject do not contain, explicitly or implicitly, one of the words “each”, “every”, or “everybody”, the verb must be plural. Each student and all the professors were invited. ➤ Indeﬁnite pronouns themselves (or adjectives combined with the indeﬁnite pronoun “one”) can be the subject of the sentence. • Those that take a singular verb are “each”, “either”, “neither”, “no one”, “every one”, “anyone”, “someone”, “everyone”, “anybody”, “somebody”, and “everybody”. Each was evaluated for its effect on metabolism. Neither disrupts the cell membrane. 108 ➤ The ACS Style Guide Regarding compounds 1–10, every one reacts with the control agent. Someone measures the volume every day. • Those that take a plural verb are “several”, “few”, “both”, and “many”. Several were evaluated for their effects on metabolism. Few disrupt the cell membrane. Regarding compounds 1 and 2, both react with the control agent. Many were chosen to be part of the study. • Those that take either a singular or a plural verb, depending on context, are “some”, “any”, “none”, “all”, and “most”. The number of the object of the preposition determines the number of the indeﬁnite pronoun related to it. All of the money was stolen. Most of the books were lost. Not all the disks are here; some were lost. ➤ When a fraction is the subject of the sentence, the number of the attendant object of the preposition determines the number of the subject. One-third of the precipitate was dissolved. One-fourth of the electrons were excited. ➤ When a subject and its predicate noun disagree in number, the verb takes the number of the subject. (A predicate noun is the “complement” of a form of the verb “to be”; it refers to the same person or thing as the subject.) The preparation and structure determination [plural subject] of these three compounds are the topic [singular predicate noun] of this paper. The topic of this paper [singular subject] is the preparation and structure determination [plural predicate noun] of these three compounds. Awkward Omissions of Verbs and Auxiliary Verbs ➤ Each subject in a compound sentence must have the proper verb and auxil- iary verb. incorrect The eluant was added to the column, and the samples collected in 10 mL increments. correct The eluant was added to the column, and the samples were collected in 10 mL increments. Chapter 9: Grammar, Punctuation, and Spelling ➤ 109 Restrictive and Nonrestrictive Expressions ➤ A phrase or clause is restrictive when it is necessary to the sense of the sentence; that is, the sentence would become pointless without the phrase or clause. Restrictive clauses are best introduced by “that”, not “which”. It was necessary to ﬁnd a blocking group that would react with the amino group but not with the hydroxyl group. Comparison will be restricted to acetylene compounds that have the same functional end groups. If the clauses beginning with “that” were deleted, the sentences would not convey the information intended. Therefore, the clauses are restrictive. Phrases can also be restrictive. Reactions leading to the desired products are shown in Scheme 1. If the phrase “leading to the desired products” were deleted, the sentence would not convey the information intended. ➤ A phrase or clause is nonrestrictive if it adds information but is not essential; that is, the sentence does not lose its meaning if the phrase or clause is deleted. Nonrestrictive phrases and clauses are set off by commas. Nonrestrictive clauses may be introduced by “who” or “which” but not by “that”. Squalene, a precursor of cholesterol, is a 30-carbon isoprenoid. This highly readable book, written in nontechnical language, surveys the ﬁeld of chemistry by describing the contributions of chemistry to everyday life. Moore, working at the Rockefeller Institute, developed methods for the quantitative determination of amino acids. The current–voltage curves, which are shown in Figure 6, clearly demonstrate the reversibility of all four processes. Several hazardous waste disposal sites are located along the shores of the Niagara River, which is a major water source. Melvin Calvin, who won the Nobel Prize in 1961, elucidated the biochemical pathways in photosynthesis. James Aberdeen, professor emeritus of Central State University, which has provided signiﬁcant scholarship support to minority students over the years, made a generous contribution to the school’s building fund. Dangling Modiﬁers A dangling modiﬁer is a modifying word or phrase that does not clearly and logically modify another word in the sentence. In scientiﬁc writing, the passive voice is often necessary (“the solutions were heated”; “melting points were determined”), but its use can lead to dangling modiﬁers. 110 ➤ The ACS Style Guide ➤ If a modiﬁer precedes the subject of a sentence, it must modify that subject and be separated from it by a comma. Otherwise, it is a dangling modiﬁer. incorrect Splitting the atom, many new elements were discovered by Seaborg. correct Splitting the atom, Seaborg discovered many new elements. incorrect Upon splitting the atom, many new elements were discovered by Seaborg. correct Upon splitting the atom, Seaborg discovered many new elements. incorrect When confronted with these limitations, the experiments were discontinued. correct When confronted with these limitations, we discontinued the experiments. In light of these limitations, the experiments were discontinued. incorrect Understanding the effect of substituents on the parent molecules, the ortho hydrogens could be assigned to the high-frequency peak. correct Understanding the effect of substituents on the parent molecules, we could assign the ortho hydrogens to the high-frequency peak. incorrect Using the procedure described previously, the partition function can be evaluated. correct Using the procedure described previously, we can evaluate the partition function. ➤ In some cases, the passive voice can be used to correct a dangling modiﬁer. incorrect After combining the reactants, the reaction mixture was stirred at room temperature for 3 h. correct After the reactants were combined, the reaction mixture was stirred at room temperature for 3 h. Chapter 9: Grammar, Punctuation, and Spelling ➤ 111 incorrect After stirring the mixture, 5 mg of compound 2 was added. correct After the mixture was stirred, 5 mg of compound 2 was added. ➤ Phrases starting with “based on” must modify a noun or pronoun that usu- ally immediately precedes or follows the phrase. Use phrases starting with “on the basis of ” to modify a verb. incorrect Based on resonance enhancement and frequency shifts, changes in the inter-ring separation were calculated. correct On the basis of resonance enhancement and frequency shifts, changes in the inter-ring separation were calculated. incorrect Based on extensive study, this genetic deﬁciency was attributed to the loss of one isozyme. (“Based on extensive study” modiﬁes the noun “deﬁciency”, but this is not the meaning.) correct On the basis of extensive study, this genetic deﬁciency was attributed to the loss of one isozyme. (“On the basis of extensive study” modiﬁes the verb “was attributed”.) Style guidelines based on authoritative sources are included in this book. (“Based on authoritative sources” modiﬁes the noun “guidelines”.) ➤ “Due to” means “attributable to”; use it only to modify a noun or pronoun directly preceding it in the sentence or following a form of the verb “to be”. incorrect Delays resulted due to equipment failure. correct Delays due to equipment failure resulted. The delays were due to equipment failure. incorrect This high value resulted due to the high conversion efﬁciencies of the enzymatic reactor. 112 ➤ The ACS Style Guide correct This high value is due to the high conversion efﬁciencies of the enzymatic reactor. This high value resulted from the high conversion efﬁciencies of the enzymatic reactor. incorrect Due to exposure to low levels of lead, children can be at risk for developmental problems. correct Because of exposure to low levels of lead, children can be at risk for developmental problems. Children can be at risk for developmental problems because of exposure to low levels of lead. ➤ Absolute constructions are words, phrases, or clauses that are grammatically unconnected with the rest of the sentence in which they appear. They are sometimes called “sentence modiﬁers” because they qualify the rest of the sentence. They may occur anywhere in the sentence, and they are always set off by commas. They are not dangling modiﬁers. Contrary to the excited-state situation, metal–metal bonding interactions in the ground states are weak. The conclusions were premature, considering the lack of available data. Judging from the spectral changes, exhaustive photolysis of compound 4 had occurred. The conformations about the Re–Re bond, in addition, are different for all three complexes. When necessary, the solutions were deaerated by bubbling nitrogen. Clearly, alternative synthetic methods are possible. The instructor having made her point, the discussion continued. Absolute constructions often begin with one of the following words: concerning considering failing given judging provided providing regarding • In mathematical papers, absolute phrases beginning with the words “assuming” and “taking” are often used as sentence modiﬁers. Assuming that distance d is induced by the norm, M is a symmetrical and positively deﬁned matrix. Taking this value as an upper limit, the two shortest distances are sometimes too long for incipient hydrogen bonds. Chapter 9: Grammar, Punctuation, and Spelling ➤ 113 • A subordinate or elliptical clause may be used as a sentence modiﬁer. The compound is stable in air, as we concluded from the experimental evidence. The Mo 5s orbitals, as expected, interact strongly with the ligands. • An introductory inﬁnitive or inﬁnitive phrase may be a sentence modiﬁer. To prepare compound 2, the method of Garner was followed. Reﬂexive Pronouns ➤ Use the reﬂexive pronouns “myself ”, “yourself ”, “himself ”, “herself ”, “itself ”, “ourselves”, and “themselves” only to refer back to a noun or another pronoun in the same sentence. incorrect Please send your manuscript to the associate editor or myself. correct Please send your manuscript to the associate editor or me. The associate editor herself will review your manuscript. incorrect My collaborators and myself will evaluate the results. correct My collaborators and I will evaluate the results. I will evaluate the results myself. I myself will evaluate the results. Punctuation Comma ➤ Use a comma before, but not after, the coordinating conjunctions “and”, “or”, “nor”, “but”, “yet”, “for”, and “so” connecting two or more main clauses (complete thoughts). Toluene and hexane were puriﬁed by standard procedures, and benzene was redistilled from calcium hydride. The role of organic templates in zeolite synthesis has been studied extensively, but no general principles have been delineated. Supported metals are among the most important industrial catalysts, yet only a few have been studied thoroughly. No dielectric constants are available for concentrated acids, so it is difﬁcult to give a quantitative explanation for the results. 114 ➤ The ACS Style Guide ➤ Use a comma after a subordinate clause that precedes the main clause in a complex sentence. Although 40 different P450 enzymes have been identiﬁed, only six are responsible for the processing of carcinogens. Since the institute opened, plant breeders have developed three new prototypes. Because the gene and the molecular marker are so close on the chromosome, they segregate together in the progeny. ➤ Use a comma after most introductory words and phrases. However, the public is being inundated with stories about cancer-causing chemicals. Therefore, the type of organic solvent used is an important factor in lipasecatalyzed enzymatic synthesis. After 3 months, the plants grown under phosphorus-deﬁcient conditions were evaluated. Thus, their motion is the result of the rotation of ferromagnetic domains. On cooling, a crystalline phase may develop in coexistence with an amorphous phase. ➤ Use a comma before the coordinating conjunction in a series of words, phrases, or clauses of equal rank containing three or more items. (This comma is called the serial comma.) Water, sodium hydroxide, and ammonia were the solvents. The red needles were collected, washed with toluene, and dried in a vacuum desiccator. The compound does not add bromine, undergo polymerization by the Diels– Alder reaction, or react with electrophiles. ➤ In compound sentences containing coordinating conjunctions, the clause following the conjunction is punctuated as if it were alone. The reaction proceeds smoothly, and by use of appropriate reagents, the yields will be enhanced. The compounds were separated, and after the ﬁlters had been washed, the experiments were completed. ➤ Do not use a comma to separate a verb from its subject, its object, or its pred- icate noun. incorrect The addition of substituted silanes to carbon–carbon double bonds, has been studied extensively. Chapter 9: Grammar, Punctuation, and Spelling ➤ 115 correct The addition of substituted silanes to carbon–carbon double bonds has been studied extensively. incorrect The disciplines described in the brochure include, materials science, biotechnology, and environmental chemistry. correct The disciplines described in the brochure include materials science, biotechnology, and environmental chemistry. incorrect The solvents used in this study were, cyclohexane, methanol, n-pentane, and toluene. correct The solvents used in this study were cyclohexane, methanol, n-pentane, and toluene. ➤ Do not use a comma before the conjunction joining a compound predicate consisting of only two parts. incorrect The product distribution results were obtained in sodium hydroxide, and are listed in Table 10. correct The product distribution results were obtained in sodium hydroxide and are listed in Table 10. ➤ Use commas to separate items in a series that contains another series in parentheses already separated by commas. The structure was conﬁrmed with spectroscopy (1H NMR, UV, and IR), highresolution mass spectrometry, and elemental analysis. ➤ Use a comma between two or more adjectives preceding a noun only if you can reverse the order of the adjectives without losing meaning. If you can insert the word “and”, the comma is correct. The intense, broad signals of the two groups conﬁrmed their location. The broad, intense signals of the two groups conﬁrmed their location. Sample preparation is a repetitious, labor-intensive task. Sample preparation is a labor-intensive, repetitious task. A powerful, versatile tool for particle sizing is quasi-elastic light scattering. A versatile, powerful tool for particle sizing is quasi-elastic light scattering. 116 ➤ The ACS Style Guide But: Polyethylene is an important industrial polymer. The rapid intramolecular reaction course leads to ring formation. The backbone dihedral angles were characterized by J couplings. The local structural environment of the Mn cluster was determined. ➤ Use a comma before, but not after, the subordinating conjunction in a nonre- strictive clause. incorrect The bryopyran ring system is a unique requirement for anticancer activity whereas, the ester substituents inﬂuence the degree of cytotoxicity. correct The bryopyran ring system is a unique requirement for anticancer activity, whereas the ester substituents inﬂuence the degree of cytotoxicity. ➤ Use commas to set off nonrestrictive phrases or clauses. The products, which were produced at high temperatures, were unstable. ➤ Phrases introduced by “such as” or “including” can be restrictive (and thus not set off by commas) or nonrestrictive (and thus set off by commas). Potassium compounds such as KCl are strong electrolytes; other potassium compounds are weak electrolytes. Previously, we described a mathematical model including a description of chlorophyll degradation in foods. Divalent metal ions, such as magnesium(II) and zinc(II), are located in the catalytic active sites of the enzymes. Hydrogen-bonded complexes, including proton-bound dimers, are well-known species. In the ﬁrst two sentences, the phrases are restrictive because the sentences do not make their points without the phrases. In the third and fourth sentences, the phrases are nonrestrictive because the sentences can make their points without the phrases. ➤ An appositive is a noun that follows another noun and identiﬁes or explains the meaning of the ﬁrst noun. My wife, Jeanne, is a biochemist at the National Institutes of Health. My son James plays baseball, and my son John plays soccer. An appositive is nonrestrictive (and therefore set off by commas) when it names the only possibility. In the ﬁrst sentence, Jeanne is a nonrestrictive appositive. An Chapter 9: Grammar, Punctuation, and Spelling ➤ 117 appositive is restrictive (and therefore not set off by commas) when it points out one of two or more possibilities. In the second sentence, the names of the two sons are restrictive appositives. ➤ Use commas to set off the words “that is”, “namely”, and “for example” when they are followed by a word or list of words and not a clause. Also use a comma after the item or items being named. Use a comma after “i.e.” and “e.g.” in parenthetical expressions. The new derivatives obtained with the simpler procedure, that is, reaction with organocuprates, were evaluated for antitumor activity. Alkali metal derivatives of organic compounds exist as aggregates of ion pairs, namely, dimers, trimers, and tetramers, in solvents of low polarity. Many antibiotics, for example, penicillins, cephalosporins, and vancomycin, interfere with bacterial peptidoglycan construction. These oxides are more stable in organic solvents (e.g., ketones, esters, and ethers) than previously believed. ➤ Use commas to separate two reference citation numbers, but use an en dash (–) to express a range of three or more in sequence, whether they are superscripts or are on the line in parentheses. When they are superscripts, do not use a space after the comma. Experimental investigations10,14,18–25 concerned the relative importance of ﬁeld and electronegativity effects. Certain complexes of cobalt were reported (10, 11) to have catalytic effects on hydrolysis reactions. Flash photolysis studies (3–7) demonstrated the formation of transient intermediate products such as triplet states. ➤ Use a comma before Jr. and Sr., but treat II and III according to the person’s preference. Within a sentence, always use a comma after Jr. and Sr., but use a comma after II and III only if they are preceded by a comma. William M. Delaney, Jr. Charles J. Smith, III John J. Alden II William M. Delaney, Jr., was elected to the governing board. Charles J. Smith, III, received a majority of the votes. John J. Alden II did not run for ofﬁce this year. ➤ Do not use a comma preceding “et al.” unless commas are needed for other reasons. 118 ➤ The ACS Style Guide Saltzman et al. Saltzman, M. J., et al. Saltzman, Brown, et al. ➤ In dates, use a comma after the day, but not after the month when the day is not given. June 15, 1996 June 1996 When giving a complete date within a sentence, use a comma after the year as well. On August 18, 1984, an extraordinary person was born. ➤ When a geographical location is named within a sentence and the name includes a comma, use a comma at the end of the name as well. Iona College, in New Rochelle, New York, is the CEO’s alma mater. The lead researcher, who obtained her education at the University of Calgary, Alberta, Canada, addressed the reporters’ questions. ➤ Use a comma to introduce quotations. In the words of Pasteur, “Chance favors the prepared mind.” Pasteur said, “Chance favors the prepared mind.” ➤ Do not use a comma after a quotation that is the subject of the sentence. “Chance favors the prepared mind” is a translation from the French. (The quotation is the subject of the sentence.) Period ➤ Use a period at the end of a declarative sentence, but never in combination with any other punctuation marks. He said, “Watch out!” She asked, “May I go?” ➤ Do not use periods after most abbreviated units of measure, except when the abbreviation could be confused with a word (in. for inches, at. for atomic, no. for number). ➤ If a sentence ends with an abbreviation that includes a period, do not add another period. She will return at 3 a.m. Chapter 9: Grammar, Punctuation, and Spelling ➤ 119 ➤ Use periods and spaces after initials in persons’ names. J.-L. Gay Lussac J. E. Lennard-Jones M. S. Newman exception Use periods but no spaces when referring to authors of a paper in the acknowledgment paragraph of the paper. R.C.McD. and C.R. thank Dr. Rose Allan for carefully reading the manuscript. C.-C.Y., L.B.-P., N.-h.X., and S.Zh.O. are grateful for generous support from the university. ➤ Do not use periods in abbreviations or acronyms of institution or organization names. ACS CNRS NASA NIH Semicolon ➤ Use a semicolon to separate independent clauses that are not joined by a con- junction. All solvents were distilled from an appropriate drying agent; tetrahydrofuran and diethyl ether were also pretreated with activity I alumina. ➤ Use semicolons between items in a series of words, phrases, or data strings if one or more of the items already contain commas. We thank Zachary Axelrod, University of Michigan, for spectral data; Caroline Fleissner, Harvard University, for helpful discussions; and the National Science Foundation for ﬁnancial support (Grant XYZ 123456). The product was dried under vacuum to give compound 2: yield 68%; IR 1991 m, 1896 s, sh, 1865 s cm–1; 1H NMR 0.36 ppm; 13C NMR 221.3, 8.1 ppm. Figure 1. Cyclic voltammograms in dichloromethane: (a) compound 1, 23 °C; (b) compound 2, –40 °C; (c) compound 4, 23 °C. Figure 6. Ru–H stretches in the IR spectrum of compound 5: ×, 298 K; +, 90 K. This rule holds even if the only group containing the commas is the last in the series. The compounds studied were methyl ethyl ketone; sodium benzoate; and acetic, benzoic, and cinnamic acids. ➤ Use a semicolon between independent clauses joined by conjunctive adverbs or transitional phrases such as “that is”, “however”, “therefore”, “hence”, “indeed”, “accordingly”, “besides”, and “thus”. The rate at which bleaching occurred was dependent on cluster size; that is, the degradation of the mononuclear cluster was about 5 times faster than that of the tetranuclear cluster. 120 ➤ The ACS Style Guide Many kinetic models have been investigated; however, the ﬁrst-order reactions were studied most extensively. The proposed intermediate is not easily accessible; therefore, the ﬁnal product is observed initially. The restriction of the rotational motions of the tert-butyl group gives rise to large entropy changes for the association reaction; hence, the covalent form is relatively easy to identify. The efﬁciency of the cross-coupling depends on the nature of X in RX; thus, the reaction is performed at room temperature by slow addition of the ester. ➤ Do not use a semicolon between dependent and independent clauses. incorrect The activity on bromopyruvate was decreased; whereas, the activity on pyruvate was enhanced. correct The activity on bromopyruvate was decreased, whereas the activity on pyruvate was enhanced. Colon ➤ Use a colon to introduce a word, a phrase, a complete sentence, or several complete sentences that illustrate, clarify, or expand the information that precedes it. Capitalize the ﬁrst word after a colon only if the colon introduces more than one complete sentence, a quotation, or a formal statement. The electron density was studied for the ground state of three groups of molecules: (1) methane–methanol–carbon dioxide, (2) water–hydrogen peroxide, and (3) ferrous oxide–ferric oxide. We now report a preliminary ﬁnding: no chemical shift changes were detected in the concentration range 0.1–10 M. The following are our conclusions: Large-angle X-ray scattering studies give us an accurate picture of structures up to 9 Å. They do not allow the speciﬁcation of defects, such as random ruptures of the chains. The structural models deﬁned are strongly supported by magnetic measurements. ➤ In ﬁgure captions, use a colon to introduce explanations of symbols or other aspects of the ﬁgure. Figure 1. Variable-temperature 1H NMR spectra of compound 12: top, 403 K; middle, 353 K; bottom, 298 K. Figure 3. Brønsted-type plots for aminolysis in 1 M KCl at 25 °C: , 2-nitrophenyl acetate; , 3-chlorobenzoic acid; , 2,6-dinitrobenzoic acid. Chapter 9: Grammar, Punctuation, and Spelling ➤ 121 ➤ Do not use a colon (or any punctuation) between a verb and its object or complement or between a preposition and its object. incorrect The rate constants for the reaction in increasing concentrations of sodium hydroxide are: 3.9, 4.1, 4.4, 4.6, and 4.9. correct The rate constants for the reaction in increasing concentrations of sodium hydroxide are 3.9, 4.1, 4.4, 4.6, and 4.9. incorrect The thermal decomposition was investigated with: gas chromatography, BET surface areas, and X-ray powder diffraction. correct The thermal decomposition was investigated with gas chromatography, BET surface areas, and X-ray powder diffraction. incorrect Transition-metal nitrides have many properties that make them suitable for industrial applications, including: high wear resistance, high decomposition temperature, and high microhardness. correct Transition-metal nitrides have many properties that make them suitable for industrial applications, including high wear resistance, high decomposition temperature, and high microhardness. ➤ Use either a colon or a slash to represent a ratio, but not an en dash. Use either a slash or an en dash between components of a mixture, but not a colon. dissolved in 5:1 glycerin/water dissolved in 5:1 glycerin–water the metal/ligand (1:1) reaction mixture the metal–ligand (1:1) reaction mixture the metal–ligand (1/1) reaction mixture the methane/oxygen/argon (1/50/450) matrix the methane/oxygen/argon (1:50:450) matrix Quotation Marks Location of closing quotation marks with respect to other punctuation is a style point in which ACS differs from other authorities. In 1978, ACS questioned the traditional practice and recommended a deviation: logical placement. Thus, if the punctuation is part of the quotation, then it should be within the quotation 122 ➤ The ACS Style Guide marks; if the punctuation is not part of the quotation, the writer should not mislead the reader by implying that it is. ➤ Place closing quotation marks before all punctuation that is not part of the original quotation. Place them after all punctuation that is part of the quotation. The sample solution was stirred brieﬂy with a magnetic “ﬂea”. Ralph Waldo Emerson said, “The reward of a thing well done is to have done it.” ➤ Use quotation marks around words used in a new sense or words not used literally, but only the ﬁrst time they appear in text. Plastocyanin is a soluble “blue” copper protein. The integrated intensity of each diagonal in the spectrum is proportional to a “mixing coefﬁcient”. The “electron-deﬁcient” cations are, in fact, well-established intermediates. ➤ Use quotation marks to enclose the titles of uniquely named parts and sections of a book or a paper. A complete description of the oils is given in the section “Flavonoids in Citrus Peel Oils”, and other references are listed in the bibliography. But: The preface describes the complexity of the problem. ➤ Use quotation marks to enclose short direct quotations (up to three sentences). In the book Megatrends, Naisbitt concludes, “We are moving from the specialist who is soon obsolete to the generalist who can adapt.” ➤ Use a narrower column width (that is, indented on both sides) for longer quotations (extracts) of 50 words or more. Do not use quotation marks. Everything is made of atoms. That is the key hypothesis. The most important hypothesis in all of biology, for example, is that everything that animals do, atoms do. In other words, there is nothing that living things do that cannot be understood from the point of view that they are made of atoms acting according to the laws of physics. —Richard Phillips Feynman However, this convention does not apply in an article quoting someone who has been interviewed. In such cases, quoted text need not be differentiated by column width, and quotation marks should be used. ➤ Use single quotation marks only when they are within double quotation marks. He said, “You should read the article ‘Fullerenes Gain Nobel Stature’ in the January 6, 1997, issue of Chemical & Engineering News.” Chapter 9: Grammar, Punctuation, and Spelling ➤ 123 Parentheses Parenthetical expressions contain information that is subsidiary to the point of the sentence. The sentence does not depend on the information within the parentheses. ➤ Use parentheses for parenthetical expressions that clarify, identify, or illustrate and that direct the reader. The total amount (10 mg) was recovered by modiﬁcation of the procedure. The ﬁnal step (washing) also was performed under a hood. The curve (Figure 2) obeys the Beer–Lambert law. The results (Table 1) were consistently positive. Only 15 samples (or 20%) were analyzed. ➤ Punctuate after, not before, parenthetical expressions. incorrect Compound 1, (7 mg) obtained by typical workup methods, was used without further puriﬁcation. correct Compound 1 (7 mg), obtained by typical workup methods, was used without further puriﬁcation. ➤ If a parenthetical sentence is within another sentence, do not use a ﬁnal period within the closing parenthesis, and do not start the parenthetical sentence with a capital letter. Our results (the spectra are shown in Figure 5) justiﬁed our conclusions. Our results justiﬁed our conclusions (the spectra are shown in Figure 5). ➤ If a parenthetical sentence is not within another sentence, use a ﬁnal period inside the closing parenthesis, and start the parenthetical sentence with a capital letter. A mechanism involving loss of a CH radical followed by rearrangement was proposed. (The reactions are shown in Scheme 1.) ➤ Use parentheses to enclose numerals in a list. Always use parentheses in pairs, not singly. Three applications of this reaction are possible: (1) isomerization of sterically hindered aryl radicals, (2) enol–keto transformation, and (3) sigmatropic hydrogen shift. 124 ➤ The ACS Style Guide ➤ Use parentheses to identify the manufacturer of reagents and equipment. cobalt chloride (Mallinckrodt) a pH meter with a glass electrode (Corning) ➤ Do not use parentheses when citing a reference number in narrative text. In such a case, the reference number is the point of the sentence, not subsidiary information, and thus not parenthetical. incorrect in ref (12), in (12) correct in ref 12 ➤ Use parentheses in mathematical expressions as discussed in Chapter 11 and in chemical nomenclature and notation as discussed in Chapters 12 and 13. Square Brackets ➤ Use square brackets within quotation marks to indicate material that is not part of a direct quote. In the words of Sir William Lawrence Bragg, “The important thing in science is not so much to obtain new facts as to discover new ways [italics added] of thinking about them.” ➤ Use square brackets to indicate concentration: [Ca+]. ➤ Use square brackets in mathematical expressions as discussed in Chapter 11 and in chemical nomenclature and notation as discussed in Chapters 12 and 13. Dashes The shortest dash is the hyphen (-); the en dash (–) is longer; and the em dash (—) is the longest. Hyphens are discussed in the section on hyphenation in Chapter 10, starting on p 135. En Dash ➤ Use an en dash to mean the equivalent of “and”, “to”, or “versus” in multiword concepts where the words are of equal weight. acid–base titration bromine–oleﬁn complex carbon–oxygen bond cis–trans isomerization cost–beneﬁt analysis dose–response relationship ethanol–ether mixture freeze–pump–thaw degassed helix–coil transition host–guest complexation Chapter 9: Grammar, Punctuation, and Spelling log–normal function metal–ligand complex metal–metal bonding nickel–cadmium battery oxidation–reduction potential producer–user communication pump–probe technique ➤ 125 red–black dichroic crystals structure–activity relationship structure–property relationship temperature–time curve vapor–liquid equilibrium winter–fall maxima 0–t–∞ sequence exception Use a hyphen for color combinations such as blue-green. See Chapter 10, page 140. ➤ Use an en dash to mean “to” or “through” with a span of three or more numerals or other types of ranges. 12–20 months sections 1b–1f Figures 1–4 parts C–E 5–50 kg compounds A–I Lyon and co-workers (23–26) Lyon and co-workers23a–d exception 1 When either one or both numbers are negative or include a symbol that modiﬁes the number, use the word “to” or “through”, not the en dash. –20 to +120 K 10 to >600 mL –145 to –30 °C <5 to 15 mg ≈50 to 60 exception 2 Do not use an en dash when the word “from” or “between” is used. from 500 to 600 mL (not from 500–600 mL) between 7 and 10 days (not between 7–10 days) ➤ Use an en dash to link the names of two or more persons of equal importance used as a modiﬁer. Bednorz–Müller theory Beer–Lambert law Bose–Einstein statistics Debye–Hückel theory Diels–Alder reaction Fermi–Dirac statistics Fischer–Tropsch effect Fisher–Johns hypothesis Flory–Huggins interaction Franck–Condon factor Friedel–Crafts reaction Geiger–Müller effect Henderson–Hasselbalch equation Jahn–Teller effect Lee–Yang–Parr method Lineweaver–Burk method Mark–Houwink plot Meerwein–Ponndorf theory Michaelis–Menten kinetics Stern–Volmer plot van’t Hoff–Le Bel theory Wolff–Kishner theory Young–Laplace equation Ziegler–Natta-type catalyst Treatment of double surnames is covered in Chapter 10 (p 139). 126 ➤ The ACS Style Guide ➤ Use an en dash between components of a mixed solvent. (A slash can also be used.) The melting point was unchanged after four crystallizations from hexane–benzene. Em Dash ➤ Use em dashes to set off words that would be misunderstood without them. incorrect All three experimental parameters, temperature, time, and concentration, were strictly followed. correct All three experimental parameters—temperature, time, and concentration—were strictly followed. ➤ Do not use em dashes to separate phrases or nonrestrictive clauses if another form of punctuation can be used. incorrect Knauth—not Stevens—obtained good correlation of results and calculations. correct Knauth, not Stevens, obtained good correlation of results and calculations. incorrect The singly charged complexes—which constituted bands 1 and 3—liberated maleate anion upon decomposition. correct The singly charged complexes, which constituted bands 1 and 3, liberated maleate anion upon decomposition. Ellipsis Points ➤ Within a quotation, use three periods (points of ellipsis) to indicate deleted words or phrases. These three periods are in addition to other needed punctuation. Thus, if a period is already there, the result will be four periods. No science is immune to the infection of politics and the corruption of power…. The time has come to consider how we might bring about a separation, as complete as possible, between Science and Government in all countries. —Jacob Bronowski ➤ Do not begin or end a quotation with ellipsis points. Chapter 9: Grammar, Punctuation, and Spelling ➤ 127 ➤ Use ellipsis points where part of a series is omitted, when the pattern of the series is unambiguous. a = 1, 2, 3, … n = 2, 4, 6, … x = 1, 3, 5, …, 15 Spelling Consult a dictionary to resolve spelling questions. Merriam-Webster’s Collegiate Dictionary and Webster’s New World College Dictionary are the desk dictionaries used by the ACS technical editing staff. ACS staff members also use the unabridged Webster’s Third New International Dictionary. However, whatever your dictionary, choose the ﬁrst spelling of a word. Use American spellings, except in proper names and direct quotations (including titles). Appendix 9-1 contains a list of the recommended spellings for words that have two or more acceptable spellings. ➤ For the correct spelling and styling of company names, search the Internet for the company and look for the company name on its “contact” page. Do not rely on either a company’s home page or the presence of a particular spelling in a search engine, because the former may be informal and the latter common but also incorrect. Tricky Possessives ➤ Form the possessive of a joint owner by adding an apostrophe and an “s” after the last name only. Celapino and Marshall’s results Bausch and Lomb’s equipment ➤ Form the possessive of plural nouns that do not end in “s” by adding an apos- trophe and an “s”. Form the possessive of plural nouns that end in “s” by adding an apostrophe only. people’s rights children’s books compounds’ structures ➤ Form the possessive of a proper name ending in “s” by adding an apostrophe and an “s”. Jacobs’s laboratory Mathers’s reception 128 ➤ The ACS Style Guide Tricky Plurals Sometimes, the plural form is so familiar that it is used erroneously instead of the singular, usually with Latin and other non-English words. The following list shows the correct singulars and plurals. The preferred forms are given ﬁrst. singular plural alga apparatus appendix bacterium basis criterion erratum focus formula fungus genus helix hypothesis index index latex locus matrix matrix maximum medium minimum phenomenon polyhedron sequela spectrum stratum symposium vertex vortex algae apparatus, apparatuses appendixes, appendices bacteria bases criteria, criterions errata focuses, foci formulas, formulae fungi, funguses genera, genuses helixes, helices hypotheses indexes indices (mathematical) latices, latexes loci matrices (mathematical) matrixes (media) maximums, maxima media, mediums minimums, minima phenomena, phenomenons polyhedrons, polyhedra sequelae spectra, spectrums strata symposia, symposiums vertexes, vertices vortexes, vortices ➤➤➤➤➤ APPENDIX 9-1 Recommended Spelling List Many words in regular usage, as well as many technical terms, have two or more acceptable spellings. The following list gives recommended spellings and capitalizations, where appropriate, for some terms not found in easily accessible dictionaries, words often misspelled, common expressions, and words for which the ACS preference may not match your dictionary’s. absorbance absorbency absorbent accommodate acknowledgment adsorbent aerobic aging aglycon air-dry (verb) ambiguous amine (RNH2) ammine (NH3 complex) amphiphile ampule analog (computer) analogue (structural derivative) analyte analyze annelation annulation antioxidant appendixes aqua regia Arrhenius artifact asymmetry audio frequency autoxidation auxiliary Avogadro bacitracin back-bonding back-donation back-titrate (verb) backscatter backscattering backward band gap bandwidth baseline Beckmann (thermometer, rearrangement) Beer’s law Beilstein bit black box blackbody blender Boltzmann borderline Bragg scattering break-seal break up (verb) breakup (noun) bremsstrahlung bridgehead broad band (noun) broad-band (adjective) Brønsted Büchner build up (verb) buildup (noun) buret butanol, 1-butanol (not n-butanol) 129 130 ➤ The ACS Style Guide n-butyl alcohol tert-butylation byline bypass byproduct byte canceled canister cannot Cartesian catalog chloramine chloro amine chlorophyll a clean up (verb) cleanup (noun) clear-cut close up (verb) close-up (noun) co-ion co-occurrence co-worker coauthor collinear colorimetric complexometric concomitant condensable conductometric conrotatory constantan coordination Coulombic counter electrode counteranion counterion coverslip cross-coupling cross-link cross over (verb) cross-react cross-reaction cross section (noun) cross-sectional (adjective) crossover (noun, adjective) cuboctahedron cut off (verb) cutoff (noun) cuvette cytochrome c Darzens database deamino (not desamino) deoxy (not desoxy) dependent desamine (amino acid names only) desiccator deuterioxide deuteroporphyrin Dewar benzene Dewar ﬂask dialogue diffractometer disc (electrophoresis, compact disc) discernible disk (anatomy, computers) disrotatory dissymmetric distill dry ice drybox dyad e-mail ebullioscopic eigenfunction eigenvalue electroless electron microscope electronvolt electrooptic electropositive eluant eluate eluent Elvehjem end point enzymatic enzymic Erlenmeyer (ﬂask) exchangeable fall off (verb) falloff (noun, adjective) Chapter 9: Grammar, Punctuation, and Spelling far-infrared faradic (referring to current, not the person) fax (noun, verb, adjective) feedback ﬁber-optic (adjective) ﬁber optics (noun) ﬁlterable ﬁrebrick ﬂavin ﬂow sheet ﬂuoborate ﬂuoramine ﬂuoro amine focused follow up (verb) follow-up (noun, adjective) forbear (verb, to refrain) forebear (noun, ancestor) forego (verb, to go before) foreword (part of a book) forgo (verb, to do without) formulas forward (direction) freeze-dry (verb) fulﬁll γ ray gauge Gaussian gegenion glovebag glovebox Gouy graduated cylinder gram Gram-negative Gram-positive gray Grignard groundwater half-ester half-life half-width halfway Hamiltonian Hantzsch ➤ 131 hazmat heat-treat (verb) hemoglobin hemolysate heterogeneous Hoffmann degradation homogeneous homologue Hunsdiecker hydrindan hydriodic hydriodide hydrolysate hydrolyzed ice-cold ice–water bath (use en dash, see p 124) inasmuch indan indexes (book parts, catalog) indices (mathematical) indispensable inﬂection infrared innocuous inoculate insofar inter-ring intra-ring iodometric iodometry isooctane isopiestic isopropyl alcohol (not isopropanol) isosbestic judgment Karl Fischer kayser Kekulé Kjeldahl Kramers Kugelrohr labeled laser leukocyte leveling levorotatory 132 ➤ The ACS Style Guide lifetime ligancy ligate ligated line shape line width liquefy liter lumiﬂavin luster lysate lysed make up (verb) makeup (noun) Markovnikov matrices (mathematical) matrixes (media) megohm Mendeleev mesoporphyrin metalate metalation metallization metallize metalloenzyme meter micro-Kjeldahl mid-infrared midpoint minuscule mixture melting point monochromator Mössbauer naphthyl near-ultraviolet neopentyl Nernstian nuclide occurred occurrence occurring ortho ester orthoformate orthohydrogen orthopositronium outgas outgassing overall parametrization path length percent Petri pharmacopeia phenolphthalein phlorin phosphomonoester phosphorous (as in phosphorous acid) phosphorus (element) phthalic pipet pipetted plaster of Paris point source porphine porphyrin portland cement programmed 2-propanol (not isopropanol) pseudo-ﬁrst-order pyrolysate quantitation radio frequency radioelement radioiodine radionuclide re-form (to form again) reform (to amend) repellent riboﬂavin ring-expand (verb) rotamer scale up (verb) scale-up (noun) scavengeable Schwarzkopf seawater self-consistent selfsame Sephadex set up (verb) setup (noun) side arm (noun) Chapter 9: Grammar, Punctuation, and Spelling side chain sideband siphon Soxhlet spin-label (noun) spin–lattice (use en dash, see p 124) spin–orbit (use en dash, see p 124) steam bath steam-distill (verb) stepwise stereocenter stereopair stereoptically Student’s t test or the Student t test sulfolane sulfur superacid superhigh frequency supernatant (adjective) supernate (noun) syndet synthase synthetase test tube θ solvent thiamin thioacid thioester thioether thioketone toward ➤ 133 transmetalation tropin Ubbelohde ultrahigh vacuum un-ionized uni-univalent upﬁeld urethane van der Waals VandenHeuvel van’t Hoff–Le Bel (use en dash, see p 124) Vigreux vis-à-vis voltameter (measures voltaic electricity) voltammeter (measures ranges of volts and amperes) voltmeter (measures cell potential) wastewater wave function waveform wavelength wavenumber well-known work up (verb) workup (noun) X-irradiation X-ray ylide zerovalent zigzag zinc blende ➤➤➤➤➤ CHAPTER 10 Editorial Style T his chapter presents recommended stylistic and editorial conventions, mainly but not solely for ACS publications. The style recommended by ACS is, for the most part, taken from established authoritative sources, such as The Chicago Manual of Style, Words into Type, and the United States Government Printing Ofﬁce Style Manual. Other points of style are discussed in Chapter 11, “Numbers, Mathematics, and Units of Measure”; Chapter 12, “Names and Numbers for Chemical Compounds”; and Chapter 13, “Conventions in Chemistry”. Hyphenation Consult a dictionary to resolve hyphenation questions. Merriam-Webster’s Collegiate Dictionary and Webster’s New World College Dictionary are the desk dictionaries used by the ACS technical editing staff. ACS staff also use the unabridged Webster’s Third New International Dictionary. Preﬁxes ➤ Most preﬁxes are not hyphenated. Do not hyphenate the following preﬁxes when added to words that are not proper nouns. after ante anti auto bi bio by co counter cyber de di down electro extra Copyright 2006 American Chemical Society hetero homo hyper hypo in 135 136 ➤ The ACS Style Guide infra inter intra intro iso macro mega meso meta metalla metallo micro mid mini mis mono multi nano neo non over peri photo physico poly post pre pro pseudo re retro semi stereo sub super supra techno tele thermo trans tri ultra un under uni up video visco examples antibacterial cooperation cyberspace extranuclear interelectrode isospin microorganism multicolored nonpolar photoredox precooled pseudomorph superacid transactinide viscoelastic exceptions Hyphens are sometimes used (1) when letters are doubled, (2) when more than one preﬁx is present, or (3) when the unhyphenated form does not convey the intended meaning. anti-infective anti-inﬂammatory bi-univalent co-ion co-worker inter-ring intra-ring mid-infrared non-native non-nuclear post-reorganization post-translational pre-equilibrium sub-bandwidth un-ionize ➤ Some preﬁxes may be hyphenated or not, depending on meaning. recollect or re-collect recover or re-cover reform or re-form retreat or re-treat rare exceptions autoxidation counter electrode hetero group homo nucleoside ➤ Do not hyphenate multiplying preﬁxes. hemi, mono, di, tri, tetra, penta, hexa, hepta, octa, ennea, nona, deca, deka, undeca, dodeca, etc. semi, uni, sesqui, bi, ter, quadri, quater, quinque, sexi, septi, octi, novi, deci, etc. bis, tris, tetrakis, pentakis, hexakis, heptakis, octakis, nonakis, decakis, etc. Chapter 10: Editorial Style ➤ 137 examples 2,2′-bipyridine 1,4-bis(3-bromo-1-oxopropyl)piperazine divalent hemihydrate heptacoordinate tetrahedron hexachlorobenzene 1,1′:3′,1″:3″,1′′′-quaterphenyl tetrakis(hydroxymethyl)methane triatomic triethyl phosphate tris(ethylenediamine)cadmium dihydroxide ➤ Hyphenate a preﬁx to a two-word compound. multi-million-dollar lawsuit non-diffusion-controlled system non-English-speaking colleagues non-radiation-caused effects non-tumor-bearing organ pre-steady-state condition pseudo-ﬁrst-order reaction ➤ Hyphenate preﬁxes to chemical terms. non-alkane non-phenyl atoms ➤ Hyphenate a preﬁx to a numeral. pre-1900s ➤ Hyphenate preﬁxes to proper nouns and adjectives, and retain the capital letter. anti-Markovnikov non-Coulombic non-Gaussian non-Newtonian oxy-Cope Sufﬁxes ➤ Most sufﬁxes are not hyphenated. Do not hyphenate the following sufﬁxes when added to words that are not proper nouns. able fold ful less like ment ship wide wise 138 ➤ The ACS Style Guide examples clockwise fellowship lifelike multifold rodlike spoonful statewide worldwide exceptions bell-like gel-like shell-like ➤ Hyphenate the sufﬁxes “like” and “wide” when they are added to words of three or more syllables. bacteria-like computer-like radical-like resonance-like university-wide ➤ Hyphenate the sufﬁx “like” in two-word compounds used as unit modiﬁers. ﬁrst-order-like ion-exchange-like rare-earth-like transition-metal-like ➤ Hyphenate the sufﬁx “like” to chemical names. adamantane-like cycloalkane-like morphine-like oleﬁn-like ➤ Hyphenate a numeral and a sufﬁx. 10-fold 25-fold ➤ Hyphenate sufﬁxes to proper nouns, and retain the capital letter. Asia-wide Claisen-like Kennedy-like Michaelis–Menten-like Compound Words Compound words are two or more terms used to express a single idea. Compound words in common usage are listed in most dictionaries. Many are hyphenated, but many are not. back-reaction cross hairs cross-link crosshatch half-life self-consistent Chapter 10: Editorial Style ➤ 139 ➤ Hyphenate spelled-out fractions. one-half one-ninth three-fourths two-thirds ➤ Hyphenate two-word verbs. air-dry ﬂame-seal freeze-dry jump-start ring-expand vacuum-dry ➤ Do not hyphenate phrasal verbs. As unit modiﬁers or nouns, these words are often hyphenated or closed up; check a dictionary. break down build up grow up hand out line up mix up scale up set off set up slow down stand by take off warm up wear out ➤ Do not hyphenate foreign phrases used as unit modiﬁers. ab initio calculation ad hoc committee in situ evaluation in vivo reactions exception Some foreign phrases are hyphenated in the original language, for example, laissez-faire. ➤ People who have double surnames may choose to hyphenate them or use a space between them. When they are hyphenated, use a hyphen, not an en dash, between the two surnames in a person’s name. Some combinations of two given names are also hyphenated. Robert Baden-Powell David Ben-Gurion Cecil Day-Lewis Chen-Chou Fu Joseph-Louis Gay-Lussac Irene Joliot-Curie Jackie Joyner-Kersee John Edward Lennard-Jones Unit Modiﬁers Unit modiﬁers are two words that together describe a noun; they are almost always hyphenated. Most unit modiﬁers consist of • a noun and an adjective (e.g., time-dependent reaction, radiation-sensitive compound, water-soluble polymer, halogen-free oscillator); • an adjective and a noun (e.g., high-frequency transition, small-volume method, ﬁrst-order reaction, outer-sphere redox couple); 140 ➤ The ACS Style Guide • an adjective and a participle (e.g., slow-growing tree, broad-based support, far-reaching inﬂuence); • a noun and a participle (e.g., time-consuming project, earth-shaking news, silver-coated electrode); • an adverb and an adjective (e.g., above-average results, still-unproven technique); or • two nouns (e.g., ion-exchange resin, liquid-crystal polymers, transitionstate modeling, charge-transfer reaction, gas-phase hydrolysis). The following is a short list (by no means complete) of unit modiﬁers commonly seen in ACS publications. These should be hyphenated when modifying a noun. air-dried air-equilibrated back-bonding 14C-labeled charge-transfer cost-effective diffusion-controlled double-bond electron-diffraction electron-transfer energy-transfer excited-state ﬁrst-order ﬂame-ionization ﬂuorescence-quenching free-energy free-radical gas-phase gel-ﬁltration Gram-negative Gram-positive halogen-free high-energy high-frequency high-performance high-pressure high-resolution high-temperature inner-sphere ion-exchange ion-promoted ion-selective large-volume laser-induced least-squares light-catalyzed long-chain long-lived low-energy low-frequency low-pressure low-resolution low-temperature moisture-sensitive nearest-neighbor oil-soluble outer-sphere radiation-caused radiation-produced radiation-sensitive rate-limiting reversed-phase room-temperature round-bottom rubber-lined second-harmonic second-order short-chain side-chain size-dependent small-volume solid-phase solid-state species-speciﬁc steady-state structure-speciﬁc temperature-dependent thin-layer three-dimensional three-phase time-dependent transition-metal transition-state two-dimensional vapor-phase water-soluble weak-ﬁeld wild-type exceptions particle size distribution water gas shift ➤ Hyphenate combinations of color terms used as unit modiﬁers. blue-green solution bluish-purple solid red-black precipitate silver-gray body Chapter 10: Editorial Style ➤ 141 ➤ Do not hyphenate unit modiﬁers if the ﬁrst word is an adverb ending in “ly”. accurately measured values carefully planned experiment poorly written report recently developed procedure ➤ Hyphenate unit modiﬁers containing the adverbs “well”, “still”, “ever”, “ill”, and “little”. ever-present danger ever-rising costs ill-ﬁtting stopper little-known hypothesis still-new equipment well-known scientist well-trained assistants exception Do not hyphenate unit modiﬁers containing the adverbs “well”, “still”, “ever”, “ill”, and “little” if they are modiﬁed by another adverb. most ill advised investment very high density lipoprotein very well studied hypothesis ➤ Hyphenate unit modiﬁers containing a comparative or superlative if the meaning could be different without the hyphen. best-known processes best-loved advisor higher-temperature values least-squares analysis lowest-frequency wavelengths nearest-neighbor interaction ➤ Do not hyphenate a number and a unit of time or measure used as a unit modiﬁer. 1.2 × 10–4 cm–1 peak 25 K increments 10 mg sample a 0.1 mol dm–3 solution 20 mL aliquot 12˚ angle ➤ When two or more unit modiﬁers with the same ending base modify one noun, use a hyphen after each element, and do not repeat the ending base. ﬁrst- and second-order reactions high-, medium-, and low-frequency measurements ➤ Do not hyphenate unit modiﬁers that are chemical names. acetic anhydride concentration amino acid level barium sulfate precipitate sodium hydroxide solution 142 ➤ The ACS Style Guide ➤ Hyphenate unit modiﬁers made up of a single letter or number and a noun or adjective. α-helix structure 13C-enriched proteins 14C-labeling patterns d-conﬁguration settings γ-ray spectrometer 1-isomer proﬁle O-ring suppliers π-electron system 3-position substitution s-orbital diagrams t-test analysis U-band transmitter x-axis labels X-band radar ➤ Do not hyphenate unit modiﬁers if one of the words is a proper name. Fourier transform technique Lewis acid catalysis Schiff base measurement ➤ Hyphenate unit modiﬁers that contain spelled-out numbers. ﬁve-coordinate complex one-electron transfer seven-membered ring three-dimensional model three-neck ﬂask three-stage sampler two-compartment model two-phase system ➤ Hyphenate unit modiﬁers that contain a present or past participle. air-equilibrated samples English-speaking colleagues ﬂuorescence-quenching solution hydrogen-bonding group immobilized-phase method ion-promoted reaction laser-induced species methyl-substituted intermediate photon-induced conversion rate-limiting step research-related discussion steam-distilled sample caution Watch for cases where the participle forms a unit with the noun that follows: for example, “ligand binding site” should not be hyphenated. ➤ Hyphenate unit modiﬁers of three or more words. head-to-head placement high-molecular-weight compound nine-membered-ring species out-of-plane distance root-mean-square analysis signal-to-noise ratio tried-and-true approach voltage-to-frequency converter ➤ Hyphenate unit modiﬁers containing three words when similar two-word modiﬁers are hyphenated. acid-catalyzed reaction general-acid-catalyzed reaction metal-promoted reaction transition-metal-promoted reaction Chapter 10: Editorial Style ➤ 143 exception Do not hyphenate unit modiﬁers containing three or more words, even if similar two-word modiﬁers are hyphenated, when doing so would break other rules. For example, do not hyphenate unit modiﬁers if one of the words is a proper name. Do not hyphenate unit modiﬁers that are twoword chemical names. acid-catalyzed reactions (but Lewis acid catalyzed reactions) copper-to-iron ratio (but sodium chloride to iron ratio) ➤ Hyphenate unit modiﬁers used as predicate adjectives. (Predicate adjectives are usually used with the verb “to be”; they are adjectives that modify the subject but come after the verb.) Usually, only unit modiﬁers that consist of nouns and adjectives or nouns and participles can be used as predicate adjectives. All compounds were light-sensitive and were stored in the dark. In these cluster reactions, dehydrogenation is size-dependent. The antibody is species-speciﬁc. The complex is square-planar. The movie was thought-provoking. The reaction is ﬁrst-order. ➤ Hyphenate phrases also containing en dashes (see pp 124–126) when they are used as unit modiﬁers. alkyl–heavy-metal complexes high-spin–low-spin transition metal–metal-bonded complexes Michaelis–Menten-like kinetics retro-Diels–Alder reaction transition-metal–chalcogen complexes ➤ Hyphenate phrases containing parenthetical expressions when they are used as unit modiﬁers. element (silicon or tin)-centered radicals Capitalization In Text Generally, in text keep all words lowercase, including chemical names and terms, except proper nouns and adjectives. However, there are many exceptions. ➤ Capitalize the words “ﬁgure”, “table”, “chart”, and “scheme” only when they refer to a speciﬁc numbered item. Chart 4 Figure 1 Schemes 4–7 Table II 144 ➤ The ACS Style Guide ➤ Do not capitalize the “r” in “X-ray” at the beginning of a sentence or in a title. ➤ Capitalize parts of a book when they refer to a speciﬁc titled and numbered part. Appendix I Chapter 3 Section 4.2 But the appendix the chapter the contents the preface ➤ Capitalize only the name of an eponym, not the accompanying noun. Lewis acid nuclear Overhauser effects Raman spectroscopy Schiff base Avogadro’s number Boltzmann constant Einstein’s theory Graham’s law Hodgkin’s disease exceptions Nobel Peace Prize Nobel Prize ➤ Capitalize adjectives formed from proper names. Boolean Cartesian Copernican Coulombic Darwinian Einsteinian Freudian Gaussian Hamiltonian Laplacian Lorentzian Mendelian Newtonian ➤ Capitalize the ﬁrst word after a colon if the colon introduces more than one complete sentence, a quotation, or a formal statement. Chemists ﬁnd enzymes attractive as potentially useful synthetic tools for many reasons: Enzymes catalyze reactions with high regio- and stereoselectivity. They cause tremendous rate accelerations under mild reaction conditions. They reduce the need for protecting groups and give enantiomerically pure products. An emulsion is a thermodynamically unstable system: it has a tendency to separate into two phases. Two types of asymmetric reactions were conducted: synthesis of styrene oxide and reduction of oleﬁnic ketones. The editor wishes to make the following point: No papers will receive preferential treatment on the basis of artwork. Chapter 10: Editorial Style ➤ 145 ➤ Do not capitalize lowercase chemical descriptors hyphenated to chemical names when they are at the beginning of a sentence. cis-4-Chloro-3-buten-2-one was obtained in 74% yield. o-Dichlorobenzene was the solvent. ➤ When the ﬁrst word of a sentence is a roman chemical descriptor that is not part of a chemical name, capitalize it. Cis and trans isomers are used in pharmaceuticals and agrochemicals. Erythro diols were obtained in good yield. Syn hydroxylation of cycloalkenes was attempted. Trans hydroxyl groups are oxidized biochemically. ➤ Do not capitalize chemical names or nonproprietary drug names unless they are at the beginning of a sentence or are in a title or heading. In such cases, capitalize the ﬁrst letter of the English word, not the locant, stereoisomer descriptor, or positional preﬁx. (See Chapter 12, “Names and Numbers for Chemical Compounds”.) ➤ Some reaction names are preceded by element symbols; they may be used as nouns or adjectives. When they are the ﬁrst word of a sentence or appear in titles and headings, the ﬁrst letter of the word is capitalized. N-Oxidation of the starting compounds yielded compounds 3–10. N-Benzoylated amines undergo hydroxylation when incubated with yeast. Preparation of S-Methylated Derivatives O-Substituted Structural and Functional Analogues ➤ When a sentence begins with a symbol that is not hyphenated to the following word, the word is not capitalized. π-Electron contributions are evident. π electrons make signiﬁcant contributions in this system. σ values were calculated from eq 3. ➤ Always capitalize kingdom, phylum, class, order, family, and genus taxonomic names, as well as names of cultivars. Subclassiﬁcations follow the same presentation as the main category. Animalia, Planta (kingdom) Chordata (phylum) Vertebrata (subphylum) Mammalia, Reptilia (class) Primates, Testudines (order) 146 ➤ The ACS Style Guide Hominidae, Apiaceae (family) Homo, Drosophila (genus) Lycopersicon esculentum Mill. cv. Jennita (cultivar) ➤ Use lowercase for species, subspecies, and varieties, even in titles. Escherichia coli Achromobacter haemolyticus subsp. alcaligenes Zea mays var. rugosa (variety) Three New Dihydroisocoumarins from the Greek Endemic Species Scorzonera cretica ➤ Do not capitalize the abbreviation for species, singular or plural (sp. or spp., respectively), subspecies (subsp.), variety (var.), or cultivar (cv.). Salmonella sp. Polygonum spp. Petroselinum crispum Mill. subsp. tuberosum Zea mays var. rugosa Lycopersicon esculentum Mill. cv. Jennita ➤ Do not capitalize genus names used as common nouns except at the begin- ning of a sentence or in a title or heading. bacillus gorilla, a member of the genus Gorilla hippopotamus, a member of the genus Hippopotamus klebsiella pseudomonad, a member of the genus Pseudomonas streptococcus ➤ Do not capitalize the adjectival or plural form of a genus name unless it is at the beginning of a sentence or in a title or heading. bacilli pneumococcal streptococcal ➤ In text, do not capitalize polymer names that contain the names of the polymerizing species in parentheses following the preﬁx “poly”. At the beginning of a sentence, capitalize only the “P” in “poly”. Poly(vinyl chloride) is a less useful polymer than poly(ethylene glycol). ➤ Capitalize trademarks; use them as adjectives with the appropriate nouns. Ficoll Novocain (but novocaine) Plexiglas (but plexiglass) Pyrex Sephadex Styrofoam Teﬂon Triton Tween Chapter 10: Editorial Style ➤ 147 ➤ Do not capitalize the word “model” with a number or code. γ counter (Beckman model 5500B) mass spectrometer (PerkinElmer model 240C) multichannel spectrometer (Otsuka model MCPD-1000) spectrometer (Varian model XL-200) Waters model 660 gradient controller ➤ Do not capitalize the common names of equipment. dynamic mechanical analyzer electron-diffraction chamber ﬂame-ionization detector gas chromatograph mass spectrometer mercury lamp spectrophotometer temperature controller unit ➤ Use only an initial capital letter, not all capitals, for company names that are not acronyms, because company names are not trademarks and are not protected by law. Valspar Corporation Xerox Corporation But EMD Chemicals Inc. IBM Corporation ➤ Capitalize the names of speciﬁc organizations or entities, including ACS local sections, committees, and governing bodies, but not the general terms for them. ACS Board of Directors ACS Committee on Analytical Reagents ACS Division of Fuel Chemistry American Chemical Society Clean Water Act Environmental Protection Agency the Milwaukee Section University of Michigan the board an ACS committee the division the society the act the agency a local section the university ➤ Capitalize the names of speciﬁc titles when they appear with a person’s name, but not the general terms for them. the professor the general the mayor Professor Perry Key General James Shore Mayor Ralph Estes Walter Baldwin, Professor of Chemistry 148 ➤ The ACS Style Guide The well-known professor Perry Key will give a tutorial. James Shore, a general in the U.S. Army, will teach a graduate course. Our speaker will be the retired general James Shore. Isaac Bickford is an assistant professor. Ralph Estes is the mayor of a small town in upstate New York. ➤ Capitalize the names of special events but not the general terms for them. 229th ACS National Meeting 39th ACS Western Regional Meeting 79th ACS Colloid and Surface Science Symposium the regional meeting the spring national meeting the symposium ➤ Capitalize sections of the country but not the corresponding adjectives. the Midwest, but midwestern the Northeast, but northeastern ➤ Do not capitalize the names of the four seasons: summer, fall, autumn, win- ter, spring. ➤ Capitalize Earth, Sun, and Moon only when used in an astronomical sense. Venus and Mars are the closest planets to Earth. The Earth rotates on its axis and revolves around the Sun. The Moon is the only body that orbits the Earth. But Water bodies on the earth’s surface contain a variety of chromophoric substances. Pollution occurs to some extent everywhere on earth. The sun is the primary source of radiation that can cause chemical transformations. The next full moon will be on Thursday. In Titles and Headings These guidelines apply to titles and headings at all levels; that is, they apply to subtitles and subheadings. They also apply to table, scheme, and chart titles. ➤ In titles and headings that are typeset in capital and lowercase letters, capital- ize the main words, which are nouns, pronouns, verbs, adjectives, adverbs, and Chapter 10: Editorial Style ➤ 149 subordinating conjunctions, regardless of the number of letters. Do not capitalize coordinating conjunctions (“and”, “but”, “or”, “nor”, “yet”, “so”), articles (“a”, “an”, “the”), or prepositions. Do capitalize the “to” in inﬁnitives. Do capitalize the ﬁrst and last words of a title or heading, regardless of part of speech, unless the word is mandated to be lowercase (e.g., pH, d Orbital). Changes in the Electronic Properties of a Molecule When It Is Wired into a Circuit Derivatives from a Chiral Borane–Amine Adduct In Situ Nutrient Analyzer In Vitro and in Vivo Antiestrogenic Effects of Polycyclic Musks in Zebraﬁsh Nickel-Catalyzed Addition of Grignard Reagents: Ring-Opening Reactions with Nucleophiles Phosphonolipids with and without Puriﬁed Hydrophobic Lung Surfactant Proteins Properties of Organometallic Fragments in the Gas Phase Reactions of Catalyst Precursors with Hydrogen and Deuterium Scope of the Investigations: The First Phase The Computer as a Tool To Improve Chemistry Teaching Vibrations in Situ exception 1 In titles and headings, capitalize small words that are parts of phrasal verbs. Break Down Build Up Set Off Set Up Slow Down Wear Out exception 2 In titles and headings, capitalize small words that are parts of phrasal adjectives. End-On Bonding In-Plane Atoms Side-On Bonding (but Out-of-Plane Vibrations [only the ﬁrst preposition is capitalized]) ➤ In titles and headings, capitalize “as” when it is used as a subordinating con- junction but not when it is used as a preposition. Alumina as a Catalyst Support Kinetics of Cyanocobalamin As Determined by Binding Capacity ➤ Do not capitalize the “r” in “X-ray” in titles and headings. Do capitalize the “r” in “γ ray” and the “p” in “α particle” and “β particle” in titles and headings. 150 ➤ The ACS Style Guide ➤ Do not capitalize lowercase chemical descriptors in titles and headings, but do capitalize the ﬁrst letter of the English word. Reaction of trans-4-(Phenylsulfonyl)-3-buten-2-one ➤ When abbreviated units are acceptable in titles and headings, do not cap- italize those that are ordinarily lowercase. Analysis of Milligram Amounts Determination of N-Nitrosodimethylamine at Concentrations <7 ng/L ➤ Always capitalize genus names, but never capitalize species names, in titles and headings. Active-Site Nucleophile of Bacillus circulans Xylanase Novel Metabolites of Siphonaria pectinata ➤ In titles and headings, capitalize all main words in a unit modiﬁer. Base-Catalyzed Cyclization Cross-Linked Polymer Deuterium-Labeling Experiment High-Temperature System Non-Hydrogen-Bonding Molecules Thyrotropin-Releasing Hormone ➤ In titles and headings, capitalize each component of compound words if the component would be capitalized when standing alone. Cross-Link Half-Life Quasi-Elastic ➤ Do not capitalize hyphenated sufﬁxes. Synthesis of Cubane-like Clusters ➤ In titles and headings, capitalize only the ﬁrst letter (“P”) of polymer names that contain the names of the polymerizing species in parentheses following the preﬁx “poly”. IR Spectroscopic Analysis of Poly(1H,1H-ﬂuoroalkyl α-ﬂuoroacrylate) Light-Scattering Studies of Poly(ethylene-co-butylene) New Uses for Poly(ethylene terephthalate) Polystyrene-block-poly(2-cinnamoylethyl methacrylate) Adsorption Reactions of Poly(methyl methacrylate) Synthesis and Characterization of Poly(isobutylene-b-methyl vinyl ether) Chapter 10: Editorial Style ➤ 151 ➤ Capitalize only the ﬁrst letter in a chemical name containing complex substituents in parentheses or brackets. 2-[3-[2-[(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethylamino]-3-methyl-1-oxobutyl]1,2,3,4-tetrahydroisoquinoline: A Potent, Selective, and Orally Bioavailable Dipeptide-Derived Inhibitor of Dipeptidyl Peptidase IV Preparations of (Methyl isocyanide)iron Compounds Structures of Tetrakis(methyl isocyanide)iron Complexes ➤ Capitalize parenthetical phrases in titles and headings as if they were not par- enthetical. Versatile Organic (Fullerene)–Inorganic (CdTe Nanoparticle) Nanoensembles Surnames Capitalization Although a current trend is to lowercase the surnames of persons when these names are used as modiﬁers and have become very familiar, many are still capitalized. The following is a list (by no means complete) of names that should be capitalized. Avogadro Beckmann Beilstein Boltzmann Bragg Brønsted Büchner Bunsen Claisen Dewar benzene, ﬂask Dreiding Erlenmeyer Gram Kekulé Kjeldahl Mahalanobis Markovnikov Mössbauer Petri Poiseuille Poisson Priestley Scatchard VandenHeuvel exceptions de Broglie van der Waals van’t Hoff ➤ Surnames that are used as units of measure are lowercase. ampere angstrom coulomb curie dalton darcy debye einstein faraday gauss gilbert gray hartree henry hertz joule kelvin langmuir newton ohm pascal poise siemens sievert stokes tesla watt weber 152 ➤ The ACS Style Guide In the temperature–current curves, temperature is given in kelvins and current is shown in amperes. NMR coupling constants are reported in hertz. Hyphenation ➤ Hyphenation of double surnames is discussed on p 139. ➤ Hyphenate preﬁxes and sufﬁxes to proper names as nouns and adjectives, and retain the capital letter. anti-Markovnikov hetero-Diels–Alder Kennedy-like Michaelis–Menten-like non-Coulombic non-Gaussian non-Newtonian oxy-Cope retro-Diels–Alder Foreign Surnames Some foreign surnames follow a format different from the American system. The Chinese use their surnames ﬁrst, followed by their given names. For example, Sun Yat-sen’s surname is Sun. However, the problem of identifying surnames extends to many other cultures. This multiplicity of usage can create problems in bibliographic indexes and in reference citations. A reference citation in a bibliography should always list the surname ﬁrst, followed by given name or initials. In a byline, the author names should be presented in standard American format (given names ﬁrst and surnames last) to ensure consistency of citation practice. If a footnote would clarify the situation or eliminate any perceived confusion, use a footnote. In most cultures, the surname is the family name, but it may not be the formal name, that is, the name or shortest string of names that are properly used following a title (Mr., Dr., Professor, etc.). Presented here are some cases in which different customs are used for the order of surnames, given names, and formal names. This list is by no means complete, but at least it will help you to be aware of these differences. arabic Often many names; the position of the surname is highly variable. The formal name often consists of two or three names, including articles that can be joined. Examples: Ibn Saud, Abd al-Qadir. chinese Two or three names; the surname is ﬁrst. Examples: Chiang Kaishek is Dr. Chiang; Chou En-lai is Dr. Chou. hebrew Two or three names; the surname is the last one or two and is the formal name. Examples: David Ben-Gurion is Dr. Ben-Gurion; Moshe BarEven is Dr. Bar-Even. Chapter 10: Editorial Style ➤ 153 hungarian Two names; the surname is ﬁrst, and it is the formal name. However, the second name is accepted as formal internationally. japanese Two names; the surname is the formal name. The surname is ﬁrst in Japanese. However, when the names are translated into non-Asian languages, surnames appear last. Example: Taro Yamada is Dr. Yamada. korean Usually three names; the surname is ﬁrst and is the formal name. In North Korean names, all three parts start with a capital letter. Examples: Kim Il Sung is Dr. Kim. In South Korean names, the two parts of the given name are hyphenated, and the second part is lowercase. Example: Kim Young-sum is Dr. Kim. spanish Frequently three or more names; the last two are surnames, sometimes connected by “y”. The second surname is often dropped or abbreviated. The formal name begins with the ﬁrst surname and includes the second surname only in very formal usage. Example: Juan Perez Avelar is Dr. Perez or Dr. Perez Avelar, but never Dr. Avelar. The two surnames may also be hyphenated. Example: José Gregorio Angulo-Vivas is Dr. Angulo or Dr. Angulo-Vivas, but never Dr. Vivas. thai Two names; the surname is last, but the formal name is ﬁrst. vietnamese Two or three names; the ﬁrst is the surname and formal name. initials Some foreign names are abbreviated with two-letter initials that reﬂect transliteration from a non-Latin alphabet: Ch., Kh., Ph., Sh., Th., Ts., Ya., Ye., Yu., and Zh. Some foreign names are abbreviated with hyphenated initials: C.-C. Yu. Special Typefaces Special typefaces help the reader quickly distinguish certain letters, words, or phrases from the rest of the text. Italic Type Chapter 11 describes the use of italic type in mathematical material, and Chapters 12 and 13 give guidelines for the use of italic type in chemical names and conventions in chemistry. ➤ Use italic type sparingly to emphasize a word or phrase. Do not use italics for long passages. 154 ➤ The ACS Style Guide ➤ Use italic type for a word being deﬁned or for a newly introduced term the ﬁrst time it appears in text. In an outer-sphere transfer, an electron moves from reductant to oxidant with no chemical alteration of the primary coordination spheres. We call these materials microcapsules. ➤ Use italic type for the titles and abbreviations of periodicals, books, and newspapers. If “the” is the ﬁrst word of the title, italicize and capitalize it. An article on a promising cholesterol biosynthesis inhibitor appeared in The Journal of Organic Chemistry this month. Enough for One Lifetime is the biography of Wallace Carothers. I read three articles on that new chiral compound in the Journal of the American Chemical Society. The Washington Post did a feature story on the president’s daughter. ➤ Do not use italic type for common Latin terms and abbreviations. a priori ab initio ad hoc ca. de novo e.g. et al. etc. i.e. in situ in vitro in vivo status quo vs ➤ Use italic type for genus, species, subspecies, and variety names of all animals, plants, and microorganisms, but not when these names are used as singular or plural common nouns or when they are adjectival. a bacterium of the genus Salmonella Bacillus coagulans and Bacillus dysenteriae are two species of bacilli. Staphylococcus aureus is the bacterium that causes staphylococcal infection. Streptococcus pneumoniae (genus and species) The red rhododendron, Rhododendron arboreum, needs bright sun. Achromobacter haemolyticus subsp. alcaligenes (subspecies) Zea mays var. rugosa (variety) ➤ Use italic type for genotypes (representations of genes) and roman type for phenotypes (representations of proteins). The vanA gene that encodes one such inducible resistance protein is designated VanA. E. coli DH5α ∆(lacZYA–argF)U169 deoR recA1 endA1 hsdR17(rK+, mK+) supE44 λ– thi-1 gyrA96 relA1 F′ proAB+ lac1qZ ∆ M15 ssf::Tn5 [Kmr] Chapter 10: Editorial Style ➤ 155 ➤ Names of restriction endonucleases should follow the typeface conventions of the names from which they were derived: use italic type for the three-letter portion derived from the genus and species name; use roman type for additional strain designators (letters and/or arabic numerals) and for the roman numeral identiﬁers. BamHI EcoRI HaeII HaeIII HindIII Sau3AI SmaI XhoI exception Use roman type for abbreviations of general enzyme types. Exo III for exonuclease III Pol α for DNA polymerase α Topo II for topoisomerase II ➤ Do not use italic type for “pH”; “p” is always lowercase, and “H” is always capitalized. ➤ Do not use italic type for M (molar) or N (normal). Do use italic type for m (molal). Greek Letters ➤ Use Greek letters, not the spelled-out words, for chemical and physical terms. Do not italicize Greek letters. α helix (not alpha helix) β particle (not beta particle) β sheet (not beta sheet) γ radiation (not gamma radiation) NFκB (nuclear factor κB) (not NF kappa B) exceptions delta opioid receptor mu opioid receptor Computer-Related Usage ➤ Capitalize the ﬁrst letter of the names of computer languages. AP Basic Cobol Eiffel Fortran Java Logo Pascal Perl Python Smalltalk 156 ➤ The ACS Style Guide ➤ Capitalize the ﬁrst letter of the names of programs, and follow the man- ufacturer’s or creator’s usage within the name. Acrobat Alchemy ChemDraw ChemIntosh ChemPlus EasyPlot EndNote FileMaker Pro Freehand HyperChem ISIS/Draw KaleidaGraph LaTeX Mathematica MathType Microsoft Excel Microsoft PowerPoint Microsoft Word Molecular Presentation Graphics MULTAN78 Oracle Photoshop ProCite SigmaPlot SIMI4A Symphony TK Solver Un-Plot-It UniVersions WordPerfect ➤ Use lowercase letters for the spelled-out forms of protocols, except as the ﬁrst word of a sentence and in titles and headings. network news-transfer protocol (NNTP) Appendix 10-1 contains a list of some common computer and Internet terms. Uniform Resource Locators A typical uniform resource locator (URL), which is an address on the World Wide Web, takes the following forms: http://www.domain.zone http://www.domain.zone/name1/~name2/ http://domain.zone/name1/~name2/name3.html The number of names varies. For example, http://www.chemistry.org http://nobelprize.org/chemistry/index.html These examples are short, but URLs can be quite long, and in narrative text they often will need to be broken at the end of a line. If the URL does not fit on one line, it can be broken according to the following guidelines: ➤ Break after an ampersand, a slash, or a period, but keep two slashes together. ➤ Do not add a hyphen to the end of the line. ➤ Do not break after a hyphen to avoid confusion as to the hyphen’s purpose. Chapter 10: Editorial Style ➤ 157 E-Mail Addresses A typical e-mail address usually takes one of these forms: personname@companyname.zone initial_surname@companyname.zone surnameinitial@companyname.zone All kinds of variations on the person’s name and initials are possible, and besides the underscore, other types of punctuation are used. Long names are often truncated. ➤ Break e-mail addresses in text after the @ or a period. Do not insert a hyphen or any other character. Chapter 14, “References”, presents the editorial style for electronic sources listed in reference lists and bibliographies. Trademarks A trademark is an adjective that describes a material or product (e.g., Teﬂon resin, Kleenex tissue). The term “brand name” is a synonym for trademark. In ACS publications, do not use the trademark symbols ™ and ® or the service mark symbol SM. They are not necessary to ensure legal protection for the trademark. ➤ Capitalize trademarks; use them as adjectives with the appropriate nouns. Do not use them in titles. Ficoll Novocain (but novocaine) Plexiglas (but plexiglass) Pyrex Sephadex Styrofoam Teﬂon Triton Tween ➤ In general, however, use generic names rather than trade names. cross-linked dextran polymer beads (not Sephadex) diatomaceous earth (not Celite) 4,4′-isopropylidenediphenol (not Bisphenol A) 2-methoxyethanol (not Methyl Cellosolve) mineral oil (not Nujol) paclitaxel (not Taxol) petroleum jelly (not Vaseline) photocopy (not Xerox) poly(ethylene glycol) (not Carbowax) tensile testing machine (not Instron tester) ➤ Use trademarks as adjectives only, never as nouns or verbs. Because trademarks are adjectives, they do not have plural forms. 158 ➤ The ACS Style Guide Abbreviations and Acronyms An abbreviation is a short form of a word; often the individual letters are pronounced. In an acronym, the letters always form a pronounceable word. ACS is an abbreviation; CASSI is an acronym. A list of ACS-recommended abbreviations, acronyms, and symbols is given in Appendix 10-2. Check the list to ﬁnd an abbreviation. If no abbreviation is listed for the term you are using, you may devise an abbreviation provided that (1) it is not identical to an abbreviation of a unit of measure, (2) it will not be confused with the symbol of an element or a group, (3) it does not hamper the reader’s understanding, and (4) you do not use the same abbreviation for more than one spelled-out form. ➤ If a very long name or term is repeated many times throughout a paper, an abbreviation is warranted. Place the abbreviation in parentheses following the spelled-out form the ﬁrst time it appears in the text. If it is used in the abstract, deﬁne it in the abstract and again in the text. After deﬁning the abbreviation in the text, you may use it throughout the paper. exceptions The following list shows abbreviations that never need to be deﬁned. Refer to Appendix 10-2 for all other abbreviations. a.m. anal. at. wt bp ca. cf. CP DNA e.g. ed., eds. Ed., Eds. eq(s) equiv equiv wt et al. etc. fp GLC i.d. i.e. in. IR m M before noon (Latin ante meridiem) analysis atomic weight boiling point about (Latin circa) compare (Latin confer) chemically pure deoxyribonucleic acid for example (Latin exempli gratia) edition, editions Editor, Editors equation(s) [with number(s)] equivalent(s) [with number(s)] equivalent weight and others (Latin et alii) and so forth (Latin et cetera) freezing point gas–liquid chromatography inside diameter that is (Latin id est) inch, inches infrared molal molar Chapter 10: Editorial Style mmp mp Mr N NMR no., nos. o.d. p, pp p.m. P.O. ref(s) RNA sp., spp. sp gr sp ht sp vol U.K. U.S. USP UV v/v vol vs w/v w/w wt ➤ 159 mixture melting point melting point relative molecular mass (molecular weight) normal nuclear magnetic resonance number, numbers outside diameter page, pages after noon (Latin post meridiem) Post Ofﬁce (with Box and number) reference(s) [with number(s)] ribonucleic acid species, singular and plural speciﬁc gravity speciﬁc heat speciﬁc volume United Kingdom United States United States Pharmacopeia ultraviolet volume per volume volume versus weight per volume weight per weight weight ➤ Avoid abbreviations in the title of a paper. ➤ For some, but not all, abbreviations, case is important; that is, if they are capitalized, they must never be made lowercase; if they are lowercase, they must never be capitalized. This guideline applies to abbreviations that would lose their meanings or change meanings if their forms were changed, such as units of measure (e.g., mg cannot be changed to Mg, min cannot be changed to Min), mathematical symbols (e.g., pH cannot be changed to PH or ph), and chemical symbols (e.g., o for ortho cannot be changed to O). However, if the meaning would not be affected, some abbreviations can be capitalized at the beginning of a sentence and in titles and headings, especially if they are so common that they are more like words than abbreviations. For example, you could use “e-mail” in text and “E-mail” at the beginning of a sentence. ➤ Symbols for the chemical elements are not treated as abbreviations. They need not be deﬁned, and they are typeset in roman type. (See Table 13-1 on p 270 f.) 160 ➤ The ACS Style Guide ➤ Abbreviate units of measure and do not deﬁne them when they follow a number. Without a number, spell them out. 9 V/s or 9 V· s–1 (but measured in volts per second) For exceptions, see p 225. ➤ Abbreviations that are common to a speciﬁc ﬁeld may be permitted without identiﬁcation in books and journals in that ﬁeld only, at the discretion of the editor. ➤ For genus and species names, spell out the full genus name in the title, in the abstract, and the ﬁrst time it appears in text. Abbreviate it thereafter with the same species name, but spell it out again with each different species name. Form the abbreviation with the initial of the genus name. If the paper contains more than one genus name that starts with the same initial letter, devise abbreviations that distinguish them. Use italic type for all names and abbreviations. first time subsequently Bacillus stearothermophilus Bacillus subtilis Escherichia coli Salmonella typhimurium Staphylococcus aureus B. stearothermophilus B. subtilis E. coli S. typhimurium Staph. aureus ➤ Use “e.g.”, “i.e.”, “vs”, and “etc.” only in ﬁgure captions, in tables, and in parentheses in text. Elsewhere, spell out “for example”, “that is”, “versus”, and “and so forth”. ➤ Do not confuse abbreviations and mathematical symbols. An abbreviation is usually two or more letters; a mathematical symbol should generally be only one letter, possibly with a subscript or superscript. An abbreviation may be used in narrative text but seldom appears in equations; a mathematical symbol is preferred in equations and may also be used in text. For example, in text with no equations, PE may be used for potential energy, but in mathematical text and equations, Ep is preferred. Abbreviations are typeset in roman type; most mathematical symbols are typeset in italic type. ➤ In text, spell out all months with or without a speciﬁc day. On August 3, 1996, we completed the second phase of the experiment. The ﬁnal results will be available in January 1997. ➤ Use the following abbreviations (with no periods) or spelled-out forms for months with a day or with a day and year in footnotes, tables, ﬁgure captions, bibliographies, and lists of literature cited. Chapter 10: Editorial Style Jan Feb March April ➤ 161 Sept Oct Nov Dec May June July Aug ➤ Use the abbreviations U.S. and U.K. as adjectives only; spell out United States and United Kingdom as the noun forms in text. Either United Kingdom or U.K. may be used in addresses. U.K. educational system educational system in the United Kingdom U.S. science policy chemical industry in the United States ➤ Form the plurals of multiletter, all-capital abbreviations and abbreviations ending in a capital letter by adding a lowercase “s” only, with no apostrophe. HOMOs JPEGs PAHs PCBs PCs pHs ➤ To avoid ambiguity or poor appearance, add an apostrophe and a lowercase “s” to form the plurals of lowercase abbreviations, single-capital-letter abbreviations, abbreviations ending in a subscript or superscript, and abbreviations ending in an italic letter. cmc’s O’s (or oxygens; Os is the symbol for osmium) pK’s pKa’s Tg’s ➤ Use two-letter abbreviations for U.S. state and territory names and the District of Columbia and for Canadian province and territory names on all letters going through the U.S. Postal Service and most express delivery services. Use them after the name of a city in text, footnotes, and references. u.s. states, territories, and the district of columbia Alabama Alaska American Samoa Arizona Arkansas California AL AK AS AZ AR CA Colorado Connecticut Delaware District of Columbia Federated States of Micronesia Florida CO CT DE DC FM FL 162 ➤ The ACS Style Guide Georgia Guam Hawaii Idaho Illinois Indiana Iowa Kansas Kentucky Louisiana Maine Marshall Islands Maryland Massachusetts Michigan Minnesota Mississippi Missouri Montana Nebraska Nevada New Hampshire New Jersey New Mexico GA GU HI ID IL IN IA KS KY LA ME MH MD MA MI MN MS MO MT NE NV NH NJ NM New York North Carolina North Dakota Northern Mariana Islands Ohio Oklahoma Oregon Palau Pennsylvania Puerto Rico Rhode Island South Carolina South Dakota Tennessee Texas Utah Vermont Virgin Islands Virginia Washington West Virginia Wisconsin Wyoming NY NC ND MP OH OK OR PW PA PR RI SC SD TN TX UT VT VI VA WA WV WI WY canadian provinces and territories Alberta British Columbia Manitoba New Brunswick Newfoundland and Labrador Northwest Territories Nova Scotia AB BC MB NB NL NT NS Nunavut Ontario Prince Edward Island Quebec Saskatchewan Yukon Territory NU ON PE QC SK YT ➤ Spell out and capitalize “company” and “corporation” as part of company names when they appear in an author’s afﬁliation. Abbreviate them elsewhere in text. After the ﬁrst mention, drop Co. and Corp. and use only the company name. ➤➤➤➤➤ APPENDIX 10-1 Computer and Internet Terms This appendix lists the spelling, capitalization, and abbreviations of some common computer and Internet terms. This list is not intended to be exclusive. Alternative choices, in many cases, are acceptable. Proscribed usages are speciﬁcally indicated. An excellent source for deﬁnitions of these terms may be found at http:// www.google.com/. In the search statement, use the syntax “deﬁne:xyz” where xyz is the term for which a deﬁnition is sought. active matrix ADSL (asymmetric digital subscriber line) AI (artiﬁcial intelligence) anonymous FTP applet application archive ASCII (American Standard Code for Information Interchange) ASP (application service provider) asynchronous AVI (audio video interleaved) back up (verb) backup (noun, adjective) bandwidth Base 64 batch processing baud baud rate BBS (bulletin board system) BinHex (binary hexadecimal) BIOS (basic input/output system) bit bitmap Bitnet (Because It’s There NETwork) bitstream blog, blogger bookmark boot bounce (e-mail) bps (bits per second) broadband browser bulletin board byte C (programming language) C++ (programming language) cable modem cache CAD (computer-assisted design) CAD/CAM (computer-assisted design and manufacturing) CCD (charge-coupled device) CD (compact disc) CD key CD-R (compact disc read-only) CD-ROM (compact disc with read-only memory) CD-RW (compact disc read–write) CDMA (code division multiple access) CGI (common gateway interface) CGM (computer graphics metaﬁle) CIF (crystallographic information ﬁle) codec compact disc (CD) compiler CPU (central processing unit) CRT (cathode ray tube) 163 164 ➤ The ACS Style Guide CSS (cascading style sheet) cursor CVC (color video controller) cyberspace daemon data domain data log data parse, data parsing data processing data set database DBMS (database management system) debug (verb) default defragment desktop DHCP (dynamic host conﬁguration protocol) DHTML (dynamic hypertext markup language) dialog box digital signal directory disc (compact disc only) disk (ﬂoppy or hard disk) disk drive disk space diskette DNS (domain name system or server) domain name DOI (digital object identiﬁer) DOS (disk operating system) double-click (as verb) download dpi (dots per inch) drag and drop DSL (digital subscriber line) DTD (document-type deﬁnition) duplex DVD (digital video disc) DVD-R (digital video disc read-only) DVD-RW (digital video disc read–write) e-book e-journal e-mail (electronic mail) e-money e-publish e-zine (electronic magazine) EBCDIC (Extended Binary-Coded Decimal Interchange Code) emoticons encryption end user (noun) EPS (encapsulated PostScript) Ethernet (but an ethernet) extranet FAQ (frequently asked question) FDDI (ﬁber distributed data interface) ﬁber optics ﬁle compression ﬁle name ﬁlter ﬁnger Firefox ﬁrewall FireWire ﬂash memory ﬂoppy disk ﬂowchart format, formatted, formatting Fortran FreeNet (but a freenet) freeware front end FTP (ﬁle transfer protocol) gateway GB (gigabyte, equal to 1024 megabytes; always a space between number and GB) GDDM (graphical data display manager) GDI (graphics device interface) GIF (graphics interchange format) 4GL (fourth-generation language) glyph Google GPIB (general purpose interface bus) graphic (noun) graphical interface Chapter 10: Editorial Style graphics (adjective) graphics conversion graphics ﬁles graphics terminal emulation GUI (graphical user interface) hard disk hard disk drive hardware hardwired high-level-language compiler home directory home page (lowercase, but capitalized when part of a speciﬁc name, e.g., ACS Home Page) hot key hotline HTML (hypertext markup language) HTTP (hypertext transfer protocol) HTTPS (hypertext transfer protocol secure) hyperlink hypermedia hypertext IBM-compatible icon iconization iconize IM (instant messaging) IMAP (Internet message access protocol) information superhighway input integrated circuit interdomain conversion Internet intranet I/O (input/output) IP (Internet protocol) IP address IRC (Internet relay chat) ISDN (integrated services digital network) ISP (Internet service provider) Java Javascript ➤ 165 JDK (Java Development Kit) joystick JPEG (Joint Photographic Experts Group) K (kilobyte, equal to 1024 bytes; always closed up to number; as in 8K or 16K disk drive; kB is preferred) kB (kilobyte, equal to 1024 bytes; always a space between number and kB) KB (kilobyte; kB is preferred) kbps (kilobits per second) kBps (kilobytes per second) keyboard keypad keystroke kilobit kilobyte LAN (local area network) laptop LaTeX (pronounced “lahtek”) LCD (liquid-crystal display) Lexis LexisNexis list-administration software list-management software list owner list server Listserv (software) local area network (LAN) log in, logging in (verb) log off, logging off (verb) log on, logging on (verb) log out, logging out (verb) login name logon name Macintosh, Macintoshes macro, macros mainframe math coprocessor MB (megabyte, equal to 1024 kilobytes; always a space between number and MB) megapixel meta-list 166 ➤ The ACS Style Guide metadata microchip microcomputer, microcomputing microprocessor Microsoft Excel Microsoft PowerPoint Microsoft Windows Microsoft Word MIDI (musical instrument digital interface) MIME (multipurpose Internet mail extension) minicomputer miniﬂoppy disk modem monitor (noun) motherboard motif mouse (plural: mouse devices) Mozilla MP3 (MPEG audio layer 3) MPEG (Motion Picture Experts Group) MS-DOS (Microsoft disk operating system, always hyphenated) MTA (mail-transfer agent) MUA (mail-user agent) multitasking NCP (network control program) NCSA (National Center for Supercomputing Applications) Net (when referring to the Internet; lowercase when referring to any network) netiquette netizen Netscape netware network newsgroup NIC (Network Information Center) NNTP (network news transfer protocol) node, nodes NREN (National Research and Education Network) OCR (optical character recognition) ODBC (open database connectivity) off-site (always hyphenated) ofﬂine (one word in computer context) on-site (always hyphenated) online (one word in computer context) open source OS (operating system) OSX (Macintosh Operating System X) output PageMaker PAM (pulse amplitude modulation) parallel port parser password path PC (personal computer) PCMCIA (Personal Computer Memory Card International Association) pdb (Protein Data Bank) format PDF (portable document format) Perl (programming language) PHP (personal home page) PIF (picture interchange format) pixel plaintext plug and play plug-in PNG (portable network graphics) POP (post ofﬁce protocol) popup PostScript PPP (point-to-point protocol) primary domain print queue programmer, programming PROM (programmable read-only memory) protocol proxy server PSTN (public switched telephone network) pull-down (adjective) QuarkXPress queue QuickTime RAM (random-access memory) raster, rasterize Chapter 10: Editorial Style RDBMS (relational database management system) read/write permission real time (noun) real-time (unit modiﬁer) reboot RFC (request for comments) rich text RJE (remote job entry) ROM (read-only memory) router RPG (report program generator) RSS (rich site summary) RTF (rich text format) run time (noun) run-time (adjective) Safari scale up (verb) scanner screen dump script SCSI (small computer system interface, pronounced “skuzzy”) search engine security certiﬁcate serial communication serial port server servlet set up (verb) setup (noun) SGML (standard generalized markup language) shared user shareware shortcut shut down (verb) shutdown (noun, adjective) sign off (verb) sign-off (noun, adjective) simplex SLIP (serial-line Internet protocol) SMB (server message block) SMDS (switched multimegabit data service) smiley (the :) or  symbol) ➤ 167 SMTP (simple mail transfer protocol) SNMP (simple network management protocol) SOAP (simple object access protocol) software source code spam spelling checker spreadsheet spyware SQL (structured query language) SSL (secure sockets layer) stand-alone (always hyphenated) start up (verb) startup (noun) strikethrough submenu SVGA (super video graphics adapter) systems programs T-1, T-3 TB (terabyte) Tcl (programming language, pronounced “tickle”) TCP (transmission control protocol) TCP/IP (transmission control protocol/ Internet protocol) telecommute Telnet terminal emulation program terminal server TeX (pronounced “tek”) TFT (thin-ﬁlm transistor) throughput TIFF (tagged image ﬁle format) time-sharing (always hyphenated) TLD (top-level domain) toolbar toolbox trackball Trojan horse TTL (transistor–transistor logic) TTY (teletype) UDP (user datagram protocol) UGA (ultra graphics accelerator) Unicode 168 ➤ The ACS Style Guide Unify Unix upload UPS (uninterruptible power source) URC (uniform resource characteristic) URI (uniform resource identiﬁer) URL (uniform resource locator) URN (uniform resource name) USB (universal serial bus) Usenet user id, user ids utility program uuencode (Unix-to-Unix encoding) vector, vectorize VGA (video graphics adapter) video adapter Visual Basic VoIP (voice over Internet protocol) VPN (virtual private network) VRML (virtual reality modeling language) W3C (World Wide Web Consortium) WAIS (wide-area information service or server) WAN (wide-area network) the Web Web browser Web page Web server Web site Webmaster Webzine Wi-Fi (wireless ﬁdelity) window (general term, not speciﬁc program) Windows (Microsoft program) WinZIP word-processing software word processor WordPerfect wordwrap workstation World Wide Web (three words, no hyphens) World Wide Web Consortium (W3C) worm WORM (write once, read many times) WWW (World Wide Web) WYSIWYG (what you see is what you get) Xbase Xenix XML (extensible markup language) ZIP archive ➤➤➤➤➤ APPENDIX 10-2 Abbreviations, Acronyms, and Symbols This list is not intended to be exclusive. Alternative choices, in many cases, are acceptable. Proscribed usages are speciﬁcally indicated. If no abbreviation is listed for the term you are using, you may devise an abbreviation provided that (1) it is not identical to an abbreviation of a unit of measure, (2) it will not be confused with the symbol of an element or a group, (3) it does not hamper the reader’s understanding, and (4) you do not use the same abbreviation for more than one spelled-out form. α [α]tD [α]tλ a a a0 A Å A A.D. a.m. AAS abs ac ac ﬁne structure constant optical rotation stereochemical descriptor speciﬁc rotation at temperature t and wavelength of sodium d line speciﬁc rotation at temperature t and wavelength λ antisymmetric are (unit of area, 100 m2) atto (10–18) axial [use 2(a)-methyl in names] a axis absorptivity axial chirality [as in (aR)-6,6′-dinitrodiphenic acid] Bohr radius (0.52917 Å) adenosine alanine ampere ring (italic in steroid names) angstrom absorbance [as in A = log(l/T)] anticlockwise (chirality symbol) Helmholtz energy mass number anno Domini ante meridiem atomic absorption spectroscopy absolute alternating current anticlinal 169 170 ➤ The ACS Style Guide Ac acac acam AcCh AcChE AcO ACTH Ade Ado ADP AEM AES af AFM AFS AGU ala Ala alt AM AMP amu anal. anhyd ANN ANOVA Ans ansyl antilog AO ap AP APIMS APS aq Ar Ar AR Ara ara-A ara-C arb unit acetyl actinium acetylacetonato (ligand) acetamide (ligand) acetylcholine acetylcholinesterase acetate adrenocorticotropin; adrenocorticotropic hormone adenine adenosine adenosine 5′-diphosphate analytical electron microscopy atomic emission spectroscopy Auger electron spectroscopy audio frequency atomic force microscopy atomic ﬂuorescence spectroscopy anhydroglucose unit alanyl in genetics alanyl, alanine alternating, as in poly(A-alt-B) amplitude modulation adenosine 5′-monophosphate, adenosine 5′-phosphate atomic mass unit [amu, reference to oxygen, is deprecated; u (reference to mass of 12C) should be used] analysis (Anal. in combustion analysis presentations) anhydrous artiﬁcial neural network analysis of variance ansyl 8-anilino-1-naphthalenesulfonyl antilogarithm atomic orbital antiperiplanar appearance potential atmospheric pressure ionization mass spectrometry appearance potential spectroscopy aqueous relative atomic mass (atomic weight) aryl analytical reagent (e.g., AR grade) arabinose adenosine, with arabinose rather than ribose (arabinoadenosine, also ara-A, araA) cytidine, with arabinose rather than ribose (arabinocytidine, also ara-C, araC) arbitrary unit (clinical) Chapter 10: Editorial Style Arg ARPES ARPS as AS Asa ASIS Asn Asp Asx asym at. wt ATCC atm atom % ATP ATPase ATR au AU AUFS av β b b B B B.C. B.C.E. b.i.d. bar bbl bcc bccub BCD Bd BEHP BET BeV arginyl, arginine angle-resolved photoelectron spectroscopy angle-resolved photoelectron spectroscopy asymmetrical absorption spectroscopy β-carboxyaspartic acid aromatic solvent-induced shift asparaginyl, asparagine aspartyl, aspartic acid “Asn or Asp” asymmetrical atomic weight American Type Culture Collection atmosphere atom percent adenosine 5′-triphosphate adenosinetriphosphatase attenuated total reﬂection atomic unit absorbance unit astronomical unit (length) absorbance units at full scale average stereochemical descriptor barn (neutron capture area, 10–24 cm2) bohr (unit of length) broad or broadened (spectra) b axis block, as in poly(A-b-B) “aspartic acid or asparagine” bel buckingham (10–26 esu cm2) ring (italic in steroid names) boat (conformation) before Christ before the common era twice a day unit of pressure; unit and abbreviation are the same barrel body-centered cubic (crystal structure) body-centered cubic (crystal structure) binary coded decimal baud bis(2-ethylhexyl) phthalate Brunauer–Emmett–Teller (adsorption isotherm) billion electronvolts ➤ 171 172 ➤ The ACS Style Guide bGH Bi binap binol biol bipy bis-Tris bit BL BM Bn BN BO BOD bp bps Bps bpy BPY Bq br BSA BSSE Btu bu Bu BWR Bz Bzac Bzl χ c c C bovine growth hormone biot 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (ligand) 1,1′-bi-2-naphthol (ligand) biological(ly) 2,2′-bipyridine, 2,2′-bipyridyl (bpy preferred) 4,4′-bipyridine, 4,4′-bipyridyl (bpy preferred) [bis(2-hydroxyethyl)amino]tris(hydroxymethyl)methane (also bistris, Bis-Tris, bis-tris) binary digit bioluminescence Bohr magneton (use µB) benzyl (also Bzl) bond number Born–Oppenheimer biological oxygen demand base pair boiling point bits per second bytes per second 2,2′-bipyridine, 2,2′-bipyridyl 4,4′-bipyridine, 4,4′-bipyridyl bipyramidal (coordination compounds) becquerel broad or broadened (spectra) bovine serum albumin basis set superposition error British thermal unit bushel butyl Benedict–Webb–Rubin (equation) benzoyl benzoylacetone benzyl (also Bn) magnetic susceptibility candle centered (crystal structure) centi (10–2) cyclo [as in c-C6H11, c-Hx (cyclohexyl)] c axis concentration, for rotation, e.g., [α]20 489 +25 (c 0.13, CHCl3) cyclo [as in c-S6 (cyclo-hexasulfur)] speciﬁc cytochrome (i.e., cytochrome c) Celsius (use °C as unit abbreviation) coulomb cysteine Chapter 10: Editorial Style C C C.E. c/m2 13 C NMR ca. CAD cal calIT calcd CAM cAMP CAN CARS CAT cB Cbz cc CCD CCGC ccp cd CD CDH cDNA CDP CE CE–MS cf. CFC cfm CFSE cfu cgs cgsu ChE CHF Ci CI CIDEP ➤ 173 cytidine ring (italic in steroid names) chair (conformation) clockwise (chirality symbol) common era candles per square meter carbon nuclear magnetic resonance circa, about [used before an approximate date or ﬁgure (ca. 1960)] computer-assisted design calorie International Table calorie calculated computer-assisted manufacturing adenosine cyclic 3′,5′-phosphate adenosine 3′,5′-cyclic phosphate ceric ammonium nitrate coherent anti-Stokes Raman spectroscopy computed axial tomography computer-averaged transients conjugate base, counterbase (also CB) carbobenzoxy, carbobenzyloxy, (benzyloxy)carbonyl, benzyloxycarbonyl (also Z) cubic centimeter (do not use; use cm3 or mL) charge-coupled device capillary column gas chromatography cubic close-packed (crystal structure) candela current density circular dichroism ceramide dihexoside [Cer(Hex)2] complementary DNA cytidine 5′-diphosphate Cotton effect capillary electrophoresis–mass spectrometry compare chloroﬂuorocarbon cubic feet per minute crystal ﬁeld stabilization energy (also cfse) colony-forming units (bacterial inocula) centimeter–gram–second (as in cgs system) centimeter–gram–second unit(s) cholinesterase coupled Hartree–Fock curie chemical ionization conﬁguration interaction chemically induced dynamic electron polarization 174 ➤ The ACS Style Guide CIDNP CIMS CL CM cmc CMH CMO CMP cmr CMR CN CNDO CNS co CoA cod COD coeff colog compd con concd concn const cor cos cosh COSY cot coth counts/s Cp cp cP Cp CP CP/MAS cpd CPE CPK CPL cpm chemically induced dynamic nuclear polarization chemical ionization mass spectrometry cathodoluminescence chemiluminescence carboxymethyl (as in CM-cellulose) critical micelle concentration ceramide monohexoside [Cer(Hex)] canonical molecular orbital cytidine 5′-monophosphate, cytidine 5′-phosphate carbon magnetic resonance (do not use; use 13C NMR) carbon magnetic resonance (do not use; use 13C NMR) coordination number complete neglect of differential overlap central nervous system copoly (as in A-co-B) coenzyme A 1,5-cyclooctadiene (ligand) chemical oxygen demand coefﬁcient cologarithm compound conrotatory (may be italic) concentrated concentration constant corrected cosine hyperbolic cosine correlation spectroscopy cotangent 1,3,5,7-cyclooctatetraene (ligand) hyperbolic cotangent counts per second heat capacity at constant pressure candlepower centipoise cyclopentadienyl chemically pure cross-polarization cross-polarization/magic-angle spinning (also CP-MAS, CP–MAS, CPMAS, CP MAS) contact potential difference controlled-potential electrolysis Corey–Pauling–Koltun (molecular models) creatine phosphokinase circular polarization of luminescence counts per minute Chapter 10: Editorial Style cps CRAMPS CRIMS crit cRNA CRT CRU cryst csc csch CT CTEM CTH CTP CU-8 cub Cv CV CVD CW cwt Cy cyclam Cyd Cys cyt Cyt cytRNA CZE δ ∂ d d. d ➤ 175 counts per second (use counts/s) cycles per second (use Hz or s–1) combined rotation and multiple-pulse spectroscopy chemical reaction interface mass spectrometry critical complementary RNA cathode ray tube constitutional repeating unit crystalline cosecant hyperbolic cosecant charge transfer conventional transmission electron microscopy ceramide trihexoside [Cer(Hex)3] cytidine 5′-triphosphate cubic, coordination number 8 cubic (crystal structure) heat capacity at constant volume coefﬁcient of variation cyclic voltammetry chemical vapor deposition constant width continuous wave (as in CW ESR) hundredweight cyclohexyl 1,4,8,11-tetraazacyclotetradecane cytidine cysteinyl, cysteine cytochrome cytosine cytoplasmic RNA capillary zone electrophoresis NMR chemical shift in parts per million downﬁeld from a standard partial differential day (spelled-out form is preferred) deci (10–1) deoxy deuteron differential (mathematical) diffuse doublet (spectra) diameter, with i. and o. (inside and outside) density dextrorotatory distance spacing (X-ray) 176 ➤ The ACS Style Guide d D D 2-D 3-D da Da daf dAMP dansyl dB dc DD-8 DD NMR DDT de DEAE dec decomp DEFT deg DEG DEHP DES det df DF DFT diam dil dis distd DLVO DMA DMBA DME DMEM DMF DMN dmr absolute conﬁguration aspartic acid debye deuterium ring (italic in steroid names) diffusion coefﬁcient symmetry group [e.g., D3; also used in names, such as (+)-D3-trishomocubane] two-dimensional (also 2D) three-dimensional (also 3D) deca or deka (10) dalton dry ash free 2′-deoxyadenosine 5′-monophosphate or phosphate (the A can be replaced with C, G, U, etc.) 5-(dimethylamino)-1-naphthalenesulfonyl decibel direct current dodecahedral, coordination number 8 dipolar decoupling NMR 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane diastereomeric excess (diethylamino)ethyl (as in DEAE-cellulose) decomposition decompose driven equilibrium Fourier transform degree (use °B, degrees Baumé; °C, °F, but K) diethylene glycol bis(2-ethylhexyl) phthalate (BEHP is preferred) diethylstilbestrol determinant degrees of freedom degrees of freedom density functional theory diameter dilute disrotatory (may be italic) distilled Derjaguin–Landau–Verwey–Overbeek dynamic mechanical analyzer 9,10-dimethylbenz[a]anthracene 1,2-dimethoxyethane dropping mercury electrode Dulbecco’s modiﬁed Eagle’s medium dimethylformamide diaminomaleonitrile deuterium magnetic resonance (do not use; use 2H NMR) Chapter 10: Editorial Style DMR DMSO DMTA DNA DNase DNMR DNP DNPH Dns Dopa DP dpm DPPH dps Dq DQF DRIFT Ds DSC dT Dt DTA DTC dTDP DTE dThd dTMP DTT dTTP dyn ε ε∗ e eaq– e–(aq) es– e–(s) e E deuterium magnetic resonance (do not use; use 2H NMR) dimethyl sulfoxide (also Me2SO) dynamic mechanical thermal analyzer deoxyribonucleic acid deoxyribonuclease dynamic nuclear magnetic resonance deoxynucleoprotein dynamic nuclear polarization (NMR) (2,4-dinitrophenyl)hydrazine dansyl 3-(3,4-dihydroxyphenyl)alanine (also DOPA) degree of polymerization (also dp) disintegrations per minute 2,2-diphenyl-1-picrylhydrazyl disintegrations per second crystal ﬁeld splittings double quantum ﬁltered diffuse reﬂectance Fourier transform crystal ﬁeld splittings differential scanning calorimetry thymidine crystal ﬁeld splittings differential thermal analysis depolarization thermocurrent differential thermal calorimetry thymidine 5′-diphosphate dithioerythritol thymidine thymidine 5′-monophosphate, thymidine 5′-phosphate dithiothreitol thymidine 5′-triphosphate dyne dielectric constant molar absorptivity complex permittivity base of natural logarithm electron equatorial [in names, e.g., 2(e)-methyl] hydrated electron hydrated electron solvated electron solvated electron electronic charge exa (1018) glutamic acid ➤ 177 178 E E° E1/2 E1 E2 e.g. Ea, EA ea0 EC ECD ECE ECG ecl ECL ECP ed. Ed. ED ED50 edda eds. Eds. EDS edta EDTA EDXS ee EEG EELS EFG EGA EGD EGR Eh EH EI EIA Ek ➤ The ACS Style Guide electromotive force energy entgegen (conﬁguration) envelope (conformation) potential energy speciﬁc extinction coefﬁcient (E280nm1%,1cm) Young’s modulus standard electrode potential standard electromotive force half-wave potential ﬁrst-order elimination second-order elimination for example Arrhenius or activation energy electronic charge in electrostatic units × Bohr radius or atomic units for dipole moment exclusion chromatography electron-capture detector, detection electrochemical, chemical, electrochemical (mechanisms) electrocardiogram electrochemical luminescence electrochemical luminescence effective core potential edition, edited editor effective dose dose that is effective in 50% of test subjects (also ED50) ethylenediaminediacetato (ligand) editions editors energy-dispersive system (or spectrometry) ethylenediaminetetraacetato (ligand) ethylenediaminetetraacetic acid, ethylenediaminetetraacetate energy-dispersive X-ray spectrometry enantiomeric excess electroencephalogram electron energy loss spectroscopy electric ﬁeld gradient evolved gas analysis evolved gas detection exhaust gas recirculation hartree (unit); Hartree energy extended Hückel electron impact electron ionization enzyme immunoassay kinetic energy Chapter 10: Editorial Style EKC EKG EL ELISA e/m EM e-mail EMC emf EMIS emu en ENDOR ent Ep EPA epi EPMA EPR EPXMA eq equiv equiv wt erf erfc erfc–1 ESCA esd ESE ESEEM ESI ESIMS ESP ESR esu Et et al. etc. eu EU eV EXAFS exch exp expt exptl ➤ 179 electrokinetic chromatography electrocardiogram electroluminescence enzyme-linked immunosorbent (immunoadsorbent) assay ratio of electron charge to mass electron microscopy electronic mail equilibrium moisture content electromotive force electromagnetic isotope separation electromagnetic unit ethylenediamine (ligand) electron–nuclear double resonance reversal of stereocenters potential energy ether–isopentane–ethanol (solvent system) inversion of normal conﬁguration (italic with a number, as in 15-epiprostaglandin A) electron probe microanalysis electron paramagnetic resonance electron probe X-ray microanalysis equation equivalent equivalent weight error function error function complement inverse error function complement electron spectroscopy for chemical analysis estimated standard deviation electron spin echo electron spin echo envelope modulation electrospray ionization electrospray ionization mass spectrometry elimination of solvation procedure electron spin resonance electrostatic unit ethyl and others and so forth entropy unit enzyme unit electronvolt extended X-ray absorption ﬁne structure exchangeable (spectra) exponential experiment experimental 180 ➤ The ACS Style Guide f f F F FAAS FABMS fac FAD FAES FAFS FAS fcc FCC Fd FEM FES ff FFEM FFF FFS FFT FHT FI FIA ﬁd FID FIK FIR FLC fm FM FMN FMO and page following (as in p 457 f) femto (10–15) fermi (unit of length, also fm) ﬁne (spectral) focal length frequency (in statistics) function [as in f(x)] furanose form Fahrenheit (use °F as unit abbreviation) farad formal (use judiciously; M is preferred) phenylalanine Faraday constant variance ratio (in statistics) ﬂame atomic absorption spectroscopy fast atom bombardment mass spectrometry facial ﬂavin adenine dinucleotide ﬂame atomic emission spectroscopy ﬂame atomic ﬂuorescence spectroscopy ﬂame absorption spectroscopy face-centered cubic (crystal structure) ﬂuid catalytic cracking ferredoxin ﬁeld emission microscopy or spectroscopy ﬁeld emission spectroscopy ﬂame emission spectrometry and pages following (as in p 457 ff) freeze–fracture electron microscopy ﬁeld ﬂow fractionation ﬂame ﬂuorescence spectroscopy fast Fourier transform Fisher–Hirschfelder–Taylor (space-ﬁlling models) ﬁeld ionization ﬂow-injection analysis ﬂuorescence immunoassay free induction decay (in Fourier transform work) ﬂame ionization detector, detection free induction decay (in Fourier transform work) ﬁeld ionization kinetics far-infrared ferroelectric liquid crystal femtometer fermi (unit of length, also f) frequency modulation ﬂavin mononucleotide frontier molecular orbital Chapter 10: Editorial Style FOPPA fp FPC FPT Fr Fr Fru FSGO FSH ft FT ft-c ft-lb ft-lbf FTICR FTIR FTIRS FTP FTS Fuc fw fwhh fwhm ﬁrst-order polarization propagator approach freezing point ﬁxed partial charge ﬁnite perturbation theory franklin Froude number fructose ﬂoating spherical Gaussian orbital follicle-stimulating hormone foot Fourier transform foot-candle foot-pound foot-pound-force Fourier transform ion cyclotron resonance Fourier transform infrared (also FT/IR, FT-IR, and FT IR) Fourier transform infrared spectroscopy ﬁle transfer protocol Fourier transform spectroscopy fucose formula weight full width at half-height full width at half-maximum γ microgram (use µg) photon surface tension surface concentration gas [as in H2O(g)] gram acceleration due to gravity (closed up to number preceding) splitting factor (ESR and NMR spectroscopy) gauss generally labeled giga (109) glycine guanosine Gibbs energy gravitational constant gram-atom (use mol) Galileo number gallon galactose galileo (unit of acceleration) N-acetylgalactosamine gas chromatography gas displacement chromatography Γ g g G G g-atom Ga gal Gal GalNAc GC GDC ➤ 181 182 ➤ The ACS Style Guide GDMS GDP gem GFAAS GFC gfw GH GHz Gi GIAO Glc GLC GlcNAc Gln GLPC Glu Glx gly Gly GMP GPC gr GSC GSH GSL GSSG GTP Gua Guo Gy glow discharge mass spectrometry guanosine 5′-diphosphate geminal graphite furnace atomic absorption spectroscopy gas frontal chromatography gram formula weight growth hormone (somatotropin) gigahertz gilbert gauge-invariant atomic orbital glucose gas–liquid chromatography N-acetylglucosamine glutaminyl, glutamine gas–liquid partition chromatography glutamyl, glutamic acid “Gln or Glu” glycine (ligand) glycyl, glycine guanosine 5′-monophosphate, guanosine 5′-phosphate gel permeation chromatography grain (unit of weight) gas–solid chromatography reduced glutathione glycosphingolipid oxidized glutathione guanosine 5′-triphosphate guanine guanosine gray (international unit of absorbed dose) η hapto viscosity hecto (102) helion hour crystallographic index (hkl) Planck’s constant Planck’s constant divided by 2π henry histidine enthalpy half-chair (conformation) Hamiltonian Hamiltonian proton nuclear magnetic resonance h h  H H  1 H NMR Chapter 10: Editorial Style 2 H NMR H0 ha Hb Hbg HCG hcp HCP HCS HDPE Hedta H2edta H3edta H4edta HEEDTA Hepes Hepps hex HF hfs hfsc hGH HIPS His HIV hkl HMDS HMO HMPA HMPT hnRNA hν HOHAHA HOMO H2ox hp HPCE HPLC HREELS HREM HRMS HSP ➤ 183 deuterium nuclear magnetic resonance magnetic ﬁeld (ESR and NMR spectroscopy) hectare hemoglobin biguanide human chorionic gonadotropin hexagonal close-packed (crystal structure) hexachlorophene hazard communication standard high-density polyethylene ethylenediaminetetraacetate(3–) (-ato as ligand in full name) ethylenediaminetetraacetate(2–) (-ato as ligand in full name) ethylenediaminetetraacetate(1–) (-ato as ligand in full name) ethylenediaminetetraacetic acid N-(2-hydroxyethyl)ethylenediaminetriacetate N-(2-hydroxyethyl)piperazine-N′-ethanesulfonic acid (also HEPES, hepes) N-(2-hydroxyethyl)piperazine-N′-propanesulfonic acid (also HEPPS, hepps) hexagonal (crystal structure) Hartree–Fock hyperﬁne splitting hyperﬁne splitting constant human growth hormone high-impact polystyrene histidyl, histidine human immunodeﬁciency virus crystallographic index hexamethyldisilane hexamethyldisiloxane Hückel molecular orbital hexamethylphosphoramide hexamethylphosphoric triamide heterogeneous nuclear RNA indicates light; h is Planck’s constant, and ν is the photon frequency homonuclear Hartmann–Hahn highest occupied molecular orbital oxalic acid horsepower high-performance capillary electrophoresis high-performance liquid chromatography high-pressure liquid chromatography high-resolution electron energy loss spectroscopy high-resolution electron microscopy high-resolution mass spectrometry heat shock protein 184 ➤ The ACS Style Guide Hyl Hyp Hz i i I I i.d. i.e. I/O ibid. ic IC ICP ICR ics ICSH ICT id ID ID50 IDAS IDMS IDP IE IEC IEF IEP IETS IFQ IKES Ile ILS im IMMA IMP in. INDO INDOR hydroxylysyl, hydroxylysine hydroxyprolyl, hydroxyproline hypoxanthine hertz (–1)1/2 iso (as in i-Pr; do not use i-propyl) inosine isoleucine electric current (also i) ionic strength moment of inertia spin quantum number (ESR and NMR spectroscopy) inside diameter that is input–output in the same place (in the reference cited; use is discouraged) intracerebrally integrated circuit ion chromatography inductively coupled plasma ion cyclotron resonance internal chemical shift interstitial-cell-stimulating hormone International Critical Tables diffusion current infective dose dose that is infective in 50% of test subjects (also ID50) isotope dilution α spectrometry isotope dilution mass spectrometry inosine 5′-diphosphate ionization energy ion-exchange chromatography isoelectric focusing isoelectric point inelastic electron-tunneling spectroscopy interfacial ﬂuorescence quenching ion kinetic energy spectroscopy isoleucyl, isoleucine increased life span intramuscularly ion microprobe mass analysis inosine 5′-monophosphate, inosine 5′-phosphate inch intermediate neglect of differential overlap internal nuclear double resonance internucleus (nucleus–nucleus) double resonance Chapter 10: Editorial Style INH ➤ 185 IU iv inhibitor isonicotinic acid hydrazide inosine iterative natural orbital insoluble intraperitoneally ionization potential iron pipe size infrared intermediate retention of differential overlap immunoradiometric assay isotopic ratio mass spectrometry internal reﬂection photolysis infrared reﬂection–absorption spectroscopy internal reﬂection spectroscopy intersystem crossing ionization spectroscopy for chemical analysis ion-selective electrode inversion of normal chirality (not as in isopropyl, but in uses such as 8-iso-prostaglandin E1; generally italic with a number) ion-scattering spectroscopy inosine 5′-triphosphate isotachophoresis international unit intravenous, intravenously J J JT joule coupling constant (NMR and ESR spectroscopy) Jahn–Teller k k kilo (103) Boltzmann constant (also kB) crystallographic index (hkl) rate constant 1000 (as in 60K protein) kayser (use cm–1) kelvin (do not use °K) kilobyte (kB is preferred) lysine equilibrium constant spectral line katal (unit of enzyme catalytic activity) spectral line Boltzmann constant kilobase kilobit Ino INO insol ip IP ips IR IRDO IRMA IRMS IRP IRRAS IRS isc ISCA ISE iso ISS ITP K K Kα kat Kβ kB kb 186 ➤ The ACS Style Guide kB kbar kbp kD kDa KE kg kgf kHz Km Koc Kow KSP Kw λ λex λmax l l l L LI LII LIII Lac LAMMA lat lb lbf LC LCAO LCD LCICD LCVAO LD LD50 LDH LDMS LE kilobel kilobyte kilobar kilobase pair kilodebye kilodalton kinetic energy kilogram kilogram-force kilohertz Michaelis constant carbon-referenced sediment partition coefﬁcient organic chemicals partition coefﬁcient octanol–water partition coefﬁcient solubility product constant autoionization constant absolute activity microliter (use µL) wavelength excitation wavelength wavelength of maximum absorption liquid [as in NH3(l)] crystallographic index (hkl) levorotatory absolute conﬁguration leucine ligand liter spectral line spectral line spectral line lactose laser microprobe mass spectrometry latitude pound pound-force liquid chromatography linear combination of atomic orbitals liquid-crystal display liquid-crystal-induced circular dichroism linear combination of virtual atomic orbitals lethal dose dose that is lethal to 50% of test subjects (also LD50) lactic dehydrogenase laser desorption mass spectrometry locally excited Chapter 10: Editorial Style LED LEED LEEDS LEISS LEMF Leu LFER LH LIF lim LIMS LIS lit. LJ, L-J LLC lm LMCT ln LNDO log Log long. Lp Lp LSC LSD LSR LUMO lut Lut lx LYP Lys light-emitting diode low-energy electron diffraction low-energy electron diffraction spectroscopy low-energy ion-scattering spectroscopy local effective mole fraction leucyl, leucine linear free-energy relationship luteinizing hormone laser-induced ﬂuorescence limit laboratory information management system lanthanide-induced shift literature Lennard-Jones liquid–liquid chromatography lumen ligand-to-metal charge transfer natural logarithm local neglect of differential overlap logarithm to the base 10 principal logarithm longitude Lorentz–polarization (effect) Lorentz factor × polarization factor liquid–solid chromatography lysergic acid diethylamide lanthanide shift reagent lowest unoccupied molecular orbital lutidine (ligand) lutidine lux Lee–Yang–Parr lysyl, lysine µ chemical potential dipole moment electrophoretic mobility micro (10–6) micron (do not use; use µm or micrometer) muon Bohr magneton nuclear magneton Weiss magneton medium (spectra) meter mile (in mpg and mph; otherwise mi) milli (10–3) µ± µB µN µW m ➤ 187 188 m m ➤ The ACS Style Guide multiplet (spectra) isotopic mass magnetic quantum number (ESR and NMR spectroscopy) meta molal (mol kg–1) M mega (106) mesomeric metal (do not use Me) methionine molar (mol dm–3, mol L–1) M minus (left-handed helix) [M] molecular rotation m/e mass-to-charge ratio (m/z is preferred) mAb monoclonal antibody (also Mab, MAb) Mal maltose MALDI matrix-assisted laser desorption ionization MALDI-TOFMS matrix-assisted laser desorption ionization time-of-ﬂight mass spectrometry (also MALDI-TOF MS) Man mannose MAO monoamine oxidase MAS magic-angle spinning MASS magic-angle sample spinning max maximum Mb myoglobin MBE molecular beam epitaxy MCD magnetic circular dichroism mCi millicurie MCT mercury cadmium telluride MD molecular dynamics me electron rest mass Me methyl (not metal) MED mean effective dose MEKC micellar electrokinetic capillary chromatography MEM minimum Eagle’s essential medium mequiv milliequivalent mer polymer notation (as in 16-mer) mer meridional Mes mesityl (2,4,6-trimethylphenyl), 2-morpholinoethanesulfonic acid, 2-morpholinoethanesulfonate (also MES) Met methionyl, methionine MetHb methemoglobin MetMb metmyoglobin MeV million electronvolts mho reciprocal ohm (Ω–1 is preferred) MHz megahertz mi mile Chapter 10: Editorial Style min MINDO MIR MIRS ML MLCT MLR mmHg mmp mmu mn Mn MO mol mol % molar equiv mol wt MOM mon mp mp MP MP2 mpg mph MPI MPV MQ ENDOR Mr MR MRI mRNA Ms MS MSDS MSG MSH Mt MTD mtDNA mtRNA mu minimum minute modiﬁed intermediate neglect of differential overlap mid-infrared multiple internal reﬂection spectroscopy monolayer metal-to-ligand charge transfer multiple linear regression millimeters of mercury (measure of pressure) mixture melting point millimass unit neutron rest mass number-average molecular weight molecular orbital mole mole percent molar equivalent molecular weight (Mr is preferred) methoxymethyl monoclinic (crystal structure) proton rest mass melting point Møller–Plesset second-order Møller–Plesset perturbation theory miles per gallon miles per hour multiphoton ionization Meerwein–Ponndorf–Verley multiple-quantum electron nuclear double resonance relative molecular mass (molecular weight) molecular refraction magnetic resonance imaging messenger RNA mesyl (methylsulfonyl) mass spectrometry mass spectrum microwave spectroscopy manufacturer’s safety data sheet material safety data sheet monosodium glutamate melanocyte-stimulating hormone, melanotropin megaton mean therapeutic dose mitochondrial DNA mitochondrial RNA mass unit ➤ 189 190 ➤ The ACS Style Guide MVA MVS Mw MW MWD Mx Mz m/z mevalonic acid multiple-variable storage weight-average molecular weight molecular weight (Mr is preferred) molecular weight distribution maxwell z-average molecular weight mass-to-charge ratio ν ∼ ν ν1/2 νe νmax frequency wavenumber full width at half-maximum height (NMR spectra) neutrino frequency of maximum absorption nano (10–9) neutron normal (as in n-butyl, n-Bu) refractive index (n20 D, at 20 °C, Na D line) total number of individuals asparagine newton normal (concentration) unspeciﬁed nucleoside nota bene (note well) Avogadro’s number neutron activation analysis sodium ion activated ATPase (also Na-ATPase, NaATPase) nicotinamide adenine dinucleotide reduced nicotinamide adenine dinucleotide nicotinamide adenine dinucleotide phosphate reduced nicotinamide adenine dinucleotide phosphate sodium and potassium ion activated ATPase (also Na,K-ATPase) N-bromosuccinimide New Drug Application neglect of diatomic differential overlap nuclear DNA nonempirical molecular orbital neutralization equivalent normal hydrogen electrode near-infrared norleucyl, norleucine nonlinear optical (optics) nanometer nuclear magneton (use µN) nicotinamide mononucleotide nuclear magnetic resonance (do not use nmr) number n n N N.B. NA NAA [Na]ATPase NAD NADH NADP NADPH [Na,K]ATPase NBS NDA NDDO nDNA NEMO neut equiv NHE NIR Nle NLO nm NM NMN NMR no. Chapter 10: Editorial Style NO NOCOR NOE NOESY NOx Np NPR NQR nRNA NRTL NSOM NTP Nuc Nva ω Ω o O o.d. o-rh o/w O/W OAc obsd OC-6 OCR OD ODMR ODU Oe OES OFDR OMVPE Ord ORD Orn Oro ORTEP osm OTTLE ox oxidn oz natural orbital (as in CNDO/2-NO) neglect of core orbitals nuclear Overhauser effect nuclear Overhauser enhancement spectroscopy nitrogen oxides neper net protein retention nuclear quadrupole resonance nuclear RNA nonrandom two-liquid near-ﬁeld scanning optical microscopy normal temperature and pressure unspeciﬁed nucleoside 5′-triphosphate nucleoside (unspeciﬁed) norvalyl, norvaline angular frequency ohm ortho orotidine outside diameter orthorhombic (crystal structure) oil in water (emulsion) oil in water (emulsion) acetate observed octahedral, coordination number 6 optical character recognition optical density optically detected magnetic resonance optical density unit oersted optical emission spectroscopy off-frequency decoupling resonance organometallic vapor-phase epitaxy orotidine optical rotary dispersion ornithyl, ornithine orotic acid Oak Ridge thermal ellipsoid plot osmolar (also osM, Osm) optically transparent thin-layer electrode oxalato (ligand) oxidized or oxidation (in subscripts and superscripts) oxidation ounce ➤ 191 192 ➤ The ACS Style Guide % ‰ π π± π0 ψ ψrd p p P P p.m. P450 P-450 P450 31 P NMR Pa PAC PAD PAGE paH PAH PAN PBS pc PC PCB PCDD PCDF PCILO PCP PCR PCTFE percent per thousand (parts per thousand) pros (near) in NMR measurements (as in Nπ of histidine) type of orbital, electron pion pion pseudouridine pseudouridine negative logarithm (as in pH) page pico (10–12) proton angular momentum (ESR and NMR spectroscopy) para probability (in statistics) pyranose form peta (1015) poise proline plus (right-handed helix) probability (in statistics) post meridiem speciﬁc cytochrome designation (i.e., cytochrome P450) speciﬁc cytochrome designation (i.e., cytochrome P-450) speciﬁc cytochrome designation (i.e., cytochrome P450) phosphorus-31 nuclear magnetic resonance pascal perturbed angular correlation perturbed angular distribution polyacrylamide gel electrophoresis negative logarithm of hydrogen ion activity polycyclic aromatic hydrocarbon polyacrylonitrile phosphate-buffered saline parsec (unit of length) paper chromatography personal computer planar chromatography polychlorobiphenyl, polychlorinated biphenyl polychlorinated dibenzo-p-dioxin polychlorodibenzo-p-dioxin polychlorodibenzofuran perturbed conﬁguration interaction with localized orbitals pentachlorophenol polymerase chain reaction poly(chlorotriﬂuoroethylene) Chapter 10: Editorial Style PDL PDMS PE PEG PEL PEO PES PET PETP PFU PG pH Ph Phe phen phr Pi PIB PIXE pK pKa PL PLOT PMMA PMO PMR PNA PNDO po POM POPOP pp PP ppb ppbv PPi ppm ppmv PPO PPP PPS ppt pumped dye laser plasma desorption mass spectrometry polyethylene potential energy poly(ethylene glycol) permissible exposure limit poly(ethylene oxide) photoelectron spectroscopy positron emission tomography poly(ethylene terephthalate) plaque-forming unit prostaglandin negative logarithm of hydrogen ion concentration phenyl (for C6H5 only) phenylalanyl, phenylalanine 1,10-phenanthroline, o-phenanthroline parts per hundred parts of resin (or rubber) inorganic phosphate polyisobutylene proton-induced X-ray emission negative logarithm of equilibrium constant pK for association photoluminescence porous-layer open-tubular poly(methyl methacrylate) perturbational molecular orbital phosphorus magnetic resonance (do not use; use 31P NMR) polymerization of monomeric reactants proton magnetic resonance (do not use; use 1H NMR) polynuclear aromatic hydrocarbon partial neglect of differential overlap per os (orally) poly(oxymethylene), polyformaldehyde 1,4-bis(5-phenyl-2-oxazolyl)benzene pages polypropene parts per billion parts per billion by volume inorganic pyrophosphate, phosphoric acid parts per million parts per million by volume 2,5-diphenyloxazole Pariser–Parr–Pople photophoretic spectroscopy parts per trillion precipitate ➤ 193 194 ➤ The ACS Style Guide pptv Pr PRDDO prepn PRFT Pro pro-R pro-S PRT Ps PS psi psia psig pt PTV PU PVA PVAC PVAL PVC PVDC PVDF PVE PVF PXRD py Py PY Py–GC–MS pyr pyrr pz parts per trillion by volume propyl partial retention of diatomic differential overlap preparation partially relaxed Fourier transform prolyl, proline stereochemical descriptor (also pro-R) stereochemical descriptor (also pro-S) platinum resistance thermometer positronium polystyrene pounds per square inch pounds per square inch absolute pounds per square inch gauge pint point phase-transfer catalysis poly(tetraﬂuoroethylene) parathyroid hormone phenylthiohydantoin programmed-temperature vaporizer polyurethane poly(vinyl alcohol) poly(vinyl acetate) poly(vinyl alcohol) poly(vinyl chloride) poly(vinylidene dichloride) poly(vinylidene diﬂuoride) poly(vinyl ether) poly(vinyl ﬂuoride) powder X-ray diffraction pyridine (ligand) pyridine pyramidal (coordination compounds) pyrolysis–gas chromatography–mass spectrometry pyrazine (ligand) pyrrolidine (ligand) pyrazole (ligand) q q Q Q QCPE QELS QSAR qt quartet (spectra) heat, electric charge (also Q) glutamine heat, electric charge (also q) Quantum Chemistry Program Exchange quasi-elastic light scattering quantitative structure–activity relationship quart PTC PTFE PTH Chapter 10: Editorial Style ρ r R R rac rad RBS rd RDE re re recryst red redn redox ref rel rel REL rem REM rep rf Rf RFC RH Rha RI RIA Rib RIMS RIS rms RNA RNase ROA RPLC rpm RQ RRDE ➤ 195 density correlation coefﬁcient arginine Rankine (temperature scale, use °R as unit abbreviation) roentgen gas constant rectus (conﬁgurational) regression coefﬁcient resistance racemic radian unit of radiation Rutherford backscattering spectrometry rad rotating disk electrode electron radius stereochemical descriptor (as in the re face) recrystallized reduced or reduction (in subscripts and superscripts) reduction reduction–oxidation reference relative relative (stereochemical descriptor) recommended exposure limit roentgen equivalent man rapid eye movement roentgen equivalent physical radio frequency retention factor (ratio of distance traveled by the center of a zone to the distance simultaneously traveled by the mobile phase) request for comments relative humidity rhamnose refractive index radioimmunoassay ribose resonance ionization mass spectrometry resonance ionization spectrometry root mean square ribonucleic acid ribonuclease Raman optical activity reversed-phase liquid chromatography revolutions per minute respiratory quotient rotating ring-disk electrode 196 ➤ The ACS Style Guide RRKM rRNA RRS RRT RS RSD Ry σ Σ s s s020,w s2 S S S/N SAM SANS SAPR-8 sar Sar SAR SARISA SAXS sc sc sccm SCE SCF SCF–HF Rice–Ramsperger–Kassel–Marcus ribosomal RNA resonance Raman spectroscopy relative retention time Raman spectroscopy relative standard deviation risk-speciﬁc dose rydberg standard deviation surface charge density surface tension tensile strength type of orbital, electron summation second single bond [as in s-cis (italic in compound names)] singlet (spectra) solid [as in NaCl(s)] strong (spectra) secondary (as in s-Bu; but sec-butyl) sedimentation coefﬁcient standard deviation (analytical) symmetrical sedimentation coefﬁcient measured at 20 °C in water and extrapolated to 0 °C sample variance serine siemens entropy sinister (conﬁgurational) skew (conformation) signal-to-noise ratio self-assembled monolayer small-angle neutron scattering square antiprismatic, coordination number 8 sarcosine (N-methylglycine) (ligand) sarcosyl, sarcosine (N-methylglycine) structure–activity relationship surface analysis by resonance ionization of sputtered atoms small-angle X-ray scattering (or spectroscopy) subcutaneously synclinal standard cubic centimeters per minute saturated calomel electrode self-consistent ﬁeld self-consistent ﬁeld, Hartree–Fock Chapter 10: Editorial Style scfh SCOT SD SDS SE SE2 sec sec SEC sech SECM SECS SEM Ser SERS SEW Sex SFC sh Sh SHC SHE si SI SIM SIMS sin sinh SLR SMOSS SMSI sn SN SN1 SN2 SNi SNO sol soln sp sp. sp SP-4 sp gr standard cubic feet per hour support-coated open-tubular standard deviation sodium dodecyl sulfate standard error second-order electrophilic substitution secant secondary (as in sec-butyl; but s-Bu) size exclusion chromatography hyperbolic secant scanning electrochemical microscopy simulation and evaluation of chemical synthesis scanning electron microscopy standard error of the mean seryl, serine surface-enhanced Raman spectroscopy (or scattering) surface electromagnetic wave exciplex substitution supercritical-ﬂuid chromatography sharp (spectra) shoulder (spectra) Sherwood number shape and Hamiltonian constant standard hydrogen electrode stereochemical descriptor (as in the si face) International System of Units (Système International) secondary ion (as in SIMS) selected-ion monitoring secondary-ion mass spectrometry sine hyperbolic sine spin–lattice relaxation surface Mössbauer strong metal support interaction stereospeciﬁc numbering separation number ﬁrst-order nucleophilic substitution second-order nucleophilic substitution internal nucleophilic substitution semiempirical natural orbital solid solution speciﬁc species (singular) synperiplanar square planar, coordination number 4 speciﬁc gravity ➤ 197 198 ➤ The ACS Style Guide sp ht sp vol SPECT spp. SPR SPY-5 sq SQF SQUID sr SRN1 SRS SSC St std STEM STM STO STO-3G STP subsp. Suc Sv SVL swg sym τ θ [θ] Θ t t t1/2 T speciﬁc heat speciﬁc volume single-photon-emission computed tomography species (plural) stroboscopic pulse radiolysis square pyramidal, coordination number 5 square single quantum ﬁltered superconducting quantum interference device steradian ﬁrst-order nucleophilic substitution triggered by electron transfer stimulated Raman scattering standard saline citrate (NaCl–citrate) stokes standard scanning transmission electron microscopy scanning tunneling microscopy Slater-type orbital Slater-type orbital, three Gaussian standard temperature and pressure subspecies sucrose sievert svedberg single vibrational level standard wire gauge symmetrical tele (far) in NMR measurements (as in Nτ of histidine) angle ORD measurement, deg cm2/dmol temperature (e.g., in Curie–Weiss expressions) metric ton triplet (spectra) triton Student distribution (the Student t test in statistics) temperature (in degrees Celsius) tertiary (as in t-Bu; but tert-butyl) time half-life ribosylthymine tautomeric tera (1012) tesla threonine tritium Chapter 10: Editorial Style T T-4 T/C tan tan δ tanh TBP TBPY-5 TCA TCD TCP/IP TDS TEA TEAE TEM temp tert tetr TFA Tg TGA Tham THC Thd theor THF Thr Thy TIMS TIP TL TLC TMA TMS TMV TnL TOC TOD TOFMS tol TOM Torr temperature (in kelvins) twist (conformation) tetrahedral, coordination number 4 treated vs cured tangent mechanical loss factor hyperbolic tangent tri-n-butyl phosphate trigonal bipyramidal, coordination number 5 tricarboxylic acid cycle (citric acid cycle, Krebs cycle) trichloroacetic acid thermal conductivity detector transmission control protocol/Internet protocol total dissolved solids tetraethylammonium transversely excited atmospheric triethylaminoethyl (as in TEAE-cellulose) transmission electron microscopy temperature tertiary (as in tert-butyl; but t-Bu) tetragonal (crystal structure) triﬂuoroacetyl glass-transition temperature thermogravimetric analysis tris(hydroxymethyl)aminomethane (also Tris) tetrahydrocannabinol ribosylthymine theoretical tetrahydrofuran threonyl, threonine thymine thermal ionization mass spectrometry temperature-independent paramagnetism triboluminescence thin-layer chromatography thermomechanical analysis tetramethylsilane trimethylsilyl tobacco mosaic virus tunnel luminescence total organic carbon total oxygen demand time-of-ﬂight mass spectrometry (also TOF MS) tolyl (also Tol) transmitted optical microscopy torr ➤ 199 200 ➤ The ACS Style Guide tosyl TPD TPDE TPR TPR-6 TQMS tR tr Tr tric triﬂate trig TRIR Tris tRNA Trp Ts TSC TSH tu TVA Tyr 4-toluenesulfonyl (also Ts) temperature-programmed desorption temperature-programmed decomposition temperature-programmed reduction trigonal prismatic, coordination number 6 triple-quadrupole mass spectrometry retention time trace trace triclinic (crystal structure) triﬂuoromethanesulfonate trigonal (crystal structure) time-resolved infrared tris(hydroxymethyl)aminomethane (also Tham) transfer RNA tryptophyl, tryptophan tosyl (4-toluenesulfonyl) thermal stimulated current thyroid-stimulating hormone thiourea (ligand) thermal volatilization analysis tyrosyl, tyrosine u U uniﬁed atomic mass unit uniformly labeled uridine internal energy upper critical solution temperature uridine 5′-diphosphate ultrahigh frequency ultrahigh frequency unrestricted Hartree–Fock ultrahigh vacuum ultra-large-scale integration uridine 5′-monophosphate, uridine 5′-phosphate uncorrected unsymmetrical ultraviolet photoelectron spectroscopy urea (ligand) uracil uridine United States Pharmacopeial Convention uridine 5′-triphosphate ultraviolet ultraviolet photoelectron spectroscopy ultraviolet–visible U UCST UDP uhf UHF UHV ULSI UMP uncor uns UPS ur Ura Urd USP UTP UV UV PES UV–vis Chapter 10: Editorial Style v v V v/v Val VASS VB VCD VDT VEELS VESCF vhf VHF vic vis viz. VLE VLSI VOA VOC vol vol % vp VPC VPO VRML vs VSIP VUV VVk vw w w W W w/v w/w WAN WAXS vendeko (10–30) scan rate velocity valine vendeca (1030) volt volume per volume valyl, valine variable-angle sample spinning valence bond vibrational circular dichroism video display terminal vibrational electron energy loss spectroscopy variable electronegativity self-consistent ﬁeld very high frequency very high frequency vicinal visible namely vapor–liquid equilibrium very large scale integration vibrational optical activity volatile organic compound volume volume percent vapor pressure vapor-phase chromatography vapor pressure osmometry virtual reality modeling language versus (v in legal expressions) very strong (spectra) valence-state ionization potential vacuum ultraviolet Van Vleck very weak (spectra) weak (spectra) weighting factor work tryptophan watt work weight per volume weight per weight wide-area network wide-angle X-ray scattering ➤ 201 202 ➤ The ACS Style Guide Wb WCOT WDS WHSV WLF wt wt % weber wall-coated open-tubular wavelength-dispersive spectroscopy weight-hourly space velocity Williams–Landel–Ferry (molecular models) weight weight percent x x X xenno (10–27) x axis xanthosine (use N for unknown nucleoside) xenna (1027) xanthine X-ray absorption near-edge spectroscopy X-ray absorption near-edge structure xanthosine X-ray energy-dispersive spectrometry X-ray emission spectroscopy xanthosine 5′-monophosphate, xanthosine 5′-phosphate X-ray photoelectron spectroscopy X-ray diffraction X-ray radial distance function X-ray ﬂuorescence xylose Xan XANES Xao XEDS XES XMP XPS XRD XRDF XRF Xyl y y Y yocto (10–24) y axis tyrosine yotta (1024) z z zepto (10–21) charge number of an ion z axis benzyloxycarbonyl (also Cbz) “glutamic acid or glutamine” zetta (1021) atomic number zusammen (conﬁgurational) zero-ﬁeld splitting zero-ﬁeld-splitting constant Z Z zfs zfsc ➤➤➤➤➤ CHAPTER 11 Numbers, Mathematics, and Units of Measure Numbers Both numerals and words can be used to express numbers. The usage and style conventions for numerals and words are different for technical and nontechnical material. Numeral and Word Usage ➤ Use numerals with units of time or measure, and use a space between the numeral and the unit, except %, $, ° (angular degrees), ′ (angular minutes), and ″ (angular seconds). 6 min 0.30 g 273 K 90 °F 25 mL 125 V/s 50% $250 47°8′23″ 180° (but 180 °C) 50 µg of compound/dL of water exception Spell out numbers with units of measure used in a nontechnical sense. If you take ﬁve minutes to read this article, you’ll be surprised. ➤ With items other than units of time or measure, use words for cardinal numbers less than 10; use numerals for 10 and above. Spell out ordinals “ﬁrst” through “ninth”; use numerals for 10th or greater. three ﬂasks 30 ﬂasks Copyright 2006 American Chemical Society 203 204 ➤ The ACS Style Guide third ﬂask seven trees eighth example ﬁrst century sixfold 12th ﬂask 10 trees 33rd example 21st century 20-fold exception 1 Use all numerals in a series or range containing numbers 10 or greater, even in nontechnical text. 5, 8, and 12 experiments 2nd and 20th samples 5–15 repetitions exception 2 Use all numerals for numbers modifying nouns in parallel construction in the same sentence if one of the numbers is 10 or greater. Activity was reduced in 2 pairs, not signiﬁcantly changed in 11 pairs, and increased in 6 pairs. We present new results pertaining to 12 phenanthrolines and 3 porphyrins. exception 3 For very large numbers used in a nontechnical sense, use a combination of numerals and words. 1 billion tons 180 million people 2 million pounds (not lb) 4.5 billion years $15 million (not 15 million dollars) ➤ When a sentence starts with a speciﬁc quantity, spell out the number as well as the unit of measure. Twelve species were evaluated in this study. Twenty slides of each blood sample were prepared. Fifteen milliliters of supernate was added to the reaction vessel. Twenty-ﬁve milliliters of acetone was added, and the mixture was centrifuged. However, if possible, recast the sentence. Acetone (25 mL) was added, and the mixture was centrifuged. A 25 mL portion of acetone was added, and the mixture was centrifuged. ➤ Even when a sentence starts with a spelled-out quantity, use numerals when appropriate in the rest of the sentence. Twenty-ﬁve milliliters of acetone and 5 mL of HCl were added. Three micrograms of sample was dissolved in 20 mL of acid. Fifty samples were collected, but only 22 were tested. Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 205 ➤ Use numerals for expressions used in a mathematical sense. The incidence of disease increased by a factor of 4. The yield of product was decreased by 6 orders of magnitude. The efﬁciency of the reaction was increased 2-fold. After 2 half-lives, the daughter product could be measured. The control group had 3 times the risk for colon cancer. The values are determined with 5 degrees of freedom. ➤ When the sufﬁx “fold” is used in a nonmathematical sense, spell out the accompanying number if it is less than 10. The purpose of this discussion is twofold. ➤ When the word “times” is used in a nonmathematical sense, spell out the accompanying number if it is less than 10. The beaker was rinsed four times. ➤ Use numerals in ratios. a ratio of 1:10 a ratio of 1/10 a 1:1 (v/v) mixture a 1/1 (v/v) mixture ➤ In dates, use numerals without ordinal endings. January 3, Jan 3 (not January 3rd, Jan 3rd) September 5, Sept 5 (not September 5th, Sept 5th) ➤ Use numerals for decades, and form their plurals by adding an “s”. Do not use apostrophes in any position. the 1960s (not the 1960’s, not the ’60s) values in the 90s (not the 90’s) She is in her 20s. (not her 20’s) ➤ Use numerals with a.m. and p.m. 12:15 a.m. 4:00 p.m. ➤ Spell out and hyphenate fractions whose terms are both less than 10. If one of the terms is 10 or greater, use a piece fraction. one-quarter of the experiments two-thirds of the results ¹⁄₂₀ of the subjects ¹⁄₁₂ of the volume 206 ➤ The ACS Style Guide ➤ Use numerals to label ﬁgures, tables, schemes, structures, charts, equations, and references. Number sequentially; do not skip numbers or number out of sequence. Use arabic numerals for references, but for the other items, the use of arabic and roman numerals varies among ACS publications. Consult a recent issue or author instructions to determine what system is preferred. ➤ In journal articles and book chapters, instead of repeating chemical names over and over, use numerals in boldface (not italic) type to identify chemical species. Use these identiﬁers only in text, not in article or chapter titles, and number consecutively. This paper describes the syntheses, structures, and stereodynamic behavior of the novel hexacoordinate silicon complexes 1–4. The cyclization of 1,3,5-hexatriene (6) to 1,3-cyclohexadiene (7) is predicted to proceed more rapidly in an electrostatic ﬁeld. Complexes 8–12, in the presence of monoamine oxidase, produce active catalysts for propylene polymerization. Primary amines 2–5, 7, and 9 gave the same Cotton effect signs, depending on the conﬁguration. Monomer III reacts with the initiator (I, Ar = 2,6-diisopropylphenyl) via a ringopening metathesis polymerization mechanism. ➤ Numerals may be used to name members of a series. Sample 1 contained a high level of contamination, but samples 2 and 3 were relatively pure. Methods 1 and 2 were used for water-soluble compounds, and methods 3 and 4 were used for oil-soluble compounds. ➤ When numerals are used as names and not enumerators, form their plurals by adding an apostrophe and “s” to avoid confusion with mathematical expressions and to make it clear that the “s” is not part of the name. The athlete received ﬁve 9’s from the judges. Boeing 747’s are among the largest airplanes. ➤ Arabic numerals in parentheses may be used to enumerate a list of phrases or sentences in text. Always use an opening and a closing parenthesis, not one alone. Some advantages of these materials are (1) their electrical properties after pyrolysis, (2) their ability to be modiﬁed chemically before pyrolysis, and (3) their abundance and low cost. The major conclusions are the following: (1) We have further validated the utility of molecular mechanical methods in simulating the kinetics of these reactions. Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 207 (2) A comparison of the calculated structures with available X-ray structures revealed satisfactory agreement. (3) The combined use of different theoretical approaches permitted characterization of the properties of a new isomer. ➤ Arabic numerals followed by periods or enclosed in parentheses may be used to enumerate a displayed list of sentences or to number paragraphs. Here are two acceptable ways to format a list. These results suggest the following: 1. Ketones are more acidic than esters. 2. Cyclic carboxylic acids are more acidic than their acyclic analogues. 3. Alkylation of the active methylene carbon reduces the acidity. These results suggest the following: (1) Ketones are more acidic than esters. (2) Cyclic carboxylic acids are more acidic than their acyclic analogues. (3) Alkylation of the active methylene carbon reduces the acidity. Style for Numbers ➤ For very large numbers with units of measure, use scientiﬁc notation or choose an appropriate multiplying preﬁx for the unit to avoid numbers of more than four digits. 1.2 × 106 s 3.0 × 104 kg 5.8 × 10–5 M or 58 µM 42.3 L (not 42,300 mL or 42 300 mL) exception 1 In tables, use the same unit and multiplying preﬁx for all entries in a column, even if some entries therefore require four or more digits. exception 2 Use the preferred unit of a discipline, even when the numbers require four or more digits: g/L kg/m3 GPa kPa MPa for mass density of ﬂuids for mass density of solids for modulus of elasticity for ﬂuid pressure for stress ➤ In four-digit numbers, use no commas or spaces. exception Spaces or commas are inserted in four-digit numbers when alignment is needed in a column containing numbers of ﬁve or more digits. ➤ When a long number cannot be written in scientiﬁc notation, the digits must be grouped. For grouping of digits in long numbers (ﬁve digits or greater), check the publication in which the manuscript will appear. Two styles are possible. 208 ➤ The ACS Style Guide style 1 In some publications, for numbers with ﬁve or more digits, the digits are grouped with commas placed between groups of three counting to the left of the decimal point. 4837 10,000 930,582 6,398,210 85,798.62578 style 2 In some publications (including ACS journals), for numbers with ﬁve or more digits, the digits are grouped with a thin space between groups of three, counting both to the left and to the right of the decimal point. 9319.4 74 183.0629 0.508 27 501 736.293 810 4 exceptions • U.S. monetary values are always written with commas: $5,000. • U.S. patent numbers are always written with commas: U.S. Patent 6,555,655. The patent numbers of other countries should be presented as on the original patent document. • Page numbers in reference citations are always printed solid: p 11597. ➤ Use the period as the decimal point, never a comma. ➤ Use numerals before and after a decimal point. 0.25 (not .25) 78.0 or 78 (not 78.) ➤ Use a decimal and a zero following a numeral only when such usage truly repre- sents the precision of the measurement: 27.0 °C and 27 °C are not interchangeable. ➤ Use decimals rather than fractions with units of time or measure, except when doing so would imply an unwarranted accuracy. 3.5 h (not 3½ h) 5.25 g (not 5¼ g) ➤ Standard deviation, standard error, or degree of accuracy can be given in two ways: • with only the deviation in the least signiﬁcant digit(s) placed in parentheses following the main number and closed up to it or • with all digits preceded by a ± and following the main number. Spaces are left on each side of the ±. Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 209 2.0089(1) means 2.0089 ± 0.0001 1.4793(23) means 1.4793 ± 0.0023 The shorter version is better in tables. Always specify which measure (e.g., standard deviation or standard error) of uncertainty is being used. ➤ When two numbered items are cited in narrative, use “and”. Figures 1 and 2 refs 23 and 24 compounds I and II ➤ Use a comma between two reference callouts in parentheses or as superscripts. Lewis (12, 13) found Lewis12,13 found When the reference numbers are on the line, the comma is followed by a space; when the numbers are superscripts, the comma is not followed by a space. ➤ Use an en dash in ranges or series of three or more numbered items, whether on the line or in a superscript. 43–49 325–372 2005–2008 Tables 1–4 temperatures of 100–125 °C refs 3–5 aliquots of 50–100 mL eqs 6–9 samples 5–10 past results (27–31) past results27–31 pp 165–172 exception 1 Do not use an en dash in expressions with the words “from … to” or “between … and”. from 20 to 80 (not from 20–80) between 50 and 100 mL (not between 50–100 mL) exception 2 When either one or both numbers are negative or include a symbol that modiﬁes the number, use the word “to” or “through”, not the en dash. –20 to +120 K –145 to –30 °C ≈50 to 60 10 to >600 mL <5 to 15 mg ➤ For ranges in scientiﬁc notation, retain all parts of all numbers or avoid ambiguity by use of parentheses or other enclosing marks. 9.2 × 10–3 to 12.6 × 10–3 or (9.2–12.6) × 10–3 (not 9.2 to 12.6 × 10–3) 210 ➤ The ACS Style Guide ➤ For very large numbers in ranges, retain all parts of all numbers. 26 million to 35 million ➤ Do not use e or E to mean “multiplied by the power of 10”. 3.7 × 105 (not 3.7e5, 3.7E+5) Mathematics Mathematical Concepts variable A variable is a quantity that changes in value, substance, or amount, such as V for volume, m for mass, and t for time. constant A constant is a quantity that has a ﬁxed value, such as h for the Planck constant and F for the Faraday constant. function The function f(x) = y represents a rule that assigns a unique value of y to every x. The argument of the function is x. operator An operator is a symbol, such as a function (d, derivative; ln, natural logarithm; and , the Hamiltonian operator) or an arithmetic sign (+, –, =, ÷, and ×), denoting an operation to be performed. physical quantity A physical quantity is a product of a numerical value (a pure number) and a unit. Physical quantities may be scalars or vectors, variables or constants. scalar A scalar is an ordinary number without direction, such as length, temperature, or mass. Any quantity that is not a vector quantity is a scalar quantity. vector A vector is a quantity with both magnitude and direction, such as j force or velocity. For the vector V = [a, b] (also denoted as V = [a, b]), a and b are the components of the vector. tensor A tensor represents a generalized vector with more than two components. matrix A matrix is represented by a rectangular array of elements; an array consists of rows and columns. The elements of matrix U are u11, u12, etc. u11  u1n  U =      un1  unn  Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 211 determinant The determinant of a matrix is a function that assigns a number to a matrix. For example, the determinant of the n × n matrix B is represented by b11  b1n det B =   bn1  bnn index An index is a subscript or superscript character in an element of a matrix, vector, or tensor; indices usually represent numbers. For example, i and j are indices in bij. Do not confuse abbreviations and mathematical symbols. An abbreviation is usually two or more letters; a mathematical symbol is generally only one letter, possibly with a subscript or superscript. An abbreviation is used in narrative text but seldom appears in equations; a mathematical symbol is preferred in equations and may also be used in text. For example, in text with no equations, PE for potential energy is acceptable, but in mathematical text and equations, Ep is preferred. Usage and Style for Symbols ➤ Deﬁne all symbols for mathematical constants, variables, and unknown quantities the ﬁrst time you use them in the text. If you use them in the abstract, deﬁne them there and then again at their ﬁrst appearance in text. Do not deﬁne standard mathematical constants such as π, i, and e. ➤ Form the plurals of mathematical symbols by adding an apostrophe and “s” if you cannot use a word such as “values” or “levels”. large r values is better than large r’s ➤ Do not use an equal sign as an abbreviation for the word “is” or the word “equals” in narrative text. PV = nRT, where P is pressure (not where P = pressure) when the temperature is 50 °C (not when the temperature = 50 °C) ➤ Do not use a plus sign as an abbreviation for the word “and” in narrative text. a mixture of A and B (not a mixture of A + B) ➤ Do not use an asterisk to indicate multiplication except in computer language expressions. 212 ➤ The ACS Style Guide Italic Type ➤ Use italic type for • • • • • • • variables: T for temperature, x for mole fraction, r for rate axes: the y axis planes: plane P components of vectors and tensors: a1 + b1 elements of determinants and matrices: gn constants: kB, the Boltzmann constant; g, the acceleration due to gravity functions that describe variables: f(x) ➤ Even when you use mathematical constants, variables, and unknown quantities in adjective combinations, retain the italic type. In this equation, Vi is the frequency of the ith mode. In eq 4, n is the number of extractions and M is the mass remaining after the nth extraction. ➤ Use italic type for two-letter variables deﬁning transport properties. Al Bi Co Da Eu Fo Fr Ga Gr Ha Kn Le Alfvén number Biot number Cowling number Damkohler number Euler number Fourier number Froude number Galileo number Grashof number Hartmann number Knudsen number Lewis number Ma Nu Pe Pr Ra Re Sc Sh Sr St We Wi Mach number Nusselt number Péclet number Prandtl number Rayleigh number Reynolds number Schmidt number Sherwood number Strouhal number Stanton number Weber number Weissenberg number Roman Type ➤ Use roman type for • numerals; • punctuation and enclosing marks such as square brackets, parentheses, and braces; • most operators; • units of measure and time: mg, milligram; K, kelvin; Pa, pascal; mmHg, millimeters of mercury; • nonmathematical quantities or symbols: R, radical in chemical nomenclature; S1, molecular state; s, atomic orbital; Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 213 • multiple-letter abbreviations for variables: IP, ionization potential; cmc, critical micelle concentration; • mathematical constants: e, the base of the natural logarithm, 2.71828… i, the imaginary number, (–1)1/2 π, 3.14159… • • • • transposes of matrices: AT (T is the transpose of matrix A); points and lines: point A, line AB; determinants: det A is the determinant of matrix A; and trigonometric and other functions: Ad Ai arg Bd cl Coker cos cosh cot coth csc csch det dim div erf erfc exp GL glb grad hom Im inf int ker adjoint Airy function argument bound closure cokernel cosine hyperbolic cosine cotangent hyperbolic cotangent cosecant hyperbolic cosecant determinant dimension divergence error function complement of error function exponential general linear greater lower bound gradient homology imaginary inferior interior kernel lim lim inf lim sup ln log Log lub max min mod P Re sec sech sign, sgn sin sinh SL sp Sp sup Sz(g) tan tanh tr wr limit limit inferior limit superior natural logarithm (base e) logarithm (base 10) principal logarithm least upper bound maximum minimum modulus property real secant hyperbolic secant sign sine hyperbolic sine special linear spin symplectic superior Suzuki group tangent hyperbolic tangent trace wreath Boldface Type ➤ Use boldface type for • • • • vectors; tensors; matrices; and multidimensional physical quantities: H, magnetic ﬁeld strength. 214 ➤ The ACS Style Guide Greek Letters Greek letters (lightface or boldface) can be used for variables, constants, and vectors and anywhere a Latin letter can be used. name Alpha Beta Gamma Delta Epsilon Zeta Eta Theta Iota Kappa Lambda Mu Nu Xi Omicron Pi Rho Sigma Tau Upsilon Phi Chi Psi Omega uppercase Α Β Γ ∆ Ε Ζ Η Θ Ι Κ Λ Μ Ν Ξ Ο Π Ρ Σ Τ Υ Φ Χ Ψ Ω lowercase α β γ δ, ∂ , ε ζ η θ, ϑ ι κ λ µ ν ξ ο π ρ σ τ υ ϕ, φ χ ψ ω Script and Open-Faced Letters ➤ Script () and open-faced (; also known as blackboard boldface) letters are available but should not be used routinely. For open-faced letters, only uppercase is available. Spacing ➤ Leave a space before and after functions set in roman type, unless the argument is enclosed in parentheses, brackets, or braces. log 2 –log x 4 sin θ tan2 y exp(–x) cosh(βe0φ) 4 tan(2y) erfc(y) Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 215 ➤ Leave a space before and after mathematical operators that function as verbs or conjunctions; that is, they have numbers on both sides or a symbol for a variable on one side and a number on the other. 20 ± 2% 3.24 ± 0.01 4 × 5 cm 8 × 10–4 k ≥ 420 s–1 p < 0.01 Tg = 176 °C n = 25 1 in. = 2.54 cm exception 1 Leave no space around mathematical operators in subscripts and superscripts. ∆Hn–1 Eλ>353 M(x+y)+ exception 2 Leave no space around a slash (a/b), a ratio colon (1:10), or a centered dot (PM·V). ➤ Leave no space between simple variables being multiplied: xy. Do not use a centered dot (·) or the times sign (×) with single-letter scalar variables. ➤ In multiplication involving the two-letter symbols for transport properties, use a space, enclose them in parentheses, or use the times sign. When superscripts or subscripts are present, the symbols can be closed up. Re Nu (Re)(Nu) Re × Nu RexNuy ➤ Use a space for simple multiplication of functions of the type f(x) (one-dimen- sional) or g(y, z) (multidimensional). Close up multipliers to such functions where applicable. You may also use additional enclosing marks instead of spaces. W = 2f(x) g(y, z) W = 2[f(x)][g(y, z)] ➤ When mathematical symbols are used as adjectives, that is, with one number that is not part of a mathematical operation, do not leave a space between the symbol and the number. a conversion of >50% –12 °C a probability of <0.01 25 g (±1%) at 400× magniﬁcation The level can vary from –15 to +25 m. 216 ➤ The ACS Style Guide Enclosing Marks ➤ Use enclosing marks (parentheses, brackets, and braces, also called fences) in accordance with the rules of mathematics. Enclose parentheses within square brackets, and square brackets within braces: {[( )]}. ➤ Use enclosing marks around arguments when necessary for clarity. sin(x + 1) sin[2π(x – y)/n] log[–V(r)/kT] ➤ Do not use square brackets, parentheses, or braces around the symbol for a quantity to make it represent any other quantity. incorrect where V is volume and (V) is volume at equilibrium correct where V is volume and Ve is volume at equilibrium Subscripts and Superscripts ➤ Use italic type for subscripts and superscripts that are themselves symbols for physical quantities or numbers. Use roman type for subscripts and superscripts that are abbreviations and not symbols. Cp for heat capacity at constant pressure CB for heat capacity of substance B Cg where g is gas Ei for energy of the ith level, where i is a number gn where n is normal µr where r is relative Ek where k is kinetic ξe where e is electric ➤ In most cases, staggered subscripts and superscripts are preferred. Exponents should follow subscripts. x12 T2m–1 Cx 1/2 ∆H1‡ Eads° exceptions λ∞+ σ+p B exptl 2 Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 217 ➤ Use a slash (/) in all subscript and superscript fractions, with no space on either side. x1/2 t1/2 M2/3 fa/b ➤ Leave no space around operators in subscripts and superscripts. M(2–n)+ ET+θ ➤ Leave no space around other expressions in subscripts and superscripts, unless confusion or misreading would result. βzero level Qn-Bu(750°C) E365nm ➤ The terms ea and exp a have the same meaning and can be interchanged. When an exponent to the base e is very long or complicated, replace the e with exp and place the exponent on line and in enclosing marks. Leave no space between exp and the opening enclosing mark. exp(∫y dt) (not e∫ydt) exp{½kT[Y(a + b) – Z]} (not e½kT[Y(a+b)–Z]) – ➤ In running text, do not use the radical sign (√ ) with long terms. Use enclos- ing marks around the term and a superscript 1/2, 1/3, 1/4 (etc.) for square, cube, fourth root (etc.), respectively. (x – y2)1/3 [sinh2 u + (cosh u – 1)2]1/2 Abbreviations and Symbols ➤ Certain abbreviations are used only in the context of mathematical equations. Deﬁne all of these the ﬁrst time they are used. lhs rhs ODE rms rmsd s.t. wrt, WRT left-hand side (of an equation) right-hand side (of an equation) ordinary differential equation root mean square root-mean-square deviation subject to with respect to ➤ Some standard usages and symbols for mathematical operations and constants need never be deﬁned. They include the following: e exp x, ex i ln x natural base (approximately 2.7183) exponential of x −1 natural logarithm of x 218 ➤ The ACS Style Guide log x loga x ≈  ∝, ∼ → ≡ ∞ Σ Π    ∇ ∇2 < ≤  > ≥  ≠ || ⊥ |a| a1/2, a a1/n, n a a, 〈a〉 ∆x ∂x dx f(x) y dx b logarithm to the base 10 of x logarithm to the base a of x approximately equal to asymptotically equal to proportional to approaches (tends to) identically equal to inﬁnity summation product union integral line integral around a closed path del (or nabla) operator, gradient Laplacian operator less than less than or equal to much less than greater than greater than or equal to much greater than not equal to parallel to perpendicular to absolute magnitude of a square root of a nth root of a mean value of a ﬁnite increment of x partial differential, inﬁnitesimal increment of x total differential of x function of x integral of y with respect to x ∫a y dx integral of y from x = a to x = b A A·B A × B, AB AB vector of magnitude A scalar product of A and B vector product of A and B length of line from A to B Equations Mathematical equations can be presented within running text or displayed on lines by themselves. Follow the guidelines for style and usage just described under “Usage and Style for Symbols” (starting on p 211). Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 219 ➤ Leave a space • before and after mathematical signs used as operators (=, ≠, ≡, ∼, ≈, ≅, >, <, +, –, ×, ÷, , , , , etc., but not slash (/), ratio colon, or centered dot), except when they appear in superscripts or subscripts • before trigonometric and other functions set in roman type • after trigonometric and other functions set in roman type when their arguments are not in enclosing marks • before and after derivatives: f(x) dx f(y) dy or x ∂x • between built-up (display) fractions as components of products: a c b d or write on one line and clarify with enclosing marks and no space: (a/b)(c/d) • between functions as components of products: W = 2f(x) g(y, z) ➤ Leave no space • between single-item variables being multiplied • in any part of a superscript or subscript, unless confusion or misreading would result • between any character and its own superscript, prime, or subscript • on either side of a colon used for a ratio • on either side of a centered dot • on either side of a slash (/) • after mathematical operators used as adjectives: –10 • after functions when the argument is in parentheses: tanh(λ/2) • between an opening parenthesis, bracket, or brace and the next character: (2x)y • between a closing parenthesis, bracket, or brace and the previous character: 2(xy) • between back-to-back parentheses, brackets, and braces, e.g., ]( • between nested parentheses, brackets, and braces, e.g., [( • in any part of limits to summations, products, and integrals • in any part of lower limits to min, max, lim, and inf ➤ Use or do not use spaces around ellipses, depending on the treatment of other items in the series. no spaces: anan+1an+2…an+36 spaces: an + an+1 + an+2 + … + an+36 space before: a, b, …, x 220 ➤ The ACS Style Guide ➤ Use enclosing marks in accordance with the rules of mathematics. If the slash (/) is used in division and if there is any doubt where the numerator ends or where the denominator starts, use enclosing marks for one or the other or both. (x + y)/(3x – y) (a/b)/c, or a/(b/c) x+y =z 2 x+y + 2a z but never a/b/c would be better as (x + y)/2 = z would be better as [(x + y)/z] + 2a ➤ If an equation is very short and will not be referred to again, you may run it into the text. A ﬂuid is said to be Newtonian when it obeys Newton’s law of viscosity, given by τ = ηγ, where τ is the shear stress, η is the ﬂuid dynamic constant, and γ is the shear rate. ➤ You may use mathematical expressions as part of a sentence when the subject, verb, and object are all part of the mathematical expression. When V = 12, eq 15 is valid. (V is the subject, = is the verb, and 12 is the object.) ➤ When an equation is too long to ﬁt on one line, break it after an operator that is not within an enclosing mark (parentheses, brackets, or braces) or break it between sets of enclosing marks. Do not break equations after integral, product, and summation signs; after trigonometric and other functions set in roman type; or before derivatives. ➤ Number displayed equations by using any consistent system of sequencing. 1, 2, 3, … 1a, 1b, 2, … I, II, III, … A, B, C, … A-1, A-2, A-3, … B.1, B.2, B.3, … C1, C2, C3, … ➤ Use equation identiﬁers in the proper sequence according to appearance in text. Do not skip numbers or letters in the sequence. ➤ Place identiﬁers in parentheses, ﬂush right on the same line as the equation. V = 64πkTγ2 exp(–κh) (3) Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 221 ➤ Do not use any closing punctuation on the line with displayed equations. ➤ When introducing a displayed equation, do not automatically use a colon; in most cases a colon is incorrect because the equation ﬁnishes a phrase or sentence. An ideal gas law analogy is πA = nRT If the principal radii are R1 and R2, then ∆ = R1 – R2 The area per adsorbed molecule can be calculated from a = NAΓS The attractive energy can be approximated by VA = Ar(12H)–1 The simplest method is to use a mapping potential of the form εm = (1 – λm)εA + λmεB Marshall developed an equation for rapid coagulation: n = 1 + SπDrt ➤ Following a displayed equation that is part of a sentence, punctuate the text as if it were a continuation of a sentence including the equation but do not punctuate at the end of the equation. Note the absence of a comma at the end of the equation in the example. Punctuation that would normally be present at the end of an equation in text is absent but implicit at the end of a displayed equation. The capillary pressure P depends signiﬁcantly on the wetting contact angle according to P = 2γ cos(θ/r) where γ is the surface tension, θ is the wetting contact angle, and r is the radius of the capillary. ➤ To cite an equation in text, use the abbreviation “eq” if it is not the ﬁrst word of the sentence. Spell out “equation” when it is the ﬁrst word of a sentence or when it is not accompanied by a number. The plural of “eq” is “eqs”. The number of independent points can be calculated from eq 3. The number of independent points can be calculated from eqs 3 and 4. Equation 1 is not accurate for distances greater than 10 µm. Equations 1 and 2 are not accurate for distances greater than 10 µm. 222 ➤ The ACS Style Guide ➤ Some notations differ in text and in display: In display N In text ∑ ΣNi=1 or Σi=1N ∏ Πnk=2 or Πk=2n lim limi=1 max maxj=2 min minj=k,n i =1 n k =2 i =1 j =2 j =k ,n Ratio and Mixture Notation ➤ Use either a colon or a slash (/) to represent a ratio, but not an en dash. Use either a slash or an en dash between components of a mixture, but not a colon. dissolved in 5:1 glycerin/water dissolved in 5:1 glycerin–water the metal/ligand (1:1) reaction mixture the metal–ligand (1:1) reaction mixture the metal–ligand (1/1) reaction mixture the methane/oxygen/argon (1/50/450) matrix the methane/oxygen/argon (1:50:450) matrix Set Notation The following symbols are used in set notation. Leave a space before and after all operators, but not before and after braces. A = {a, b} set A; A is italic; braces are used AB union of sets A and B AB intersection of sets A and B AB A is a member (element) of B AB A is not a member (element) of B AB A is contained in B AB A is not contained in B AB A contains B AB A does not contain B ∀A for all (every) A ∃ there exists ∋ such that ∴ therefore Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 223 Geometric Notation ➤ Leave no spaces around geometric notation. Use italic type for planes and axes and roman type for points and lines. X⊥Y X||Y AB AB X is perpendicular to Y X is parallel to Y the angle between A and B length of line from A to B Statistics Certain statistical symbols are standard. CV df, DF f F n, N p, P r R RSD σ, SD Σ s2 SE SEM t x coefﬁcient of variation degrees of freedom frequency variance ratio total number of individuals or random variables probability correlation coefﬁcient regression coefﬁcient relative standard deviation standard deviation summation sample variance standard error standard error of the mean Student distribution (the Student t test) arithmetic mean A common statistical measurement is the Student t test or Student’s t test. Student was the pseudonym of W. Gossett, an eminent mathematician. Units of Measure ➤ Where possible, use metric and SI units (discussed in Appendix 11-1) in all technical documents. The following conventions apply to all units of measure: • Abbreviate units of measure when they accompany numbers. • Leave a space between a number and its unit of measure. • Do not use a period after an abbreviated unit of measure (exception: in. for inch). 224 ➤ The ACS Style Guide • Do not deﬁne units of measure. 500 mL 3 min 4Å 9 V/s 9 V s–1 9 V·s–1 200 mV 4.14 × 10–9 m2/(V s) 2.6 × 104 J 3 min interval 2 µm droplet 500 mL ﬂask exception Do not leave a space between a number and the percent, angular degree, angular minute, or angular second symbols. 50% 90° 75′ 18″ ➤ Use °C with a space after a number, but no space between the degree symbol and the capital C: 15 °C. ➤ Do not add an “s” to make the plural of any abbreviated units of measure. The abbreviations are used as both singular and plural. 50 mg (not 50 mgs) 3 mol (not 3 mols) ➤ Write abbreviated compound units with a centered dot or a space between the units to indicate multiplication and a slash (/) or negative exponent for division. Enclose compound units following a slash in parentheses. Usage should be consistent within a paper. watt per meter-kelvin is W·m–1·K–1 or W/(m·K) or W m–1 K–1 or W (m K)–1 or W/(m K) cubic decimeter per mole-second is dm3·mol–1·s–1 or dm3/(mol·s) or dm3 mol–1 s–1 or dm3 (mol s)–1 or dm3/(mol s) joule per mole-kelvin is J·mol–1·K–1 or J/(mol·K) or J mol–1 K–1 or J (mol K)–1 or J/(mol K) Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 225 ➤ Spell out units of measure that do not follow a number. Do not capitalize them unless they are at the beginning of a sentence or in a title. several milligrams (not several mg) a few milliliters (not a few mL) degrees Celsius reciprocal seconds milligrams per kilogram volts per square meter exception 1 Abbreviate units of measure in parentheses after the deﬁnitions of variables directly following an equation. L = D/PO where L is the distance between particles (cm), D is the particle density (g/cm3), and PO is the partial pressure of oxygen (kPa). exception 2 Certain units of measure have no abbreviations: bar, darcy, einstein, erg, faraday, and langmuir. The symbol for the unit torr is Torr. The unit rad is abbreviated rd; the unit radian is abbreviated rad. exception 3 In column headings of tables and in axis labels of ﬁgures, abbreviate units of measure, even without numbers. ➤ Add an “s” to form the plural of spelled-out units: milligrams, poises, kelvins, amperes, watts, newtons, and so on. exceptions bar, hertz, lux, stokes, siemens, and torr remain unchanged; darcy becomes darcies; henry becomes henries. ➤ Do not capitalize surnames that are used as units of measure. ampere angstrom coulomb curie dalton darcy debye einstein erg faraday franklin gauss gilbert gray hartree henry hertz joule kelvin langmuir newton ohm pascal poise siemens sievert stokes tesla watt weber Celsius and Fahrenheit are always capitalized. They are not themselves units; they are the names of temperature scales. ➤ Do not use a slash (/) in spelled-out units of measure. Use the word “per”. Results are reported in meters per second. The ﬂuid density is given in kilograms per cubic meter. 226 ➤ The ACS Style Guide ➤ Do not mix abbreviations and spelled-out units within units of measure. newtons per meter (not N per meter) 100 F/m (not 100 farad/m) exception in more complex situations 50 mL of water and 20 mg of NaOH per gram of compound ➤ Use a slash (/), not the word “per”, before the abbreviation for a unit in com- plex expressions. 50 µg of peptide/mL 25 mg of drug/kg of body weight ➤ When the ﬁrst part of a unit of measure is a word that is not itself a unit of measure, use a slash (/) before the ﬁnal abbreviated unit. 10 counts/s 12 domains/cm3 2 × 103 ions/min 125 conversions/mm2 ➤ When the last part of a unit of measure is a word that is not itself a unit of meas- ure, use either a slash (/) or the word “per” before the word that is not a unit. 0.8 keV/channel 0.8 keV per channel 7 µB/boron 7 µB per boron ➤ Leave no space between the multiplying preﬁx and the unit, whether abbrevi- ated or spelled out. kilojoule or kJ milligram or mg microampere or µA ➤ Use only one multiplicative preﬁx per unit. nm (not mµm) ➤ In ranges and series, retain only the ﬁnal unit of measure. 10–12 mg 5, 10, and 20 kV 60–90° between 25 and 50 mL from 10 to 15 min Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 227 ➤ Do not use the degree symbol with kelvin: 115 K. ➤ In titles and headings, do not capitalize abbreviated units of measure that are ordinarily lowercase. Analysis of 2 mg Samples A 50 kDa Protein To Modulate Guanine Nucleotide Binding ➤➤➤➤➤ APPENDIX 11-1 The International System of Units (SI) Before the 1960s, four systems of units were commonly used in the scientiﬁc literature: the English system (centuries old, using yard and pound), the metric system (dating from the 18th century, using meter and kilogram as standard units), the CGS system (based on the metric system, using centimeter, gram, and second as base units), and the MKSA or Giorgi system (using meter, kilogram, second, and ampere as base units). The International System of Units (SI, Système International d’Unités) is the most recent effort to develop a coherent system of units. It is coherent because there is only one unit for each base physical quantity, and units for all other quantities are derived from these base units by simple equations. It has been adopted as a universal system to simplify communication of numerical data and to restrict proliferation of systems. SI units are used by the National Institute of Standards and Technology (NIST). More information on SI can be found at http://www.physics.nist.gov/cuu/index.html. The SI is constructed from seven base units for independent quantities (ampere, candela, kelvin, kilogram, meter, mole, and second) plus two supplementary units for plane and solid angles (radian and steradian). Most physicochemical measurements can be expressed in terms of these units. Certain units not part of the SI are so widely used that it is impractical to abandon them (e.g., liter, minute, and hour) or are so well established that the International Committee on Weights and Measures has authorized their continued use (e.g., bar, curie, and angstrom). In addition, quantities that are expressed in terms of the fundamental constants of nature, such as elementary charge, proton mass, Bohr magneton, speed of light, and Planck constant, are also acceptable. However, broad terms such as “atomic units” are not acceptable, although atomic mass unit, u, is acceptable and relevant to chemistry. Follow all usage conventions given for units of measure. Use the abbreviations for SI units with capital and lowercase letters exactly as they appear in Tables 11A-1 to 11A-6. 228 Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 229 Table 11A-1. SI Units Name Symbol Physical Quantity Base units ampere candela kelvin kilogram meter mole second A cd K kg m mol s electric current luminous intensity thermodynamic temperature mass length amount of substance time Supplementary units radian steradian rad sr plane angle solid angle Table 11A-2. Multiplying Prefixes Factor Preﬁx Symbol 10–24 10–21 10–18 10–15 10–12 10–9 10–6 10–3 10–2 10–1 yocto zepto atto femto pico nano micro milli centi deci y z a f p n µ m c d Factor Preﬁx Symbol 101 102 103 106 109 1012 1015 1018 1021 1024 deka hecto kilo mega giga tera peta exa zetta yotta da h k M G T P E Z Y Note: Any of these prefixes may be combined with any of the symbols permitted within the SI. Thus, kPa and GPa will both be common combinations in measurements of pressure, as will mL and cm for measurements of volume and length, respectively. As a general rule, however, the prefix chosen should be 10 raised to that multiple of 3 that will bring the numerical value of the quantity to a positive value less than 1000. Table 11A-3. SI-Derived Units Name becquerel coulomb farad gray Symbol Bq C F Gy henry hertz joule lumen lux newton ohm pascal siemens sievert tesla volt H Hz J lm lx N Ω Pa S Sv T V watt weber W Wb Quantity activity (of a radionuclide) quantity of electricity, electric charge capacitance absorbed dose, kerma, specific energy imparted inductance frequency energy, work, quantity of heat luminous flux illuminance force electric resistance pressure, stress conductance dose equivalent magnetic flux density electric potential, potential difference, electromotive force power, radiant flux magnetic flux In Terms of In Terms of Other Units SI Base Units — s–1 — s·A C/V m–2·kg–1·s4·A2 J/kg m2·s–2 Wb/A — N·m cd·sr lm/m2 — V/A N/m2 A/V J/kg Wb/m2 W/A m2·kg·s–2·A–2 s–1 m2·kg·s–2 m2·m–2·cd = cd m2·m–4·cd = m–2·cd m·kg·s–2 m2·kg·s–3·A–2 m–1·kg·s–2 m–2·kg–1·s3·A2 m2·s–2 kg·s–2·A–1 m2·kg·s–3·A–1 J/s V·s m2·kg·s–3 m2·kg·s–2·A–1 230 ➤ The ACS Style Guide Table 11A-4. SI-Derived Compound Units Name ampere per meter ampere per square meter candela per square meter coulomb per cubic meter coulomb per kilogram coulomb per square meter cubic meter cubic meter per kilogram farad per meter henry per meter joule per cubic meter joule per kelvin joule per kilogram joule per kilogram kelvin joule per mole joule per mole kelvin kilogram per cubic meter meter per second meter per second squared mole per cubic metera newton-meter newton per meter pascal second radian per second radian per second squared reciprocal meter reciprocal second square meter square meter per second volt per meter watt per meter kelvin watt per square meter watt per square meter steradian watt per steradian a Symbol A/m A/m2 cd/m2 C/m3 C/kg C/m2 m3 m3/kg F/m H/m J/m3 J/K J/kg J/(kg K) Quantity magnetic field strength current density luminance electric charge density exposure (X-rays and γ rays) electric flux density volume specific volume permittivity permeability energy density heat capacity, entropy specific energy specific heat capacity, specific entropy J/mol molar energy J/(mol K) molar entropy, molar heat capacity kg/m3 density, mass density m/s speed, velocity m/s2 acceleration mol/m3 concentration (amount of substance per volume) N·m moment of force N/m surface tension Pa·s dynamic viscosity rad/s angular velocity rad/s2 angular acceleration m–1 wavenumber s–1 frequency m2 area m2/s kinematic viscosity V/m electric field strength W/(m K) thermal conductivity W/m2 heat flux density, irradiance W/(m2 sr) radiance W/sr radiant intensity In Terms of Other Units — — — m–3·s·A — m–2·s·A — — m–3·kg–1·s4·A2 m·kg·s–2·A–2 m–1·kg·s–2 m2·kg·s–2·K–1 m2·s–2 m2·s–2·K–1 m2·kg·s–2·mol–1 m2·kg·s–2·K–1·mol–1 — — — — m2·kg·s–2 kg·s–2 m–1·kg·s–1 — — — — — — m·kg·s–3·A–1 m·kg·s–3·K–1 kg·s–3 — — Liter (L) is a special name for cubic decimeter. The symbol M is not an SI unit, but expressions such as 0.1 M, meaning a solution with concentration of 0.1 mol/L, are acceptable. Chapter 11: Numbers, Mathematics, and Units of Measure ➤ 231 Table 11A-5. Other Units Name Symbol angstrom Å bar bar barn b bohr b, a0 curiea Ci dalton Da darcyb darcy day day c D debye degree ° degree Celsiusd °C dynee dyn einsteinf einstein electronvoltg eV ergh erg faraday faraday fermi f franklin Fr galileo Gal gauss G i gilbert Gi hartree hartree, Eh hectare ha hour h liter L metric ton t minute min minute ′ parsec pc poisej P rad rad, rdk roentgen R roentgen equivalent rem manl ″ second St stokesm svedberg Sv unified atomic mass u unit n a Quantity distance pressure area, cross section length activity atomic mass permeability time electric dipole moment plane angle temperature force light energy — energy or work electric charge length electric charge acceleration magnetic induction magnetomotive force energy area time volume mass time plane angle length dynamic viscosity absorbed dose exposure weighted absorbed dose plane angle kinematic viscosity time — Value in SI Units 1 Å = 10–10 m = 0.1 nm 1 bar = 105 Pa = 100 kPa = 0.1 MPa 1 b = 10–28 m2 = 100 fm2 1 b ≈ 5.291 77 × 10–11 m 1 Ci = 3.7 × 1010 Bq 1 Da = 1.660 540 × 10–27 kg — 1 day = 24 h = 86 400 s — 1° = (π/180) rad — — — 1 eV = 1.602 19 × 10–19 J — 1 faraday = 96 485.31 C 1 f = 10–15 m 1 Fr = 3.335 64 × 10–10 C 1 Gal = 10–2 m s–2 1 G = 10–4 Wb/m2 — 1 hartree = 4.359 75 × 10–18 J 1 ha = 1 hm2 = 104 m2 1 h = 60 min = 3600 s 1 L = 1 dm3 = 10–3 m3 1 t = 103 kg 1 min = 60 s 1′ = (1/60)° = (π/10 800) rad 1 pc ≈ 3.085 68 × 1016 m — 1 rad = 0.01 Gy = 1 cGy = 100 erg·g–1 1 R = 2.58 × 10–4 C·kg–1 1 rem = 0.01 Sv 1″ + (1/60)′ = (π/648 000) rad — 1 Sv = 10–13 s 1 u = 1.660 540 × 10–27 kg 1 Ci = 2.2 × 1012 disintegrations per minute. 1 darcy is the permeation achieved by the passage of 1 mL of fluid of 1 cP viscosity flowing in 1 s under a pressure of 1 atm (101 kPa) through a porous medium that has a cross-sectional area of 1 cm 2 and a length of 1 cm. c 1 D = 10–18 Fr cm. d Temperature intervals in kelvins and degrees Celsius are identical; however, temperature in kelvins equals temperature in degrees Celsius plus 273.15. e 1 dyn is equal to the force that imparts an acceleration of 1 cm/s2 to a 1 g mass. f 1 einstein equals Avogadro’s number times the energy of one photon of light at the frequency in question. g The electronvolt is the kinetic energy acquired by an electron in passing through a potential difference of 1 V in vacuum. h 1 erg is the work done by a 1 dyn force when the point at which the force is applied is displaced by 1 cm in the direction of the force. i 1 Gi is the magnetomotive force of a closed loop of one turn in which there is a current of (1/4 π) × 10 A. j 1 P is the dynamic viscosity of a fluid in which there is a tangential force of 1 dyn/cm 2 resisting the flow of two parallel fluid layers past each other when their differential velocity is 1 cm/s per centimeter of separation. k When there is a possibility of confusion with the symbol for radian, rd may be used as the symbol for rad. l 1 rem has the same biological effect as 1 rad of X-rays. m 1 St is the kinematic viscosity of a fluid with a dynamic viscosity of 1 P and a density of 1 g/cm 3. n The unified atomic mass unit is equal to 1/12 of the mass of an atom of the nuclide 12C. b 232 ➤ The ACS Style Guide Table 11A-6. Non-SI Units That Are Discouraged Discouraged Unit calorie (thermochemical) conventional millimeter of mercury grad kilogram-force metric carat metric horsepower mho micron standard atmosphere technical atmosphere torr Value in SI Units 4.184 J 133.322 Pa 2π/400 rad 9.806 65 N 0.2 g 735.499 W 1S 1 µm 101.325 kPa 98.066 5 kPa 133.322 Pa ➤➤➤➤➤ CHAPTER 12 Names and Numbers for Chemical Compounds T he use of proper chemical nomenclature is essential for effective scientiﬁc communication. More than one million new substances are reported each year, each of which must be identiﬁed clearly, unambiguously, and completely in the primary literature. Chemical compounds are named according to the rules established by the International Union of Pure and Applied Chemistry (IUPAC), the International Union of Biochemistry and Molecular Biology (IUBMB) [formerly the International Union of Biochemistry (IUB)], the Chemical Abstracts Service (CAS), the Committee on Nomenclature, Terminology, and Symbols of the American Chemical Society, and other authorities as appropriate. For more information on naming chemical compounds, refer to the bibliography in Chapter 18. This chapter gives the editorial conventions and style points for chemical compound names. Components of Chemical Names The names of chemical compounds may consist of one or more words, and they may include locants, descriptors, and syllabic portions. Locants and descriptors can be numerals, element symbols, small capital letters, Greek letters, Latin letters, italic words and letters, and combinations of these. Treat the word or syllabic portions of chemical names just like other common nouns: use roman type, keep them lowercase in text, capitalize them at the beginnings of sentences and in titles, and hyphenate them only when they do not ﬁt completely on one line. Copyright 2006 American Chemical Society 233 234 ➤ The ACS Style Guide ➤➤➤➤➤ Box 12-1. Correct Forms for Alcohols Correct forms 1-butanol, butyl alcohol 2-butanol, sec-butyl alcohol 2-methyl-1-propanol, isobutyl alcohol 2-methyl-2-propanol, tert-butyl alcohol 1-propanol, propyl alcohol 2-propanol, isopropyl alcohol Incorrect forms isobutanol isopropanol any combination of sec or tert with the words butanol or propanol Locants and Descriptors ➤ Numerals used as locants can occur at the beginning of or within a chemical name. They are set off with hyphens. (See Box 12-1.) 6-aminobenzothiazole di-2-propenylcyanamide 4a,8a-dihydronaphthalene 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 6-hydroxy-2-naphthalenesulfonic acid 3′-methylphthalanilic acid ➤ Use italic type for chemical element symbols that denote attachment to an atom or a site of ligation. B,B′-di-3-pinanyldiborane bis[(ethylthio)acetato-O,S]platinum glycinato-N N-acetyl group N-ethylaniline N,N ′-bis(3-aminopropyl)-1,4-butanediamine O,O,S-triethyl phosphorodithioate P-phenylphosphinimidic acid S-methyl benzenethiosulfonate ➤ When element symbols are used with a type of reaction as a noun or adjective, use roman type for the symbol and hyphenate it to the word that follows it. N-acetylated N-acetylation N-oxidation N-oxidized O-substituted O-substitution S-methylated S-methylation Chapter 12: Names and Numbers for Chemical Compounds ➤ 235 ➤ Use italic type for the capital H that denotes indicated or added hydrogen. phosphinin-2(1H)-one 2H-pyran-3(4H)-thione 1H-1,3-diazepine 3H-ﬂuorene 2H-indene ➤ Use Greek letters, not the spelled-out forms, in chemical names to denote posi- tion or stereochemistry. Use a hyphen to separate them from the chemical name. α-amino acid (not alpha amino acid) β-naphthol (not beta naphthol) 5α,10β,15α,20α-tetraphenylporphyrin Use the Greek letters eta (η) to indicate hapticity and kappa (κ) to designate the ligating atom in complicated formulas. bis(η6-benzene)-chromium bis(η-cyclopentadienyl) iron [2-(diphenylphosphino-κP)phenyl-κC1]hydrido(triphenylphosphine-κP)nickel(II) N,N ′-bis(2-amino-κN-ethyl)ethane-1,2-diamine-κN]chloroplatinum(II) ➤ Use italic type for positional, stereochemical, conﬁgurational, and descriptive structural preﬁxes when they appear with the chemical name or formula. Use a hyphen to separate them from the chemical name. Accepted preﬁxes include the following: abeo ac altro amphi anti antiprismo ar arachno as asym c catena cis cisoid closo cyclo d dodecahedro E endo erythro exo facgem hexahedro hexaprismo hypho icosahedro klado l m M mer meso n nido o octahedro p P pentaprismo quadro r R R∗ rel retro ribo s S S∗ sec sn sym syn t tert tetrahedro threo trans transoid triangulo triprismo uns vic xylo Z ➤ Do not capitalize preﬁxes that are shown here as lowercase, even at the begin- ning of a sentence or in a title (see Tables 12-1 and 12-2), and never use lower- 236 ➤ The ACS Style Guide case for those that are written in capital letters. Enclose the preﬁxes E, R, R∗, S, S∗, and Z in parentheses. anti-bicyclo[3.2.1]octan-8-amine ar-chlorotoluene as-trichlorobenzene catena-triphosphoric acid cis-diamminedichloroplatinum cis-[PtCl2(NH3)2] cyclo-hexasulfur, c-S6 (E,E)-2,4-hexadienoic acid (E,Z)-1,3-di-1-propenylnaphthalene erythro-2,3-dibromosuccinic acid exo-chloro-p-menthane m-ethylpropylbenzene meso-tartaric acid o-dibromobenzene p-aminoacetanilide s-triazine (S)-2,3-dihydroxypropanoic acid 5-sec-butylnonane sym-dibromoethane tert-pentyl bromide, t-C5H11Br threo-2,3-dihydroxy-1,4dimercaptobutane trans-2,3-dimethylacrylic acid uns-dichloroacetone vic-triazine ➤ Use small capital letters d and l to indicate absolute conﬁguration with amino acids and carbohydrates. 2-(diﬂuoromethyl)-dl-ornithine l-galactosamine 2-O-β-d-glucopyranosyl-α-d-glucose ➤ Use plus and minus signs enclosed in parentheses as stereochemical descriptors. (±)-2-allylcyclohexanone (+)-dihydrocinchonine (–)-3-(3,4-dihydroxyphenyl)-l-alanine ➤ When the structural preﬁxes cyclo, iso, neo, and spiro are integral parts of chemical names, close them up to the rest of the name (without hyphens) and do not italicize them. cyclohexane isopropyl alcohol neopentane However, italicize and hyphenate cyclo as a nonintegral structural descriptor. cyclo-octasulfur cyclo-triphosphoric acid ➤ Use numerals separated by periods within square brackets in names of bridged and spiro alicyclic compounds. bicyclo[3.2.0]heptane bicyclo[4.4.0]decane 1-methylspiro[3.5]non-5-ene spiro[4.5]decane Chapter 12: Names and Numbers for Chemical Compounds ➤ 237 Table 12-1. Examples of Multiword Chemical Names In Text At Beginning of Sentence In Titles and Headings Acids benzoic acid ethanethioic S-acid hydrochloric acid Benzoic acid Ethanethioic S-acid Hydrochloric acid Benzoic Acid Ethanethioic S-Acid Hydrochloric Acid Alcohols ethyl alcohol ethylene glycol Ethyl alcohol Ethylene glycol Ethyl Alcohol Ethylene Glycol Ketones di-2-naphthyl ketone methyl phenyl ketone Di-2-naphthyl ketone Methyl phenyl ketone Di-2-naphthyl Ketone Methyl Phenyl Ketone Ethers di-sec-butyl ether methyl propyl ether Di-sec-butyl ether Methyl propyl ether Di-sec-butyl Ether Methyl Propyl Ether Anhydrides acetic anhydride phthalic anhydride Acetic anhydride Phthalic anhydride Acetic Anhydride Phthalic Anhydride Esters methyl acetate phenyl thiocyanate propyl benzoate Methyl acetate Phenyl thiocyanate Propyl benzoate Methyl Acetate Phenyl Thiocyanate Propyl Benzoate Polymer Names 1,2-polybutadiene poly(butyl methacrylate) poly(ethylene glycol) poly(N,N-dimethylacrylamide) 1,2-Polybutadiene Poly(butyl methacrylate) Poly(ethylene glycol) Poly(N,N-dimethylacrylamide) 1,2-Polybutadiene Poly(butyl methacrylate) Poly(ethylene glycol) Poly(N,N-dimethylacrylamide) Other Organic Compounds aniline hydrochloride benzyl hydroperoxide butyl chloride dicyclohexyl peroxide diethyl sulfide methyl iodide 2-naphthoyl bromide sodium S-phenyl thiosulfite tert-butyl fluoride Aniline hydrochloride Benzyl hydroperoxide Butyl chloride Dicyclohexyl peroxide Diethyl sulfide Methyl iodide 2-Naphthoyl bromide Sodium S-phenyl thiosulfite tert-Butyl fluoride Aniline Hydrochloride Benzyl Hydroperoxide Butyl Chloride Dicyclohexyl Peroxide Diethyl Sulfide Methyl Iodide 2-Naphthoyl Bromide Sodium S-Phenyl Thiosulfite tert-Butyl Fluoride Inorganic and Coordination Compounds ammonium hydroxide Ammonium hydroxide bis(diethyl phosphato)zinc Bis(diethyl phosphato)zinc calcium sulfate Calcium sulfate (dimethyl sulfoxide)-cadmium (Dimethyl sulfoxide)-cadmium sulfate sulfate magnesium oxide Magnesium oxide sodium cyanide Sodium cyanide sulfur dioxide Sulfur dioxide Ammonium Hydroxide Bis(diethyl phosphato)zinc Calcium Sulfate (Dimethyl sulfoxide)-cadmium Sulfate Magnesium Oxide Sodium Cyanide Sulfur Dioxide 238 ➤ The ACS Style Guide Table 12-2. Locants and Descriptors in Chemical Names In Text Numeral Locants adenosine 5′-triphosphate 1,3-bis(bromomethyl)benzene 2-benzoylbenzoic acid 1-bromo-3-chloropropane 2-(2-chloroethyl)pentanoic acid 7-(4-chlorophenyl)-1naphthol 1,2-dicyanobutane 4a,8a-dihydronaphthalene Element Symbol Locants (2,3-butanedione dioximatoO,O′)copper N-ethylaniline N,2-dihydroxybenzamide N,N′-dimethylurea 3H-fluorene O,S,S-triethyl phosphorodithioate S-methyl benzenethiosulfonate At Beginning of Sentence In Titles and Headings Adenosine 5′-triphosphate Adenosine 5′-Triphosphate 1,3-Bis(bromomethyl)-benzene 1,3-Bis(bromomethyl)-benzene 2-Benzoylbenzoic acid 1-Bromo-3-chloropropane 2-(2-Chloroethyl)pentanoic acid 7-(4-Chlorophenyl)-1-naphthol 2-Benzoylbenzoic Acid 1-Bromo-3-chloropropane 2-(2-Chloroethyl)pentanoic Acid 7-(4-Chlorophenyl)-1-naphthol 1,2-Dicyanobutane 4a,8a-Dihydronaphthalene 1,2-Dicyanobutane 4a,8a-Dihydronaphthalene (2,3-Butanedione dioximatoO,O′)copper N-Ethylaniline N,2-Dihydroxybenzamide N,N′-Dimethylurea 3H-Fluorene O,S,S-Triethyl phosphorodithioate S-Methyl benzenethiosulfonate (2,3-Butanedione dioximatoO,O′)copper N-Ethylaniline N,2-Dihydroxybenzamide N,N′-Dimethylurea 3H-Fluorene O,S,S-Triethyl Phosphorodithioate S-Methyl Benzenethiosulfonate Greek Letter Locants and Descriptors α-hydroxy-β-aminobutyric α-Hydroxy-β-aminobutyric acid acid 17α-hydroxy-5β-pregnane 17α-Hydroxy-5β-pregnane 1α-hydroxycholecalciferol 1α-Hydroxycholecalciferol α-methylbenzeneacetic acid α-Methylbenzeneacetic acid α1-sitosterol α1-Sitosterol β-chloro-1β-Chloro-1naphthalenebutanol naphthalenebutanol β,4-dichlorocyclohexaneβ,4-Dichlorocyclohexanepropionic acid propionic acid β-endorphin β-Endorphin ω,ω′-dibromopolybutadiene ω,ω′-Dibromopolybutadiene tris(β-chloroethyl)amine Tris(β-chloroethyl)amine β,4-Dichlorocyclohexanepropionic Acid β-Endorphin ω,ω′-Dibromopolybutadiene Tris(β-chloroethyl)amine Small Capital Letter Descriptors β-D-arabinose β-D-Arabinose D-1,2,4-butanetriol D-1,2,4-Butanetriol D-serine D-Serine DL-alanine DL-Alanine DS-threonine DS-Threonine L-methionine L-Methionine β-D-Arabinose D-1,2,4-Butanetriol D-Serine DL-Alanine DS-Threonine L-Methionine Positional and Structural Descriptors 7-bromo-p-cymene 7-Bromo-p-cymene 4-chloro-m-cresol 4-Chloro-m-cresol m-hydroxybenzyl alcohol m-Hydroxybenzyl alcohol n-butyl iodide n-Butyl iodide α-Hydroxy-β-aminobutyric Acid 17α-Hydroxy-5β-pregnane 1α-Hydroxycholecalciferol α-Methylbenzeneacetic Acid α1-Sitosterol β-Chloro-1-naphthalenebutanol 7-Bromo-p-cymene 4-Chloro-m-cresol m-Hydroxybenzyl Alcohol n-Butyl Iodide Continued on next page Chapter 12: Names and Numbers for Chemical Compounds ➤ 239 Table 12-2. Locants and Descriptors in Chemical Names—Continued In Text At Beginning of Sentence In Titles and Headings Positional and Structural Descriptors—Continued 2-(o-chlorophenyl)-1naphthol o-dibromobenzene p-benzenediacetic acid p-tert-butylphenol s-triazine sec-butyl alcohol sym-dibromoethane tert-pentyl isovalerate 1-(trans-1-propenyl)-3-(cis-1propenyl)naphthalene Stereochemical Descriptors anti-bicyclo[3.2.1]octan-8amine cis-1,2-dichloroethene d-camphor dl-2-aminopropanoic acid (E)-diphenyldiazene endo-2-chlorobicyclo[2.2.1]heptane (+)-erythro-2-amino-3methylpentanoic acid erythro-β-hydroxyaspartic acid exo-bicyclo[2.2.2]oct-5-en2-ol exo-5,6-dimethyl-endobicyclo[2.2.2]octan-2-ol L-threo-2,3-dichlorobutyric acid meso-tartaric acid (1R*,3S*)-1-bromo-3chlorocyclohexane rel-(1R,3R)-1-bromo-3chlorocyclohexane (S)-2,3-dihydroxypropanoic acid sn-glycerol 1-(dihydrogen phosphate) syn-7-methylbicyclo[2.2.1]heptene trans-cisoid-transperhydrophenanthrene (Z)-5-chloro-4-pentenoic acid (1Z,4E)-1,2,4,5-tetrachloro1,4-pentadiene 2-(o-Chlorophenyl)-1-naphthol 2-(o-Chlorophenyl)-1-naphthol o-Dibromobenzene p-Benzenediacetic acid p-tert-Butylphenol s-Triazine sec-Butyl alcohol sym-Dibromoethane tert-Pentyl isovalerate 1-(trans-1-Propenyl)-3-(cis-1propenyl)naphthalene o-Dibromobenzene p-Benzenediacetic Acid p-tert-Butylphenol s-Triazine sec-Butyl Alcohol sym-Dibromoethane tert-Pentyl Isovalerate 1-(trans-1-Propenyl)-3-(cis-1propenyl)naphthalene anti-Bicyclo[3.2.1]octan-8amine cis-1,2-Dichloroethene d-Camphor dl-2-Aminopropanoic acid (E)-Diphenyldiazene endo-2-Chlorobicyclo[2.2.1]heptane (+)-erythro-2-Amino-3methylpentanoic acid erythro-β-Hydroxyaspartic acid anti-Bicyclo[3.2.1]octan-8amine cis-1,2-Dichloroethene d-Camphor dl-2-Aminopropanoic Acid (E)-Diphenyldiazene endo-2-Chlorobicyclo[2.2.1]heptane (+)-erythro-2-Amino-3methylpentanoic Acid erythro-β-Hydroxyaspartic Acid exo-Bicyclo[2.2.2]oct-5-en-2-ol exo-Bicyclo[2.2.2]oct-5-en-2-ol exo-5,6-Dimethyl-endobicyclo[2.2.2]octan-2-ol L -threo-2,3-Dichlorobutyric acid meso-Tartaric acid (1R*,3S*)-1-Bromo-3chlorocyclohexane rel-(1R,3R)-1-Bromo-3chlorocyclohexane (S)-2,3-Dihydroxypropanoic acid sn-Glycerol 1-(dihydrogen phosphate) syn-7-Methylbicyclo[2.2.1]heptene trans-cisoid-transPerhydrophenanthrene (Z)-5-Chloro-4-pentenoic acid (1Z,4E)-1,2,4,5-Tetrachloro-1,4pentadiene exo-5,6-Dimethyl-endobicyclo[2.2.2]octan-2-ol L -threo-2,3-Dichlorobutyric Acid meso-Tartaric Acid (1R*,3S*)-1-Bromo-3chlorocyclohexane rel-(1R,3R)-1-Bromo-3chlorocyclohexane (S)-2,3-Dihydroxypropanoic Acid sn-Glycerol 1-(Dihydrogen phosphate) syn-7-Methylbicyclo[2.2.1]heptene trans-cisoid-transPerhydrophenanthrene (Z)-5-Chloro-4-pentenoic Acid (1Z,4E)-1,2,4,5-Tetrachloro-1,4pentadiene 240 ➤ The ACS Style Guide ➤ Use italic letters within square brackets in names of polycyclic aromatic compounds. dibenz[a,j]anthracene dibenzo[c,g]phenanthrene dicyclobuta[de,ij]naphthalene 1H-benzo[de]naphthacene indeno[1,2-a]indene Syllabic Portion of Chemical Names Multiplying afﬁxes are integral parts of the chemical name; they are set in roman type and are always closed up to the rest of the name (without hyphens). Use hyphens only to set off intervening locants or descriptors. Use enclosing marks (parentheses, brackets, or braces) to ensure clarity or to observe other recommended nomenclature conventions. Multiplying preﬁxes include the following: • hemi, mono, di, tri, tetra, penta, hexa, hepta, octa, ennea, nona, deca, deka, undeca, dodeca, etc. • semi, uni, sesqui, bi, ter, quadri, quater, quinque, sexi, septi, octi, novi, deci, etc. • bis, tris, tetrakis, pentakis, hexakis, heptakis, octakis, nonakis, decakis, etc. 3,4′-bi-2-naphthol 2,2′-bipyridine bis(benzene)chromium(0) 1,4-bis(3-bromo-1oxopropyl)piperazine 1,3-bis(diethylamino)propane di-tert-butyl malonate dichloride 1,2-ethanediol hemihydrate hexachlorobenzene 2,4,6,8-nonanetetrone pentachloroethane 3,4,5,6-tetrabromo-o-cresol tetrakis(hydroxymethyl)methane tri-sec-butylamine triamine triethyl phosphate tris(amine) 2,3,5-tris(aziridin-1-yl)-pbenzoquinone tris(ethylenediamine)cadmium dihydroxide Capitalization of Chemical Names Chemical names are not capitalized unless they are the ﬁrst word of a sentence or are part of a title or heading. Then, the ﬁrst letter of the syllabic portion is capitalized, not the locant, stereoisomer descriptor, or positional preﬁx. Table 12-1 presents examples of simple chemical names and their capitalization. Table 12-2 presents chemical names that include locants and descriptors. ➤ Some reaction names are preceded by element symbols; they may be used as nouns or adjectives. When they are the ﬁrst word of a sentence or appear in titles Chapter 12: Names and Numbers for Chemical Compounds ➤ 241 and headings, capitalize the ﬁrst letter of the word. Do not italicize the element symbol. N-Oxidation of the starting compounds yielded compounds 3–10. N-Benzoylated amines undergo hydroxylation when incubated with yeast. Preparation of S-Methylated Derivatives O-Substituted Structural and Functional Analogues Punctuation in Chemical Names ➤ Use commas between numeral locants, chemical element symbol locants, and Greek locants, with no space after the comma. When a single locant consists of a numeral and a Greek letter together with no space or punctuation, the numeral precedes the Greek letter. When the Greek letter precedes the numeral, they indicate two different locants and should be separated by a comma. For example, α,2 denotes two locants; 1α is viewed as one locant. (6α,11β,16α)-6-ﬂuoro-16-methylpregna-1,4-diene β,4-dichlorocyclohexanepropionic acid 1,2-dinitrobutane N,N-dimethylacetamide 2,3,3a,4-tetrahydro-1H-indole ➤ Use hyphens to separate locants and conﬁgurational descriptors from each other and from the syllabic portion of the name. α-ketoglutaric acid 2-benzoylbenzoic acid 1,4-bis(2-ethylhexyl) sulfosuccinate 3-chloro-4-methylbenzoic acid cis-dichloroethylene d-arabinose (1,4-dioxaspiro[4.5]dec-2-ylmethyl) guanidine (E)-2-(3,7-dimethyl-2,6-octadienyl)-1,4-benzenediol N-hydroxy-N-nitrosobenzeneamine N-methylmethanamine 4-O-β-d-galactopyranosyl-d-fructose tetrahydro-3,4-dipiperonyl-2-furanol trans-2-bromocyclopentanol ➤ Do not use hyphens to separate the syllables of a chemical name unless the name is too long to ﬁt on one line. Appendix 12-1 is a list of preﬁxes, sufﬁxes, roots, and some complete words hyphenated as they would be at the end of a line. 242 ➤ The ACS Style Guide Specialized Groups of Chemicals Polymers Polymer names are often one or two words in parentheses following the preﬁx “poly”. “Poly” is a syllabic preﬁx, not a descriptor, and thus is set in roman type. Here is a short list of correctly formatted names of frequently cited polymers. (These names are not necessarily IUPAC or CA index preferences.) nylon-6 nylon-6,6 polyacrylamide poly(acrylic acid) polyacrylonitrile polyamide poly(aryl sulfone) polybutadiene 1,2-polybutadiene 1,4-polybutadiene poly(butyl acrylate) poly(butyl methacrylate) poly(n-butyl methacrylate) poly(butylene terephthalate) polycarbonate polychloroprene poly(N,N-dimethylacrylamide) poly(dimethylsiloxane) polyester polyether poly(ether imide) poly(ether ketone) poly(ether sulfone) poly(ethyl acrylate) poly(ethyl methacrylate) polyethylene poly(ethylene adipate) poly(ethylene glycol) poly(ethylene oxide) poly(ethylene terephthalate) polyformaldehyde polyimidazole polyimide poly(isobutyl methacrylate) polyisobutylene polyisoprene poly(methacrylic acid) poly(methyl acrylate) poly(methyl methacrylate) poly(methylene) poly(N,N ′-hexamethyleneadipamide) poly(oxy-1,4-phenylene) poly(oxyethylene) poly(oxymethylene) poly(phenylene ether) poly(phenylene oxide) poly(phenylene sulﬁde) polypropylene poly(propylene glycol) polystyrene polysulﬁde polysulfone poly(tetraﬂuoroethylene) poly(tetramethylene oxide) polythiazole poly(thiocarbonate) polyurethane poly(vinyl acetate) poly(vinyl alcohol) poly(vinyl butyral) poly(vinyl chloride) poly(vinyl ether) poly(vinyl trichloroacetate) poly(vinylidene chloride) poly(vinylpyrrolidone) povidone ➤ In text, keep polymer names lowercase. As the ﬁrst word of a sentence and in titles or headings, capitalize only the ﬁrst letter of the polymer name. New Uses for Poly(ethylene terephthalate) Chapter 12: Names and Numbers for Chemical Compounds ➤ 243 Poly(vinyl chloride) is a less useful polymer than poly(ethylene glycol). Reactions of Poly(methyl methacrylate) ➤ In copolymer nomenclature, descriptive lowercase italic inﬁxes may be used. These include alt, blend, block (or b), co, cross, graft (or g), inter, per, stat, and ran. polybutadiene-graft-[polystyrene:poly(methyl methacrylate)] poly(cross-butadiene) poly[cross-(ethyl acrylate)]-inter-polybutadiene poly(ethylene-alt-carbon monoxide) polyisoprene-blend-polystyrene poly[(methyl methacrylate)-b-(styrene-co-butadiene)] poly[(methyl methacrylate)-co-styrene] polystyrene-block-polybutadiene poly(styrene-co-butadiene) poly(styrene-g-acrylonitrile) poly(vinyl trichloroacetate)-cross-polystyrene Saccharides Abbreviations for the major monosaccharides are presented in Table 12-3. ➤ Designation of the bond between two monosaccharides should specify the ﬁrst residue, its anomeric conﬁguration (α or β), the position of attachment on both sugar residues, and the second residue. Additional locants and conﬁgurational descriptors may be present but are not required. A number of variations may be used. Galβ1→4Glc Galβ1–4Glc Galβ1,4Glc Galβ(1→4)Glc Galβ(1–4)Glc Galβ(1,4)Glc Table 12-3. Abbreviations for Major Monosaccharides Saccharide arabinose fucose galactose N-acetylgalactosamine glucose N-acetylglucosamine glucuronic acid mannose N-acetylneuraminic acid N-glycoloylneuraminic acid rhamnose xylose Abbreviation Ara Fuc Gal GalNAc Glc GlcNAc GlcA Man Neu5Ac Neu5Gc Rha Xyl 244 ➤ The ACS Style Guide ➤ For larger oligosaccharides, use parentheses or brackets for branched residues: Manα1→6(Manα1→3)Manβ1→4GlcNAcβ1→4(±Fucα1→6)GlcNAc Manα(1–6)[Manα(1–3)]Manβ(1–4)GlcNAcβ(1–4)[±Fucα(1–6)]GlcNAc Nucleic Acids Table 12-4 presents the standard abbreviations for nucleic acids. ➤ By convention, numbering of the bases is unprimed and numbering of the sugars is primed. A nucleic acid polymer typically has the phosphate group attached to the 5′ position of the ﬁrst nucleotide (the 5′ end), and the other end terminates in a hydroxyl group at the 3′ position of the sugar of the last nucleotide (the 3′ end). By convention, nucleotide sequences are almost always read and presented in the 5′ to 3′ direction. The sequence may be presented in unbroken form or in evenly spaced blocks. 5′-TAGCTAACCCGTTTTAGCGTCGTC-3′ 5′-TAGCT AACCC GTTTT AGCGT CGTC-3′ ➤ Complementary base pairs are joined by hydrogen bonds and are best repre- sented by a centered dot: dA·dT and dG·dC are the canonical pairings in doublestranded DNA, although alternate pairings, DNA·RNA hybrids, triplexes, and other variations may occur. Table 12-4. Abbreviations for Nucleic Acids Abbreviation for Nucleosidea Nucleoside Monophosphateb Nucleoside Diphosphate Nucleoside Triphosphate Naturally occurring in RNA, ribonucleic acid adenine ribose adenosine, A cytosine ribose cytidine, C guanine ribose guanosine, G uracil ribose uridine, U AMP CMP GMP UMP ADP CDP GDP UDP ATP CTP GTP UTP Naturally occurring in DNA, deoxyribonucleic acid adenine deoxyribose deoxyadenosine, dA cytosine deoxyribose deoxycytidine, dC guanine deoxyribose deoxyguanosine, dG thymine deoxyribose thymidine, dTc dAMP dCMP dGMP dTMP dADP dCDP dGDP dTDP dATP dCTP dGTP dTTP Base Sugar (base + sugar) a Other nucleosides may occur (e.g., inosine, I, or xanthosine, X), but those listed are the canonical building blocks of nucleic acids and need never be defined. N may be used for an unspecified nucleoside or a mixture of all four (i.e., dNTPs were added to the reaction mixture). b c A nucleoside monophosphate is also known as a nucleotide. Thymidine consists of thymine + deoxyribose by definition and is abbreviated dT by definition; deoxythymidine would imply a different compound lacking another oxygen. Chapter 12: Names and Numbers for Chemical Compounds ➤ 245 Amino Acids ➤ The abbreviations of the essential 20 amino acids are listed in Table 12-5; these abbreviations do not need to be deﬁned. In analytical situations, undifferentiated mixtures of aspartic acid/asparagine (Asx, B) or glutamic acid/glutamine (Glx, Z) may occur. ➤ For amino acids other than the essential 20, three-letter abbreviations may be used and deﬁned at their ﬁrst appearance. homocysteine hydroxyproline norvaline ornithine Hcy Hyp Nva Orn Three-letter amino acid abbreviations may be preceded by a configurational designator, d or l, set in small capital letters. ➤ Always capitalize the three-letter and one-letter abbreviations for amino acids. ➤ In sequences of amino acids, separate the three-letter abbreviations with hyphens. Pro-Gln-Ile-Ala Table 12-5. Abbreviations for Amino Acids Amino Acid alanine arginine asparagine aspartic acid cysteine glutamic acid glutamine glycine histidine isoleucine leucine lysine methionine phenylalanine proline serine threonine tryptophan tyrosine valine Three-Letter Abbreviation Ala Arg Asn Asp Cys Glu Gln Gly His Ile Leu Lys Met Phe Pro Ser Thr Trp Tyr Val One-Letter Abbreviation A R N D C E Q G H I L K M F P S T W Y V 246 ➤ The ACS Style Guide ➤ Do not use abbreviations for individual amino acids in running text. Selective labeling of arginine and serine made it possible to monitor the kinetics of folding of the individual residues. ➤ Position numbers may follow one- or three-letter abbreviations or spelled- out names and may be closed up, hyphenated, spaced, or superscripted. Designation of a mutation includes the original amino acid, the position number, and the new amino acid: A134V Ala134Val alanine-134 → valine Combinatorial Compounds ➤ Combinatorial libraries are described by generic representations, which con- sist of a generic structure together with one or more lists of substituents. The position of substituents is indicated by superatoms in the generic structure. ➤ Superatoms are designated by roman letters: R for any set of substituents or residues, for example, or Ar for a list of aromatic substituents. Superatoms may be distinguished by the addition of designation digits, typically a subscript following the superatom: RA, RB, and RC could specify the residue of reagents A, B, and C. ➤ Subscript numbers are generally used to indicate the order in which residues were introduced to the reaction scheme: R1, R2, R3, and so on. ➤ The Journal of Combinatorial Chemistry recommends the use of ChemSet notation, in which a structure number is followed by the reagent sets associated with it. The structure number is typeset in bold, and the reagent sets are set in italics and enclosed in curly brackets. 1{1–5} + 2{1–6} + 4{1–4} → 5{1–5,1–4,1–6} 4{1–5,1–4,1–6} ➤ The composition of a ﬁnal library can be described in terms of mixtures or separate products. An uppercase X is used to indicate products mixed; an uppercase O is used to indicate products separate. 4{X,X,O} 4{X 1–5,X 1–4,O 1–6} 4{O,O,O} 4{O 1–5,O 1–4,O 1–6} Additional information on the representation of combinatorial chemistry is given in Appendix 12-2. ➤➤➤➤➤ APPENDIX 12-1 End-of-Line Hyphenation of Chemical Names This appendix contains a list of preﬁxes, sufﬁxes, roots, and some complete words hyphenated as they would be at the end of a line. To hyphenate a chemical name such as 5-(2-chloroethyl)-9-(diaminomethyl)-2-anthracenol look up each syllable that is to be hyphenated in the list. Also, chemical names can be broken after hyphens that are integral in their names. Follow other standard rules for hyphenation of regular words; for example, try to leave at least three characters on each line. Thus, the example given could be hyphenated as follows: 5-(2-chlo-ro-eth-yl)-9-(di-ami-no-meth-yl)-2-anth-ra-cenol Most desk dictionaries contain the names of common chemicals; they also give end-of-line hyphenation. ace-naph-tho ace-tal acet-al-de-hyde acet-amide acet-ami-do acet-amin-o-phen acet-an-i-lide ace-tate ac-et-azol-amide ace-tic ace-to ace-to-ace-tic ace-tone ace-to-ni-trile ace-tyl acet-y-late acet-y-lene acro-le-in ac-ryl-am-ide ac-ry-late acryl-ic ac-ry-lo ad-i-po-yl al-kyl al-lyl ami-di-no amide ami-do amine ami-no am-mine am-mo-nio am-mo-ni-um an-thra an-thra-cene an-thra-ce-no an-thryl ar-se-nate ar-si-no aryl az-i-do azi-no azo benz-ami-do ben-zene benz-hy-dryl ben-zo-yl ben-zyl ben-zyl-i-dene bi-cy-clo bo-ryl bro-mide bro-mo bu-tane bu-ten-yl bu-tyl bu-tyl-ene bu-tyl-i-dene car-ba-mate car-bam-ic car-ba-mide carb-an-ion car-ba-ryl 247 248 ➤ The ACS Style Guide car-ba-zole car-bi-nol car-bol-ic car-bon-ate car-bon-ic car-bo-ni-um car-bon-yl car-box-ami-do car-boxy car-box-yl car-byl-a-mi-no chlo-ride chlo-ro chlo-ro-syl chlo-ryl cu-mene cy-a-nate cy-a-nide cy-a-na-to cy-a-no cy-clo cy-clo-hex-ane cy-clo-hex-yl di-azo di-bo-ran-yl di-car-bon-yl di-im-ino di-oxy di-oyl diyl do-de-cyl ep-oxy eth-ane eth-a-no eth-a-nol eth-a-no-yl eth-en-yl eth-yl eth-yl-ene eth-yl-i-dene eth-yn-yl ﬂuo-res-cence ﬂuo-ride ﬂuo-ro form-al-de-hyde form-ami-do for-mic form-imi-do-yl for-myl fu-ran ger-myl gua-ni-di-no gua-nyl halo hep-tane hep-tyl hex-ane hex-yl hy-dra-zide hy-dra-zine hy-dra-zi-no hy-dra-zo hy-dra-zo-ic hy-dric hy-dride hy-dri-od-ic hy-dro hy-dro-chlo-ric hy-dro-chlo-ride hy-dro-chlo-ro hy-drox-ide hy-droxy hy-drox-yl imi-da-zole imide imi-do imi-do-yl imi-no in-da-mine in-da-zole in-dene in-de-no in-dole io-date io-dide iodo io-do-syl io-dyl iso-cy-a-na-to iso-cy-a-nate iso-cy-a-nide iso-pro-pen-yl iso-pro-pyl mer-cap-to mer-cu-ric meth-an-ami-do meth-ane meth-ano meth-yl meth-yl-ate meth-yl-ene meth-yl-i-dene mono mono-ac-id mono-amine naph-tha-lene naph-tho naph-thyl neo-pen-tyl ni-trate ni-tric ni-trile ni-trilo ni-trite ni-tro ni-troso oc-tane oc-tyl ox-idase ox-ide ox-ido ox-ime oxo ox-o-nio oxy palm-i-toyl pen-tane pen-tyl pen-tyl-i-dene per-chlo-rate per-chlo-ride per-chlo-ryl per-man-ga-nate per-ox-idase per-ox-ide per-oxy phen-ac-e-tin phen-an-threne Chapter 12: Names and Numbers for Chemical Compounds phen-an-thro phen-an-thryl phen-a-zine phe-no phe-nol phe-none phen-ox-ide phen-oxy phen-yl phen-yl-ene phos-phate phos-phide phos-phine phos-phi-no phos-phin-yl phos-phite phos-pho phos-pho-nio phos-pho-no phos-phor-anyl phos-pho-li-pase phos-pho-lip-id phos-pho-ni-um phos-pho-ric phos-pho-rus phos-pho-ryl plum-byl pro-pane pro-pen-yl pro-pen-yl-ene pro-pyl pro-pyl-ene pro-pyl-i-dene pu-rine py-ran pyr-a-zine pyr-a-zole pyr-i-dine pyr-id-a-zine pyr-role quin-o-line qui-none sel-e-nate se-le-nic sel-e-nide sel-e-nite se-le-no si-lane sil-anyl sil-ox-anyl sil-ox-yl si-lyl spi-ro stan-nic stan-nite stan-nous stan-nyl stib-ino sty-rene sty-ryl sul-fa-mo-yl sul-fate sul-fe-no sul-fe-nyl sul-ﬁde sul-ﬁ-do sul-ﬁ-no sul-ﬁ-nyl sul-ﬁte sul-fo sul-fon-ami-do sul-fo-nate sul-fone sul-fon-ic sul-fo-nio sul-fo-nyl sulf-ox-ide sul-fu-ric sul-fu-rous sul-fu-ryl tet-ra thio thio-nyl thio-phene thi-oxo thi-oyl tol-u-ene tol-u-ide tol-yl tri-a-zine tri-a-zole tri-yl urea ure-ide ure-ido uric vi-nyl vi-nyl-i-dene xan-thene xan-tho xy-lene xy-li-dine xy-lyl xy-li-din-yl yl-i-dene ➤ 249 ➤➤➤➤➤ APPENDIX 12-2 Representation of Combinatorial Chemistry Derek Maclean Combinatorial chemistry entails the reaction of sets of reagents to produce sets or libraries of products in numbers up to the size of each reagent set multiplied together. Thus 5 reagents A, plus 4 reagents B, plus 6 reagents C could prepare 5 × 4 × 6, or 120 products ABC. The unique feature of this strategy is the ability to efﬁciently prepare very large numbers of compounds—a so-called combinatorial library. The challenges in describing combinatorial chemistry consist of concisely but accurately reporting the constituents and form of such a compound collection. The individual products of combinatorial chemistry are called members. The distinction between a member and a compound is important and is based on the respective level of characterization. A compound will meet the typical standards for reporting new chemical structures; a member will fall short of that standard. In fact, a member may, in principle, simply be expected to be present in a library, especially for large libraries, and those that consist of mixtures rather than discrete samples of members. The structural representation of combinatorial chemistry consists of a generic structure plus a list of substituents that may be present in that structure. The generic structure is very similar to a typical structural formula with the addition of special notation to indicate the potential for variable substitution at certain parts of the molecule. The position of variable substituents on a generic structure is indicated by superatoms, such as the R designation. In a combinatorial library, R need not simply designate an alkyl radical but is conventionally used to represent any set of substituents or residues. The residues R typically deﬁne those portions of reagents or building blocks that are found in the ﬁnal product of the synthesis and that vary among library members. Particular superatoms may more precisely deﬁne the composition of a library, such as Ar for a list of aromatic substituents. To distinguish superatoms within a generic structure, it is typical to use additional designation digits. Thus RA, RB , and RC could specify the residue of reagents A, B, and C in our example. The position of the additional digit has 250 Chapter 12: Names and Numbers for Chemical Compounds ➤ 251 not been standardized but may be typically added as a subscript following the superatom. The designation digit may usefully convey additional information beyond the simple differentiation of superatoms. For instance, R1, R2, R3, and so on may indicate the order in which these residues were introduced to the reaction scheme. Alternatively, RX or RO make use of the pool designations X and O (see the section “ChemSet Notation”) to concisely describe library composition in a generic structure. It is often possible to draw multiple generic structures for a combinatorial library. Care should be taken in the choice of the appropriate structure, taking into account the purpose for the structure. Often the maximum common substructure is a good choice, but other structures may better illustrate structure–activity relationships or the synthetic potential of a combinatorial reaction strategy. The relationship between residue and reagent or product should be deﬁned. This may be conveniently shown in the generic reaction scheme; see Figure 12A-1. A typical feature of combinatorial synthesis is the use of techniques that facilitate the isolation of products and intermediates. The most common example is the attachment to a solid support, such as a polymer bead, to allow isolation by simple ﬁltration (solid-phase chemistry). A variety of solid and soluble supports have been developed. These may be attached to either the products or the reagents of a library. Such supports can be dealt with in generic reaction schemes as a special type of superatom. Often, a pictorial representation is used. A polymer bead may be conveniently represented by an s orbital in common chemistry software packages. Few standards have been developed for the representation of other supports, but a ﬁlled structure designates a solid support and an open structure may be used for a soluble support. ChemSet Notation A convenient descriptive notation for combinatorial libraries (recommended by the Journal of Combinatorial Chemistry) is the ChemSet terminology. A ChemSet is denoted by a structure number followed by the reagent sets associated with that structure. Thus the combinatorial library with 120 products could be described as follows, where the numbers in curly brackets deﬁne the reagents which were used to prepare that library; see Figure 12A-1. 5{1–5,1–6,1–4} The synthetic scheme to prepare such a library may also be described in terms of ChemSets: 1{1–5} + 2{1–6} + 4{1–4} → 5{1–5,1–6,1–4} The composition of the final library may consist of a mixture of all members, or as a collection of discrete product samples, or as a set of smaller pools. An exten- 252 ➤ The ACS Style Guide R2-CHO 2{1–6} R1 O NH2 R3-COCl 4{1–4 } R1 O N O O 1{1–5 } 3{1–5,1–6 } R2 R1 O N O O R2 R3 5{1–5,1–6,1–4 } Figure 12A-1. Combinatorial reaction scheme and ChemSet notation. Source: Reprinted from J. Am. Chem. Soc. 1996, 118, 253–254. Copyright 1996 American Chemical Society. sion to the ChemSet notation allows these situations to be precisely defined. The useful designations X and O indicate respectively, “products mixed” and “products separate”. Thus, the library 5{X 1–5,X 1–6,O 1–4} is a set of 6 pools, each with 20 members deriving from a single reagent from set 4, since the O indicates that the six individual product mixtures were kept separate from one another after adding reagents 4. In contrast, 5{O 1–5,O 1–4,O 1–6} represents 120 discrete product samples, also called parallel synthesis, since the O for each set indicates that all products were kept separate at each stage. If all of a given set of reagents have been used in a given pool, then the number for that set may be omitted. Thus, 5{X,X,O} and 5{O,O,O} accurately describe the composition of the above libraries. However, if a subset of possible reagents have been used, this must be indicated using the numerical list format, e.g., 5{X 1–6,O 1–2,3}. ➤➤➤➤➤ APPENDIX 12-3 CAS Registry Numbers Chemical substances, their syntheses, the determination of their properties, and their applications are the core of chemistry and the main occupation of chemists. In their communications, chemists represent chemical substances by structural diagrams, names, molecular formulas, codes, and identiﬁcation numbers. One of the most frequently used identiﬁcation numbers is the CAS Registry Number. Today, CAS Registry Numbers are often used to identify chemical substances in handbooks, indexes, databases, and inventories, and even on many commercial product labels. The CAS Chemical Registry System is a computer-based system that uniquely identiﬁes chemical substances on the basis of their molecular structures. Begun originally in 1965 to support indexing for Chemical Abstracts (CA), the CAS Chemical Registry System now serves not only as a support system for identifying substances within Chemical Abstracts Service operations but also as an international resource for chemical substance identiﬁcation by scientists, industry, and regulatory bodies. The CAS Registry provides a means of bridging the many differences in systematic, generic, proprietary, and trivial substance names that may be used to identify a single substance. The CAS Chemical Registry System database is the largest collection of information on naturally occurring and synthetic chemical substances in the world, including organic compounds, inorganic compounds, organometallics, metals, polymers, coordination compounds, alloys, elements, isotopes, nuclear particles, proteins, nucleic acids, and minerals. By the end of 2005, the CAS Chemical Registry System contained records for more than 27 million organic and inorganic substances, with new records added at the rate of some 5000 per day. A running total of registered substances can be found on the CAS Web site at http://www. cas.org/cgi-bin/regreport.pl. The database contains CAS Registry Numbers, structures, and names for substances reported in the chemical literature covered in CA, in addition to substances registered from special collections, for governmental and industrial organizations, and for individual requesters. CAS Registry Numbers are also assigned to sequences such as DNA and proteins. CAS Registry Numbers are assigned in sequential order as substances are entered into the CAS Chemical Registry System database for the ﬁrst time; the numbers have no chemical signiﬁcance. CAS Registry Numbers link the molecular structure diagram, systematic CA index name, synonyms, molecular formula, 253 254 ➤ The ACS Style Guide and other identifying information for each substance. Because CAS Registry Numbers are independent of the many different systems of chemical nomenclature, they can bridge these systems and link often unrecognized synonymous names. A format was developed using hyphens to make the numbers easier to read and to recognize. A CAS Registry Number includes up to nine digits that are separated into three parts by hyphens. The ﬁrst part, starting from the left, has up to six digits, the second part has two digits, and the ﬁnal part is a single check digit to verify the validity of the total number (e.g., 7732-18-5 for water). Within the registry system, each substance is assigned a separate CAS Registry Number. For example, each salt of an acid receives a distinct number, and an ion receives a number different from that of the neutral compound. CAS Registry Numbers are included in the printed Chemical Abstracts chemical substance and formula indexes and in the CAS databases. The full set of CAS Chemical Registry System database information—structures, names, formulas, and ring data—is available for search and display through STN International, SciFinder, and other CAS search services. CAS Registry information is also available in CAS databases offered by other online system vendors. In addition to their inclusion in the CAS databases, CAS Registry Numbers are used in many public and private databases. Many handbooks, guides, and other reference works include CAS Registry Numbers and provide special indexes that allow the reader to ﬁnd the proper place in the text without ﬁrst having to identify the full name of the substance. The reader beneﬁts because the full name may differ from handbook to handbook. CAS Registry Numbers are also widely used as standard identiﬁers for chemical substances in many of the commercial chemical inventories of governmental regulatory agencies, such as the Toxic Substances Control Act (TSCA) Inventory in the United States, the European Inventory of Existing Commercial Chemical Substances (EINECS), and the Canadian Domestic and Non-Domestic Substance Lists (DSL/NDSL). Whenever a chemical substance is sold, transported, imported, exported, reported to a regulatory agency, or disposed of, a CAS Registry Number is probably involved. ➤➤➤➤➤ CHAPTER 13 Conventions in Chemistry T his chapter presents a quick reference guide for the use of typefaces (roman, italic, and bold), Greek letters, superscripts and subscripts, and special symbols that are commonly used in chemistry. Appendix 13-1 presents the symbols for commonly used physical quantities. Detailed recommendations from the International Union of Pure and Applied Chemistry (IUPAC, http://www.iupac.org) are given in the book titled Quantities, Units and Symbols in Physical Chemistry, 2nd edition, nicknamed the “green book”, published by Blackwell Science, Oxford, U.K., 1993. Updates are published as articles in the journal Pure and Applied Chemistry. Detailed recommendations from the International Organization for Standardization (ISO, http://www.iso.org) are given in the ISO Standards Handbook 2, Quantities and Units, published by ISO, Geneva, Switzerland, 1993. Some individual standards have been amended, and their updates are available at http:// www.iso.org/iso/en/prods-service/ISOstore/store.html. The National Institute of Standards (NIST) Special Publication 330, 2001 Edition, available at http:// physics.nist.gov/Pubs/SP330/sp330.pdf, is the U.S. updated edition of the English version of the Bureau International des Poids et Mesures. The booklet The International System of Units (SI), 7th ed., published by the International Bureau of Weights and Measures (BIPM), Sèvres, France, 1998, is the deﬁnitive reference on SI units. Some books and journals follow IUPAC recommendations for representations of various chemical conventions. Some specify the use of ISO standards. Others are less stringent as long as the manuscript is consistent in usage within itself. Always consult the author guidelines. Copyright 2006 American Chemical Society 255 256 ➤ The ACS Style Guide Subatomic Particles and Quanta ➤ Use lowercase Latin or Greek letters for abbreviations for subatomic particles. alpha particle beta particle deuteron electron helion muon α β d e h µ± neutrino neutron photon pion proton triton νe n γ π p t ➤ Indicate electric charges with the appropriate superscript (+, –, or 0). n0 e+ e– π± If the symbols p and e are used without indication of charge, they refer to positive proton and negative electron, respectively. Electronic Conﬁguration ➤ Denote electron shells with the uppercase roman letters K, L, M, and N. ➤ Name electron subshells and atomic orbitals with the lowercase roman letters s, p, d, and f. Write principal energy levels 1–7 on the line and to the left of the letter; give the number of electrons in the orbital as a superscript to the right of the letter. Specify orbital axes with italic subscripts. 7s electron 3d44s4p2 conﬁguration 2 5f ions pxpypz 5f orbital dxzdyzdxy 6d orbital dz2 sp3 hybrid orbital dx2–y2 fn–3ds2 conﬁguration The ground state of boron is 1s22s22px12py02pz0. The valence-shell conﬁguration of nitrogen is 2s22px12py12pz1. The electronic conﬁguration of potassium is 1s22s22p63s23p64s1. The valence-electron conﬁguration is described by 5d106s1. ➤ Use Greek letters for some bonding orbitals and the bonds they generate. π bond σ orbital σ∗ orbital Chapter 13: Conventions in Chemistry ➤ 257 ➤ Name the electronic states of atoms with the uppercase roman letters S, P, D, F, G, H, I, and K, corresponding to quantum numbers l = 0–7. Use the corresponding lowercase letters to indicate the orbital angular momentum of a single electron. The left superscript is the spin multiplicity; the right subscript is the total angular momentum quantum number J. 2S 0 2s 0 8F 1/2 8f 1/2 4P 1/2 4p 1/2 8G 1/2 8g 1/2 7F 0 7f 0 2P 3/2 2p 3/2 7D 1 7d 1 ➤ Name the electronic states of molecules with the uppercase roman letters A, B, E, and T; the ground state is X. Use the corresponding lowercase letters for oneelectron orbitals. A tilde (~) is added for polyatomic molecules. The subscripts describe the symmetry of the orbital. Ã 2 A1g A2g ã 2 a1g a2g 3 B1 3 b1 Eg E2g eg e2g T2g t2g Chemical Elements and Formulas ➤ Write the names of the chemical elements in roman type and treat them as common nouns. oxygen seaborgium uranium francium helium hydrogen calcium californium carbon einsteinium ➤ Write the symbols for the chemical elements in roman type with an initial capital letter. Ca Cf C Es Fr He H O Sg U The complete list of chemical elements and symbols is given in Table 13-1. ➤ Even when symbols are used, the element’s name is pronounced. Therefore, choose the article (a or an) preceding the element symbol to accommodate the pronunciation of the element name. (This usage does not apply to isotopes, as described in the section on isotopes.) a Au electrode (pronounced “a gold electrode”) a N-containing compound (pronounced “a nitrogen-containing compound”) a He–Ne laser (pronounced “a helium–neon laser”) 258 ➤ The ACS Style Guide Table 13-1. Atomic Weights of the Elements 2001 Name Actinium Aluminum Americium Antimony Argon Arsenic Astatine Barium Berkelium Beryllium Bismuth Bohrium Boron Bromine Cadmium Calcium Californium Carbon Cerium Cesium Chlorine Chromium Cobalt Copper Curium Dubnium Dysprosium Einsteinium Erbium Europium Fermium Fluorine Francium Gadolinium Gallium Germanium Gold Hafnium Hassium Helium Holmium Hydrogen Indium Iodine Iridium Iron Krypton Lanthanum Sym. Ac Al Am Sb Ar As At Ba Bk Be Bi Bh B Br Cd Ca Cf C Ce Cs Cl Cr Co Cu Cm Db Dy Es Er Eu Fm F Fr Gd Ga Ge Au Hf Hs He Ho H In I Ir Fe Kr La No. 89 13 95 51 18 33 85 56 97 4 83 107 5 35 48 20 98 6 58 55 17 24 27 29 96 105 66 99 68 63 100 9 87 64 31 32 79 72 108 2 67 1 49 53 77 26 36 57 Atomic Wt. Notes * 26.981538(2) * g 121.760(1) g, r 39.948(1) 74.92160(2) * 137.327(7) * 9.012182(3) 208.98038(2) * g, m, r 10.811(7) 79.904(1) g 112.411(8) g 40.078(4) * g, r 12.0107(8) g 140.116(1) 132.90545(2) g, m, r 35.453(2) 51.9961(6) 58.933200(9) r 63.546(3) * * g 162.500(1) * g 167.259(3) g 151.964(1) * 18.9984032(5) * g 157.25(3) 69.723(1) 72.64(1) 196.96655(2) 178.49(2) * 4.002602(2) g, m 164.93032(2) g, m, r 1.00794(7) 114.818(3) 126.90447(3) 192.217(3) 55.845(2) g, m 83.798(2) 138.9055(2) g Name Lawrencium Lead Lithium Lutetium Magnesium Manganese Meitnerium Mendelevium Mercury Molybdenum Neodymium Neon Neptunium Nickel Niobium Nitrogen Nobelium Osmium Oxygen Palladium Phosphorus Platinum Plutonium Polonium Potassium Praseodymium Promethium Protactinium Radium Radon Rhenium Rhodium Rubidium Ruthenium Rutherfordium Samarium Scandium Seaborgium Selenium Silicon Silver Sodium Strontium Sulfur Tantalum Technetium Tellurium Sym. Lr Pb Li Lu Mg Mn Mt Md Hg Mo Nd Ne Np Ni Nb N No Os O Pd P Pt Pu Po K Pr Pm Pa Ra Rn Re Rh Rb Ru Rf Sm Sc Sg Se Si Ag Na Sr S Ta Tc Te No. Atomic Wt. Notes 103 * g, r 82 207.2(1) g, m, r 3 6.941(2)† g 71 174.967(1) 12 24.3050(6) 25 54.938049(9) 109 * 101 * 80 200.59(2) g 42 95.94(2) g 60 144.24(3) g, m 10 20.1797(6) 93 * 28 58.6934(2) 41 92.90638(2) g, r 7 14.0067(2) 102 * g 76 190.23(3) g, r 8 15.9994(3) g 46 106.42(1) 15 30.973761(2) 78 195.078(2) 94 * 84 * 19 39.0983(1) 59 140.90765(2) 61 * 91 231.03588(2)* 88 * 86 * 75 186.207(1) 45 102.90550(2) g 37 85.4678(3) g 44 101.07(2) 104 * g 62 150.36(3) 21 44.955910(8) 106 * r 34 78.96(3) r 14 28.0855(3) 47 107.8682(2) g 11 22.989770(2) g, r 38 87.62(1) g, r 16 32.065(5) 73 180.9479(1) 43 * g 52 127.60(3) Continued on next page Chapter 13: Conventions in Chemistry ➤ 259 Table 13-1. Atomic Weights of the Elements 2001—Continued Name Terbium Thallium Thorium Thulium Tin Titanium Tungsten Ununbium Ununhexium Ununnilium Sym. Tb Tl Th Tm Sn Ti W Uub Uuh Uun No. 65 81 90 69 50 22 74 112 116 110 Atomic Wt. Notes 158.92534(2) 204.3833(2) 232.0381(1)* g 168.93421(2) g 118.710(7) 47.867(1) 183.84(1) * * * Name Ununquadium Unununium Uranium Vanadium Xenon Ytterbium Yttrium Zinc Zirconium Sym. No. Atomic Wt. Notes Uuq 114 * Uuu 111 * U 92 238.02891(3)* g, m V 23 50.9415(1) g, m Xe 54 131.293(6) g Yb 70 173.04(3) Y 39 88.90585(2) Zn 30 65.409(4) g Zr 40 91.224(2) Notes: Scaled to the relative atomic mass, Ar(12C) = 12, where 12C is a neutral atom in its nuclear and electronic ground state. The atomic weights of many elements are not invariant but depend on the origin and treatment of the material. The standard values of Ar(E) and the uncertainties (in parentheses following the last significant figure to which they are attributed) apply to elements of natural terrestrial origin. The footnotes to this table elaborate the types of variation that may occur for individual elements and that may be larger than the listed uncertainties of values of Ar(E). Names of elements with atomic numbers 110 to 116 are provisional. *Element has no stable nuclides. However, three such elements (Pa, Th, and U) do have a characteristic terrestrial isotopic composition, and for these an atomic weight is tabulated. †Commercially available Li materials have atomic weights that range between 6.939 and 6.996; if a more accurate value is required, it must be determined for the specific material. g Geological specimens are known in which the element has an isotopic composition outside the limits for normal material. The difference between the atomic weight of the element in such specimens and that given in the table may exceed the stated uncertainty. m Modified isotopic compositions may be found in commercially available material because it has been subjected to an undisclosed or inadvertent isotopic fractionation. Substantial deviations in atomic weight of the element from that given in the table can occur. r Range in isotopic composition of normal terrestrial material prevents a more precise Ar(E) being given; the tabulated Ar(E) value should be applicable to any normal material. Source: Reprinted with permission from IUPAC, 2003. Copyright 2003 IUPAC. ➤ Write the names of chemical compounds in roman type and treat them as common nouns. (Names for chemical compounds are discussed further in Chapter 12.) isopropyl iodide magnesium sulfate mercuric sulfate methyl salicylate phenol sodium hydroxide benzaldehyde calcium carbonate chlorobenzene ethanol hydrochloric acid iron(III) nitrate ➤ Use roman type for the symbols for chemical compounds. BaSO4 C2H5OH C6H5Cl C6H5OH CaCO3 CH3COOH Fe(NO3)3 H3PO4 HCl HgSO4 NaOH Ni3P2O8 P2S5 VF5 Zn(C2H3O2)2 260 ➤ The ACS Style Guide ➤ You may use both chemical symbols and element names in text, but it is best to use one or the other consistently. Do not mix symbols and words within a name. NaCl or sodium chloride, not Na chloride ➤ Unnamed elements may be designated by using the atomic number (for example, element 125). They may also be designated by using the systematic name or symbol devised by IUPAC for elements of atomic number greater than 100 that have not yet received trivial names. In this system, an element name consists of a series of numerical roots corresponding to the numerals in the atomic number of the element, followed by “ium”. The roots are as follows: 0 1 2 3 4 5 6 nil un bi tri 7 8 9 quad pent hex sept oct enn The symbols consist of the first letters of the numerical roots. examples element 146 element 187 element 209 element 290 element 501 element 502 element 503 element 900 unquadhexium unoctseptium binilennium biennilium pentnilunium pentnilbium pentniltrium ennilnilium Uqh Uos Bne Ben Pnu Pnb Pnt Enn Drop the final “n” in “enn” when it is followed by “nil” (see elements 290 and 900) and the final “i” in “bi” and “tri” when they are followed by “ium” (see elements 502 and 503). ➤ You may use common abbreviations for organic groups in formulas and structures, but not in text. These (and only these) abbreviations need not be deﬁned. Ac Ar Bu i-Bu sec-Bu t-Bu Bz acetyl aryl butyl isobutyl sec-butyl tert-butyl benzoyl Bn, Bzl Et Me Ph Pr i-Pr R, R′ benzyl ethyl methyl phenyl propyl isopropyl alkyl ➤ Use square brackets in formulas for coordination entities. [Cr(C6H6)2] K[PtCl3(C2H4)] Chapter 13: Conventions in Chemistry ➤ 261 ➤ In the formula for an addition compound, use a centered dot, closed up on each side. (Although the IUPAC books show a space on each side, this spacing would wreak havoc with many typesetting systems.) BH3·NH3 Ni(NO3)2·2Ni(OH)2 Water of hydration follows a centered dot, closed up on each side. Na2SO4·10H2O Zn(NO3)2·H2O ➤ Use either a slash or an en dash between components of a mixture, but not a colon. dissolved in 5:1 glycerin/water dissolved in 5:1 glycerin–water the metal/ligand (1:1) reaction mixture the metal–ligand (1:1) reaction mixture the metal–ligand (1/1) reaction mixture the methane/oxygen/argon (1/50/450) matrix the methane/oxygen/argon (1:50:450) matrix Reference to the Periodic Table ➤ Always use lowercase for the word “group”, even with a speciﬁc number. group 15 elements group IVB elements ➤ Always use lowercase for the words “periodic table”. The elements in group 8 of the periodic table include Fe, Ru, and Os. Atoms and Molecules Nuclide descriptors are speciﬁed with superscripts and subscripts to the element symbol, as follows. Use the Left Superscript for Mass Number ➤ The mass number of an atom is usually shown only for isotopes or in dis- cussions of isotopes. 12C 35Cl 32S 262 ➤ The ACS Style Guide Use the Left Subscript for Atomic Number ➤ The atomic number of an atom is usually used only in discussions of nuclear chemistry. 6C 16S Use the Right Superscript for Ionic Charge ➤ The charge number is followed by the sign of the ionic charge. When the charge number is 1, only the sign is used. Ca2+ Na+ NO3– ➤ Stagger the subscript and superscript; do not align them. The subscript comes ﬁrst with ionic charge. PO43– ➤ Do not use multiple plus or minus signs, and do not circle the charge. Hg2+ (not Hg++) Use the Right Asterisk for Excited Electronic State He∗ NO∗ Use the Right Superscript for Oxidation Number ➤ You may use superscript roman numerals for oxidation numbers. In for- mulas, do not use numbers on the line to avoid confusion with the symbols for iodine or vanadium. CoIII FeIICl2 MnIII/IV MnIII–MnIV MnIII/MnIV MnIVO2 (NH3)2PtII Ni0 O–II PbIVO2 RuII–RuIII RuII/RuIII ➤ Stagger the subscript and superscript; do not align them. The subscript follows the superscript with oxidation number. PbII2 ➤ You may also write oxidation numbers on the line in parentheses closed up to the element name or symbol. Chapter 13: Conventions in Chemistry ➤ 263 cobalt(III) or Co(III) copper(II) or Cu(II) diammineplatinum(II) ferrate(VI) ion iron(II) or Fe(II) iron(II) chloride manganese(IV) oxide Mn(III)–Mn(IV) complex Mn(III)/Mn(IV) complex potassium tetracyanonickelate(0) Use the Right Subscript for Number of Atoms ➤ With an element symbol, use a subscript to indicate the number of atoms, whether in formulas or in narrative text. Al2O3 (CH3)4C H2S Fe3 C6 NH4 C6H5CH3 FeSi2 The C60 fullerene molecule is shaped like a soccer ball. ➤ With an element name, follow the usual conventions for numbers in text. Molecules composed of 60 carbon atoms are shaped like soccer balls. In this reaction, three hydrogen atoms are lost. Atom in a Speciﬁc Position ➤ Use either words or symbols and numbers on the line to refer to an atom in a speciﬁc position. at the carbon in the 6-position or at C6 or at C-6 the atom in the β-position or the β atom Isotopes ➤ Specify the isotope of an element by a mass number written as a left superscript to the element symbol. 13 C N 32 S 29 Si 235 U 15 264 ➤ The ACS Style Guide ➤ Alternatively, indicate an isotope by using the spelled-out element name hyphenated to its mass number. carbon-14 uranium-235 ➤ In either case, the isotope name or symbol is pronounced ﬁrst, then the num- ber. Thus, 14C is pronounced “c fourteen”. Consequently, choose the article (a or an) preceding the isotope to accommodate the pronunciation of the element name or symbol, not the number. a 14C isotope (pronounced “c fourteen”) an 3H isotope (pronounced “aitch three”) an 15N isotope (pronounced “en ﬁfteen”) a carbon-14 isotope a hydrogen-3 isotope a nitrogen-15 isotope ➤ Use the symbols 2H or D for deuterium and 3H or T for tritium when no other nuclides are present. D2O CD2H2 3H 2 CH3O3H (T2N)2CO HDSO4 2H S 2 CH2TOH 3H 2 An isotopically unmodiﬁed compound is one whose isotopic nuclides are present in the proportions that occur in nature. An isotopically modiﬁed compound has a nuclide composition that deviates measurably from that occurring in nature. An isotopically substituted compound has a composition such that all of the molecules of the compound have only the indicated nuclides at the designated positions. To indicate isotopic substitution in formulas, the nuclide symbols are incorporated into the formulas. To indicate isotopic substitution in spelled-out compound names, the number and symbol (and locants if needed) are placed in parentheses closed up to the name. N15NF2 24 NaCl H2N14CONH2 14 CH4 238 UCl3 PO43– Mo(12CO)6 Na235S 32 (15N)ammonia (14C6)glucose (1,3-3H2)benzene 1-chloro(2-3H)benzene An isotopically labeled compound is a mixture of an isotopically unmodiﬁed compound with an analogous isotopically substituted compound or compounds. Isotopically labeled compounds may be speciﬁcally labeled or selectively labeled. To indicate isotopic labeling, the number and symbol (and locants if needed) are enclosed in square brackets closed up to the compound name or formula. specifically labeled: [14C]H4 CH2[2H2] CH3CH2[18O]H Chapter 13: Conventions in Chemistry ➤ 265 selectively labeled: [2H]CH4 [2H]PH3 [36Cl]SOCl2 [6,7-15N]adenosine [15N]alanine [15N]ammonium chloride [1,3-3H2]benzene [57Co]cyanocobalamin 2,4-diamino[18O]phenol [2,8-3H]inosine [2-14C]leucine ➤ When the isotope position is speciﬁed by a group name that is part of the parent compound, italicize the group name. [methyl-14C]toluene ➤ Isotopically labeled compounds may also be described by inserting the symbol in brackets into the name of the compound. hydrogen [36Cl]chloride [35S]sulfuric [2H]acid ➤ Do not use the left superscript within an abbreviation. [32P]CMP (not CM32P) ➤ To indicate general labeling, use the symbol G in the names of selectively labeled compounds in which all positions of the designated element are labeled, but not necessarily in the same isotopic ratio. d-[G-14C]glucose ➤ To indicate uniform labeling, use the symbol U in the names of selectively labeled compounds in which all positions of the designated element are labeled in the same isotopic ratio. d-[U-14C]glucose ➤ When it is unknown or irrelevant whether the compound is isotopically labeled or isotopically substituted, simply hyphenate the isotope symbol to the compound name and do not use square brackets or parentheses. 14 C-glucose H-benzene 15 N-adenosine 3 The Boughton system, used in Chemical Abstracts, does not distinguish between labeling and substitution. The isotopic variation is shown by the symbol for the isotope (with a subscript numeral to indicate the number of isotopic atoms) placed after the name or relevant portion of the name; locants are cited 266 ➤ The ACS Style Guide if necessary. The locants and symbols are in italics, except subscripts and Greek letters, and hyphens are used to separate them. acetamide-1-13C-15N acetic-17O2 acid benzeneacetic-carboxy,α-14C2 acid benzoic-18O acid 4-(2-propenyl-3-13C-oxy)benzoic acid toluene-methyl-14C ➤ In this system, deuterium and tritium are represented by italic lowercase let- ters d and t, respectively. acetic-t3 acid-t alanine-N,N,1-d3 ammonia-d-t ethane-1-d-2-t 1-(ethyl-2,2,2-d3)-4-(methyl-d3)benzene methan-t-ol methane-d4 tri(silyl-d3)phosphine urea-t4 Radicals ➤ In the formula of a free radical, indicate the unshared electron by a superscript or centered dot closed up to the element symbol or formula. The superscript dot comes after the symbol or formula; centered dots come before or after the symbol or formula. Br• Br• •CH3 C6H5• H• HO• •NH2 •SH (SiH3)• •SnH3 ➤ Charged radical cations and anions are often indicated by the symbol, formula, or structure with a superscript dot followed by a plus or minus sign. However, in mass spectrometry, the reverse is used. Therefore, use the order of dots and signs for charges that is appropriate for the context. (Ag2)•+ C6H5NO•3– HCO•+ mass spectrometry C3H6+• R+• R•– R2•+ R(•)(2–) (SO2) • – Chapter 13: Conventions in Chemistry ➤ 267 Bonds ➤ For linear formulas in text, do not show single bonds unless the bonds are the subject of the discussion. C6H5CH3 C6H5COOCOCH3 CH3CHOHCH3 CH3COOH H2SO4 ➤ When necessary for the discussion, indicate bonds by en dashes. the –CH2– segment the C–H distances the C–C–C angle (–CH2–CH(CH3)–O–)n ➤ When necessary, show double and triple bonds in linear formulas. CH3C≡CH CH2=CH2 R–C–OH is better as RCOOH or RCO2H or RC(=O)OH || O ➤ Use three centered dots to indicate association of an unspeciﬁed type (e.g., hydrogen bonding, bond formation, or bond breaking). CPt FH–NH3 H2Oπ aromatic hydrogen bonding Mg2+O– NiAl Crystallography Planes and Directions in Crystals ➤ Miller indices of a crystal face or a single net plane are enclosed in parentheses. (123) or (hkl) is a plane or set of planes that describe crystal faces; (h1h2h3) is a single net plane. ➤ Laue indices are not enclosed. 123 or hkl is the Bragg reﬂection from the set of net planes (123) or (hkl), respectively. 268 ➤ The ACS Style Guide ➤ Indices of a set of all symmetrically equivalent crystal faces or net planes are enclosed in braces. {hkl} is a form. ➤ Indices of a zone axis or lattice direction are enclosed in square brackets. [123] or [uvw] is a direction. ➤ Indices of a set of symmetrically equivalent lattice directions are enclosed in angle brackets. represents all crystallographically equivalent directions of the type [uvw]. 120 1,10,1 11,0,1 1,–2,0 reﬂections the (111) face the (120) face the [001] axis the [010] direction the [101] direction h00 diffraction lines the hk0 zone the 002 reﬂection the 00l class of reﬂections ➤ When indices are used with spelled-out element names, separate the name of the element and the index with a space. copper (111) rhenium (010) a gold (111) substrate on silicon (111) surfaces the silver (110) surface ➤ However, when indices are used with element symbols, close up the element symbol to the index. Au(210) CdTe(100) Cu(111) GaAs(100) Rh(010) Si(400) an iodine-modiﬁed Ag(111) electrode the Ag(110) surface Chapter 13: Conventions in Chemistry ➤ 269 Types of Crystal Lattices bcc ccp fcc hcp body-centered cubic cubic close-packed face-centered cubic hexagonal close-packed Symmetry Operations and Structural Point Groups ➤ Use italic type for the letters in symmetry operations and structural point groups. The symbols (Schoenﬂies) are as follows: E, identity; C, cyclic; D, dihedral; T, tetrahedral; O, octahedral; I, icosahedral; S, rotation–reﬂection; and σ, mirror plane. Align subscripts and superscripts. C1 Ci Cs C2 C 23 C 24 C∞ C2v C3v C4v C∞v C2h C3h D2d (Vd) D3d D4d D2h (Vh) D3h D4h D∞h Ih Oh (Kh) S3 S4 2S6 S8 σ 2σv 3σv 4σv 3σd σh Td Crystallographic Point Groups ➤ Use arabic numerals or combinations of numerals and the italic letter m to designate the 32 crystallographic point groups (Hermann–Mauguin). The number is the degree of the rotation, and m stands for mirror plane. Use an overbar to indicate rotation inversion. 1 m 2/m mm2 mmm 4mm 32 622 6/mmm 43m m3m Space Groups ➤ Designate space groups by a combination of unit cell type and point group symbol, modiﬁed to include screw axes and glide planes (Hermann–Mauguin); 230 space groups are possible. Use italic type for conventional types of unit cells (or Bravais lattices): P, primitive; I, body-centered; A, A-face-centered; B, B-facecentered; C, C-face-centered; F, all faces centered; and R, rhombohedral. 270 ➤ The ACS Style Guide Pnma C2/c Pbcn I41/a Fd3m Pnn2 P43212 Fm3m R3m Cmc21 P1 Fdd2 Aba2 I4/mmm Crystallographic Information File A description of the Crystallographic Information File, CIF, is included in Appendix 13-2. Chirality ➤ Use italic type for certain chirality symbols and symmetry site terms. A C CU DD anticlockwise clockwise cube dodecahedron OC TP TPR TPY octahedron trigonal phase trigonal prism trigonal pyramid These symbols are often combined with coordination numbers and position designations for stereochemical descriptors (e.g., OC-6-11′). ➤ In chemical names, use (R) and (S), with designated locants when applicable, as preﬁxes to designate absolute conﬁguration. (R)-hydroxyphenylacetic acid (S)-2,3-dihydroxypropanoic acid (1S,2S,4R)-trichloro-1,2,4-trimethylcyclohexane ➤ Indicate optical rotation by plus and minus signs in parentheses and hyphen- ate them to the chemical name. (±)-4-(2-aminopropyl)phenol (+)-glucose (–)-tartaric acid ➤ Use small capital letters d and l for absolute conﬁguration with amino acids and carbohydrates. β-d-cellotetraose d-allothreonine d-glucose d-valine dl-leucine hydroxy-dl-glutamic acid 5-hydroxy-l-lysine hydroxy-l-proline l-alanine l-alloisoleucine l-ascorbic acid l-phenylalanine Chapter 13: Conventions in Chemistry ➤ 271 ➤ Use a hyphen between (+) or (–) and d or l. (–)-d-fructose (–)-d-glyceraldehyde (+)-l-phosphoglycerol Concentration ➤ Use square brackets enclosing an element symbol or formula to indicate its concentration in reactions and equations, but not in narrative text. correct [Mg2+] = 3×10–2 M The Mg concentration decreased with repeated washings. incorrect The [Mg] was found to be greater in the unwashed samples. ➤ Do not use square brackets to indicate concentration with a spelled-out name. [Ca2+] (not [calcium]) [NaCl] (not [sodium chloride]) ➤ Do not use italic type for the chemical concentration unit M (molar, moles per cubic decimeter, moles per liter) or the unit N (normal). Use italic type for the unit m (molal, moles per kilogram). Use a space between the number and these abbreviations, that is, on each side of these abbreviations. 8 M urea 1 mM EDTA 6 N HCl 2.0 m NaOH ➤ When concentration is given as percentage, use the percent sign closed up to the number. 20% H2SO4 90% acetonitrile/10% water ➤ Generally, the negative logarithm of the hydrogen ion concentration is denoted by pH; the negative logarithm of the hydroxide ion concentration is denoted by pOH. Use a space to separate pH or pOH and the number. Use 272 ➤ The ACS Style Guide roman type for pH and pOH; always use lowercase for “p”; always capitalize “H” and “OH”. Solutions were titrated to pH >11. The UV spectra were measured at pH 6. A pOH of <12 was acceptable. Chemical Reactions ➤ Short chemical reactions may be run into text or they may be displayed and numbered, if numbering is needed. Long chemical reactions should be displayed separately from the text. The sequential numbering system used may integrate both chemical and mathematical equations, or separate sequences using different notations may be used for different types of equations (e.g., eqs 1–3 could be used for a set of chemical reactions and eqs I–III could be used for a set of mathematical equations). The use of lettering, rather than numbering, sequences is also acceptable. Cr(CO)4 + CO → Cr(CO)5 (1) NH3 + HCOOH → NH2CHO + H2O (2) (C6H5)2P–P(C6H5)2 → 2(C6H5)2P (3) Fe(CO)5 + OCH3– → Fe(CO)4(CO2CH3)– (4) • ➤ Many kinds and combinations of arrows can be used. For example, two full arrows in opposite directions (O) indicate a reaction that is proceeding in both directions. Two arrows with half heads in opposite directions (s) indicate a reaction in equilibrium. A single arrow with heads on both sides (↔) indicates resonance structures, not a reaction. ➤ Specify the number of each species (molecules, atoms, ions, etc.) of reactants and products by a numeral written on the line and closed up to the symbol. 2Al + 6NaOH → 2Na3AlO3 + 3H2 (5) ➤ To indicate the aqueous, solid, liquid, or gas state, use the appropriate abbreviations on the line, in parentheses, and with no space preceding them. Ag(s) + H+(aq) + Cl–(aq) → AgCl(s) + ½H2(g) (6) 4FeS(s) + 7O2(g) → 2Fe2O3(s) + 4SO2(g) (7) ➤ Indicate reaction conditions and catalysts over and under the arrow in a smaller type size. The Greek capital letter delta indicates heat; hν indicates light, where h is Planck’s constant and the Greek letter nu is the photon frequency. Chapter 13: Conventions in Chemistry ➤ 273 PhS− hν → PhSi + e− C3H8 (g) + 5O2 (g) ∆ → 3CO2 (g) + 4H2O(g) t or Pd → RCH2 NH2 RC ≡ N + 2H2 P KMnO 4 2H2O + CH3C(CH3 )=C(CH3 )CH3 HSO  → 2CH3C(=O)CH3 + 2H2 ,∆ 2 4 + H (C2H5 )2 C=O + 2CH3OH 125  → (C2H5 )2 C(OCH3 )2 + H2O °C ➤ Specify nuclear reactions according to the following scheme:  incoming  initial nuclide  particle(s) ,  or qu uanta  outgoing   particle(s)  final nuclide or quanta  examples 14N(α,p)17O 59Co(n,γ)60Co 23Na(γ,3n)20Na 31P(γ,pn)29Si ➤ Treat chemical equations that include structures with rings as illustrations. They are discussed in Chapter 17. ➤ Abbreviate reaction types with capital roman letters and arabic numerals. SN1 E1 SRN1 SN2 E2 SRN2 ﬁrst- and second-order nucleophilic substitution, respectively ﬁrst- and second-order elimination, respectively ﬁrst- and second-order radical nucleophilic substitution, respectively ➤ Subscripts denote a chemical process or reaction. ads at c dil dpl f fus imm mix r sol sub trs vap adsorption atomization combustion dilution displacement formation fusion immersion mixing reaction in general solution sublimation transition vaporization 274 ➤ The ACS Style Guide ➤ Certain superscripts are recommended. ‡ ′ E id ∞ ∗ °, & activated complex, transition state apparent excess quantity ideal inﬁnite dilution pure substance standard state Reporting Analytical Data There is no best way to present data. A presentation that is suitable for one paper or publication may be unsuitable for another. The following are examples of acceptable presentations of analytical data. These are not necessarily real examples; they may be combinations of data from two or more samples, intended to show various style possibilities. You need not deﬁne the abbreviations and symbols in the paper. Melting and Boiling Points mp 175.5 °C (lit.25 mp 175–176 °C) mp 225 °C dec bp 127 °C Abbreviations: mp, melting point; bp, boiling point; lit., literature value; and dec, decomposition. A full space is used between the number and the unit °C; the degree symbol is closed up to the C. A superscript number after “lit.” denotes the number of the reference. Speciﬁc Rotation [α]D20 + 25.4 (c 1.00, CHCl3) Abbreviations: α, speciﬁc rotation; D, the sodium D line or wavelength of light used for the determination; and the superscript number, temperature (°C) at which the determination was made. In parentheses: c stands for concentration; the number following c is the concentration in grams per 100 mL of solution; and last is the solvent name or formula. NMR Spectroscopy 1H NMR (400 MHz, CD OD, δ): 8.73 (s, 3H, –OCH ), 7.50 (s, 1H, CH), 7.15 (d, J 3 3 = 8.2 Hz, 1H, Ar H), 6–3 (br s, 5H, NH and NH2). Compound 5: 1H NMR (500 MHz, CDCl3, δ) 1.12 (t, J = 7.1 Hz, –CH2CH3, 3H), 3.34 (q, J = 7.1 Hz, –CH2CH3, 2H), 3.38 (t, J = 6.0 Hz, –CH2CH2OH, 2H), 3.72 (t, J = 6.0 Hz, –CH2CH2OH, 2H), 6.57 (dd, J = 8.7 Hz, Ar H, 2H). NMR (DMSO-d6, δ): 175.4 (C=O), 156.5 (C4), 147.4 (C6), 138.3 (C2), 110.5 (d, J = 11.3 Hz, C5), 52.3 (CH3), 28.4 and 28.8 (C7). 13C Chapter 13: Conventions in Chemistry ➤ 275 C NMR (DMSO-d6, δ): 0.43 (2C), 27.56 (4C), 131.8 (1C), 161.9 (2C). 13 13 C NMR (CDCl3, 75.4 MHz): δ 213.50 (s, C-21), 178.27 (s, C-2), 168.69 (s, C-8), 164.61 (d, C-10), 119.67 (d, C-7), 52.45 (t, C-22), 38.95 (q, C-25). C NMR (C6D12, δ): 6.51 (s, C5Me5), 14.41 (d, J = 157 Hz, PMe3), 28.68 (s, Me), 105.1 (t, J = 3.7 Hz, C5Me5), 128.52 (s), 135.19 (br s), 212.56 (C=O). 13 If the experimental conditions have already been described elsewhere in the paper, they need not be repeated. NMR: 3.81, 2.56, and 2.12 ppm. Compound 27: NMR 5.14, 3.90, 2.67, and 1.88 ppm. Abbreviations: δ, chemical shift in parts per million (ppm) downﬁeld from the standard; J, coupling constant in hertz; and the multiplicities s, singlet; d, doublet; t, triplet; q, quartet; and br, broadened. Italicized elements or groups are those that are responsible for the shifts. IR Spectroscopy IR (KBr) νmax: 967 (Ti=O), 3270 cm–1 (NH). IR (KBr, thin ﬁlm) νmax (cm–1): 3017, 2953 (s, OH), 2855 (s), 2192, 1512, 1360, 1082, 887. IR (dry ﬁlm) νmax: 3324 (OH), 2973–2872 (CH, aliphatic), 1706 (C=O, ketone), 1595, 1437, 1289, 1184, 1048, 870, 756, 677 cm–1. IR: 2000, 2030, 2040, 2050 cm–1. IR (cm–1): 3130, 3066, 2964, 1654, 1500, 1371. Compound 6: IR 2910, 2487, 1972, 1564, 1190 cm–1. GC–FTIR νmax (cm–1): 2979 (w), 1400 (m), 1264 (s), 827 (vs). Abbreviations: νmax is the wavenumber of maximum absorption peaks in reciprocal centimeters, and the absorptions are w, weak; m, medium; s, strong; vw, very weak; vs, very strong; and br, broad. Mass Spectrometry MS m/z (relative intensity): 238.2058 (44.8%), 195.1487 (100%), 153.1034 (21.2%). GC–MS m/z (% relative intensity, ion): 202 (9, M + 4), 200 (32, M + 2), 198 (23, M+), 142 (35, M – 2CO), 321 (95, M – Me), 415 (M+ – Cl). HRMS–FAB (m/z): [M + H]+ calcd for C21H38N4O6S, 475.259; found, 475.256. EIMS (70 eV) m/z: M+ 420 (15), 241 (15), 201 (59), 135 (14), 69 (23). Abbreviations: m/z is the mass-to-charge ratio, M is the molecular weight of the molecule itself, M+ is the molecular ion, HRMS is high-resolution mass spectrometry, FAB is fast atom bombardment, and EIMS is electron-impact mass spectrometry. 276 ➤ The ACS Style Guide UV–Visible Spectroscopy UV (hexanes) λmax, nm (ε): 250 (1070). UV (CH3OH) λmax (log ε) 210 (3.33), 242 (sh, 3.02), 288 (sh, 2.21), 421 nm (3.16). Abbreviations: λmax is the wavelength of maximum absorption in nanometers; ε is the molar absorption coefﬁcient or molar absorptivity; and sh is the shoulder. The wavenumber, ν, in reciprocal micrometers, might also be given. Quantitative Analysis Anal. Calcd for C45H28N4O7: C, 62.47; H, 3.41; N, 6.78. Found: C, 61.80; H, 3.55; N, 6.56. All values are given as percentages. X-ray Diffraction Spectroscopy ➤ Separate the element and its spectral line by a space. Au LI Au LIII Cr K Cu Kα Cu Kβ Mo Kα Cu Kα radiation the Co K absorption edge the Ni K edge Citing ASTM, ANSI, and ISO Standards ASTM International, originally known as the American Society for Testing and Materials; ANSI, the American National Standards Institute; and ISO, the International Organization for Standardization, are organizations that set standards in a variety of areas. ➤ For ASTM standards, separate the letter and the number of the standard by a space. For ANSI standards, close up the letter and the number. astm D 3137 D 573 D 130 D 1660 DS 4B DS 64 DS 48A E 380-93 STP 1249 STP 169C STP 315I as described in ASTM Standard D 1223 ansi Z358.1-1990 Z88.2-1992 as noted in ANSI Standard H35.1M-1993 iso 14020 9000 ISO/DIS 14010 according to ISO Standard 11634 71.040 ➤➤➤➤➤ APPENDIX 13-1 Symbols for Commonly Used Physical Quantities Atoms and Molecules name Atomic mass Atomic mass constant Atomic number Decay constant Electron rest mass Electronic term Elementary charge (of a proton) g factor, g value Ionization energy Magnetogyric ratio Mass number Neutron number Nucleon number Planck constant Planck constant/2π Proton number Proton rest mass Rotational constants Rotational term Total angular momentum component Total term Unified atomic mass unit Vibrational quantum number Vibrational term symbol ma mu Z λ me Te e g E i, I γ A N A h  Z mp A, B, C F mj , mJ T mu v G si unit kg kg dimensionless s–1 kg m–1 C dimensionless J s–1·T–1 dimensionless dimensionless dimensionless J·s J·s dimensionless kg m–1 m–1 dimensionless m–1 kg dimensionless m–1 Chemical Kinetics name Boltzmann constant Energy of activation; Arrhenius or activation energy Half-life Photochemical yield Quantum yield symbol si unit k, kB J/K, J·K–1 E, Ea, EA t1/2 φ φ J/mol, J·mol–1 s dimensionless dimensionless 277 278 ➤ The ACS Style Guide Chemical Kinetics—Continued name Rate constant, ﬁrst order Rate constant, second order Rate of concentration change of substance B Rate of conversion Rate of reaction Relaxation time Scattering angle Standard enthalpy of activation Standard entropy of activation Standard Gibbs energy of activation Standard internal energy of activation Temperature, absolute Thermal energy Volume of activation symbol si unit k k s–1 mol–1·s–1 rB · ζ v τ θ ∆‡H°, ∆H‡ ∆‡S°, ∆S‡ ∆‡G°, ∆G‡ mol/(m3·s), mol·m–3·s–1 mol/s, mol·s–1 mol/(m3·s), mol·m–3·s–1 s rad J/mol, J·mol–1 J/(mol·K), J·mol–1·K–1 J/mol, J·mol–1 ∆‡U°, ∆U‡ T kT ∆‡V, ∆V‡ J/mol, J·mol–1 K J J/mol, J·mol–1 Electricity and Magnetism name symbol si unit Capacitance Charge density Conductance Conductivity Dielectric polarization Electric charge Electric current Electric current density Electric dipole moment Electric displacement Electric ﬁeld strength Electric potential Electric potential difference Electric resistance Electric susceptibility Electromagnetic moment Impedance Inductance Magnetic ﬁeld strength Magnetic ﬂux Magnetic ﬂux density Magnetic induction Magnetic moment Magnetic susceptibility C ρ G κ P Q I j p, µ D E V, φ U, ∆V, ∆φ R χe µ, m Z H H Φ B B M χ C/V, C·V–1, F C/m3, C·m–3 S S/m, S·m–1 C/m2, C·m–2 C A A/m2, A·m–2 C·m C/m2, C·m–2 V/m, V·m–1 V, J/C, J·C–1 V Ω dimensionless A·m2, J/T, J·T–1 Ω A/m, A·m–1, H A/m, A·m–1, H Wb T T A/m, A·m–1 dimensionless Chapter 13: Conventions in Chemistry Electricity and Magnetism—Continued name symbol Magnetization Permeability Permittivity Polarization (of a particle) Relative permeability Relative permittivity Resistance Resistivity Self-inductance Voltage M µ ε α µr εr R ρ L U, ∆V, ∆φ ➤ si unit A/m, A·m–1 H/m, H·m–1 F/m, F·m–1 m2·C·V–1 dimensionless dimensionless Ω Ω·m H V Electrochemistry name Charge number of an ion Conductivity Diffusion rate constant Electric current Electric current density Electric mobility Electrode potential Electrolytic conductivity Electromotive force (emf) Elementary charge Faraday constant Half-wave potential Ionic strength concentration basis molality basis Mass-transfer coefﬁcient Molar conductivity Reduction potential Standard electrode potential Standard electromotive force (emf) Surface charge density Transport number symbol si unit z κ kd I j u E κ E e F E1/2 dimensionless S/m, S·m–1 m/s, m·s–1 A A/m2, A·m–2 m2/(V·s), m2·V–1·s–1 V S/m, S·m–1 V C C/mol, C·mol–1 V Ic, I Im, I kd Λ E° E° E° σ t mol/m3, mol·m–3 mol/kg, mol·kg–1 m/s, m·s–1 S·m2/mol, S·m2·mol–1 V V V C/m2, C·m–2 dimensionless General Chemistry name Amount concentration Amount of substance Atomic weight Concentration Degree of dissociation symbol c n Ar c α si unit mol/m3, mol·m–3 mol dimensionless mol/m3, mol·m–3 dimensionless 279 280 ➤ The ACS Style Guide General Chemistry—Continued name Extent of reaction Mass fraction Molality Molar mass Molar volume Molarity Mole fraction Molecular weight Number concentration Number density of entities Number of entities Partial pressure of substance B Relative atomic mass Relative molecular mass Stoichiometric coefﬁcient Surface concentration Volume fraction symbol ζ w m, b M Vm M x Mr C, n C, n N pB Ar Mr ν Γ φ si unit mol dimensionless mol/kg, mol·kg–1 kg/mol, kg·mol–1 m3/mol, m3·mol–1 mol/L, mol·L–1 dimensionless dimensionless m–3 m–3 dimensionless Pa dimensionless dimensionless dimensionless mol/m2, mol·m–2 dimensionless Mechanics name Angular momentum Density Energy Force Gravitational constant Hamiltonian function Kinetic energy Lagrange function Mass Moment of force Moment of inertia Momentum Potential energy Power Pressure Reduced mass Relative density Speciﬁc volume Surface tension Torque Weight Work symbol L ρ E F G H Ek, K L m M I p Ep, V P P, p µ d v γ T G, W w, W si unit J·s kg/m3, kg·m–3 J N N·m2/kg2, N·m2·kg–2 J J J kg N·m kg·m2 kg·m/s, kg·m·s–1 J W Pa, N/m2, N·m–2 kg dimensionless m3/kg, m3·kg–1 N/m, N·m–1, J/m2, J·m–2 N·m N J Chapter 13: Conventions in Chemistry NMR Spectroscopy name Bohr magneton Bohr radius Chemical shift, δ scale Coupling constant (indirect) spin–spin direct (dipolar) reduced spin–spin Delay time Electron spin quantum component Electron spin quantum number Hyperﬁne coupling constant Larmor angular frequency Larmor frequency Magnetogyric ratio Nuclear magneton Nuclear spin quantum component Nuclear spin quantum number Orbital quantum number Orbital quantum number component Principal quantum number Quadrupole moment Relaxation time longitudinal transverse Shielding constant symbol µB, β a0 δ JAB DAB KAB τ ms, mS s, S a, A, T ωL νL γ µN MI I l, L ml, mL n Q, Θ T1 T2 σ si unit J/T, J·T–1 m dimensionless Hz Hz T2·J–1, N·A–2·m–3 s dimensionless dimensionless Hz s–1 Hz s–1·T–1 J/T, J·T–1 dimensionless dimensionless dimensionless dimensionless dimensionless C·m2 s s dimensionless Polymer Chemistry name Bulk modulus Complex permittivity Crack-tip radius Electrophoretic mobility Flory–Huggins interaction parameter Fracture strain Fracture stress Glass-transition temperature Modulus of elasticity Tensile strength Viscosity Volume fraction Yield stress Young’s modulus symbol si unit K ε∗ ρc µ χ γf, εf σf Tg E σ ν Vf σy E Pa F/m, F·m–1 m m2·V–1·s–1 dimensionless Pa K Pa Pa Pa·s dimensionless Pa Pa ➤ 281 282 ➤ The ACS Style Guide Radiation name Absorbance Absorption factor Angle of optical rotation Angular frequency Emissivity, emittance Frequency Linear decadic absorption coefﬁcient Molar decadic absorption coefﬁcient Molar refraction Radiant energy Radiant intensity Radiant power Refractive index Speed of light Stefan–Boltzmann constant Transmittance Wavelength Wavenumber (in a vacuum) symbol A α α ω ε ν a ε Rm Q, W I P n c σ T λ ν si unit dimensionless dimensionless dimensionless, rad s–1, rad/s, rad·s–1 dimensionless Hz m–1 m2/mol, m2·mol–1 m3/mol, m3·mol–1 J W/sr, W·sr–1 W dimensionless m/s, m·s–1 W/(m2·K4), W·m–2·K–4 dimensionless m m–1 Space and Time name symbol si unit Acceleration Area Cartesian space coordinates Characteristic time interval Circular frequency Diameter Frequency Height Length Position vector Radius Speed Thickness, distance Time Time constant Velocity Volume a A, S, AS x, y, z τ ω d ν, f h l r r v, u, w, c d, δ t τ v, u, w, c V m/s2, m·s–2 m2 m s s–1, rad/s, rad·s–1 m Hz m m m m m/s, m·s–1 m s s m/s, m·s–1 m3 Chapter 13: Conventions in Chemistry ➤ 283 Thermodynamics name Absolute activity Afﬁnity of a reaction Chemical potential Cubic expansion coefﬁcient Energy Enthalpy Entropy Fugacity Gas constant Gibbs energy Heat Heat capacity, molar Heat capacity at constant pressure Heat capacity at constant volume Helmholtz energy Internal energy Isothermal compressibility Joule–Thomson coefﬁcient Pressure, osmotic Pressure coefﬁcient Speciﬁc heat capacity Surface tension Temperature Celsius thermodynamic Viscosity Work symbol si unit λ A µ α E H S f R G q, Q Cm Cp Cv A U κ µ Π β c γ, σ dimensionless J/mol, J·mol–1 J/mol, J·mol–1 K–1 J J J/K, J·K–1 Pa J/(K·mol), J·K–1·mol–1 J J J/(K·mol), J·K–1·mol–1 J/K, J·K–1 J/K, J·K–1 J J Pa–1 K/Pa, K·Pa–1 Pa Pa/K, Pa·K–1 J/(K·kg), J·K–1·kg–1 J/m2, J·m–2, N/m, N·m–1 t, θ T η w, W °C K Pa·s J Transport Properties name Coefﬁcient of heat transfer Diffusion coefﬁcient Flux of a quantity x Heat ﬂow rate Kinematic viscosity Mass ﬂow rate Mass-transfer coefﬁcient Thermal conductivity Thermal diffusion coefﬁcient Thermal diffusivity Viscosity Volume ﬂow rate symbol h D Jx, J φ ν qm kd λ, k DT a η qv, V si unit W/(m2·K), W·m–2·K–1 m2/s, m2·s–1 varies W m2/s, m2·s–1 kg/s, kg·s–1 m/s, m·s–1 W/(m·K), W·m–1·K–1 m2/s, m2·s–1 m2/s, m2·s–1 Pa·s m3/s, m3·s–1 ➤➤➤➤➤ APPENDIX 13-2 The Crystallographic Information File Frank H. Allen The Crystallographic Information File (CIF) is the internationally agreed on standard ﬁle format for the exchange of crystallographic information. Most major journals now require that crystal structure data for small molecules and inorganic compounds, obtained by single-crystal and powder diffraction analyses, be deposited as electronic CIFs as part of the manuscript submission process. A related format, the macromolecular CIF, or mmCIF, has been developed for data deposition with the Protein Data Bank. The CIF (and mmCIF) standard is maintained by the International Union of Crystallography (IUCr), and full information and leading references can be found at www.iucr.org/iucr-top/cif/. Important sources of three-dimensional crystal structure data, including data in CIF or mmCIF format, are the following: • The Cambridge Crystallographic Data Centre produces the Cambridge Structural Database (http://www.ccdc.cam.ac.uk/products/csd/), which covers organic and metal-organic small-molecule crystal structures. • CRYSTMET (http://www.tothcanada.com/) contains data for metals, intermetallics, and alloys. • FIZ Karlsruhe produces the ICSD (http://www.ﬁz-informationsdienste. de/en/FG/Kristall/index.html), which contains information on inorganic crystal structures. • The Nucleic Acid Database (http://ndbserver.rutgers.edu/) contains data on oligonucleotides. • The Protein Data Bank (http://www.rcsb.org/pdb/) contains biological macromolecular structure data. CIF principles are simple. Every data item is represented by a unique data name followed by its associated data value. Data items are described in an electronic dictionary that deﬁnes meaning, usage, and (where appropriate) permitted values or ranges of values. Data names start with an underscore (underline) character, and data values can be any type of string (text, numeric, or mixed), ranging from a single character to many lines of text. Data values are delimited by spaces, double or single quotes, or pairs of lines beginning with a semicolon (to delimit 284 Chapter 13: Conventions in Chemistry ➤ 285 multiline data items). Related data items, such as those that relate to an individual crystal structure, are grouped together in a data block. The start of a block is designated by the string data_ preﬁxing the name of the block, and the end of a block is recognized by another data_ record introducing a new block, or by the end of the ﬁle. A complete CIF may contain any number of data blocks, each reporting an individual crystal structure, and these may be preceded by a data block containing items (such as author names and contact details) that are common for all structures in the complete CIF. These basic principles, together with the data names in the CIF standard, make the CIF human readable, as illustrated below: data_structure_1 _cell_length_a _chemical_formula_moiety _publ_contact_author ; Dr J. Smith Department of Chemistry University of Nowhere Nowhere Anystate 20761 USA ; 5.959(1) ‘C23 H36 O7’ If a data name is preceded by loop_, then a series of values can be associated with that name, e.g., _symmetry_equiv_pos_as_xyz. A series of data values can also be grouped together under different data names using the loop_ construct, as in the example below, which shows a loop containing the atom labels and x,y,z-coordinates for four atoms. Here, the data names can be regarded as the column headings in a conventional printed table. loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z I1 0.26639(7) 0.61557(3) 0.94292(3) I2 0.64548(7) 0.364889(3) 0.56299(3) P3 0.0438(2) 0.27607(11) 0.74432(13) O1 -0.0989(7) 0.2488(3) 0.6619(4) The crystallographic part of a CIF is generated automatically by the software package used for structure refinement. However, the software can only output data items that it knows about, i.e., those items that are input to or are generated by the refinement process, or which can be generated reliably from these data. This is seldom sufﬁcient for journal submission, where additional data, such as author names and contact details, and other chemical or crystal property 286 ➤ The ACS Style Guide information are almost always required. Because these additional requirements will vary from journal to journal, authors should consult the author guidelines for the journal of their choice to ensure that they submit ﬁles that conform to the publisher’s requirements. Although the CIF can be edited using standard text editors, this is not recommended because the strict syntax, if broken in any small way, renders the ﬁle unreadable by application software. To solve the editing issue, a number of stand-alone CIF editors have been written. For example, the enCIFer program is available for free download from the Cambridge Crystallographic Data Centre Web site (http://www.ccdc.cam.ac.uk). The program will handle single-block or multiblock CIFs and has a graphical interface that permits the following: • location, display, and correction of syntax or format violations using the current CIF dictionary; • spreadsheet representation of looped data items; • editing and/or addition of individual or looped data items; • addition of certain standard information (basic bibliographic and/or property information) via two data entry wizards; and • three-dimensional visualization of the structure(s) contained in the CIF. The IUCr Web site (http://www.iucr.org/iucr-top/cif/) lists other software that can be used to manipulate or visualize CIF content. Most importantly, they maintain a Web-based service that provides a classiﬁed validation report on any format-compliant CIF. This service can be accessed at http://checkcif.iucr.org/. CheckCIF reports can be lengthy, but it is wise to scan them carefully, particularly the most serious Class A alerts. Journal editors and their referees will often indicate the types of alerts that they would normally expect to be ﬁxed by the authors before publication. ➤➤➤➤➤ CHAPTER 14 References Janet S. Dodd, Leah Solla, and Paula M. Bérard T his chapter presents style conventions for citing references within a manuscript and for listing complete reference citations. Many of the references in the examples were created to illustrate a style point under discussion; they may not be real references. Citing References in Text In ACS publications, you may cite references in text in three ways: 1. By superscript numbers, which appear outside the punctuation if the citation applies to a whole sentence or clause. Oscillation in the reaction of benzaldehyde with oxygen was reported previously.3 2. By italic numbers in parentheses on the line of text and inside the punctuation. The mineralization of TCE by a pure culture of a methane-oxidizing organism has been reported (6). 3. By author name and year of publication in parentheses inside the punctuation (known as author–date). The primary structure of this enzyme has also been determined (Finnegan et al., 2004). In ACS books, all three of these systems are used, depending on the subject matter and series. Table 14-1 lists the referencing systems used by the ACS journals currently in print. Copyright 2006 American Chemical Society 287 288 ➤ The ACS Style Guide Table 14-1. ACS Periodicals, with Referencing Style, CASSI Abbreviation, and 2006 Volume Number Name as Registered in the U.S. Patent and Trademark Ofﬁce Referencing Stylea CASSI Abbreviation 2006 Vol. Accounts of Chemical Research 1 Acc. Chem. Res. 39 ACS Chemical Biology 2 ACS Chem. Biol. 1 Analytical Chemistry 1 Anal. Chem. 78 review issues 2 Biochemistry 2 Biochemistry 45 Bioconjugate Chemistry 2 Bioconjugate Chem. 17 Biomacromolecules 1 Biomacromolecules Biotechnology Progress 2 Biotechnol. Prog. 22 Chemical & Engineering News 7 Chem. Eng. News 84 Chemical Research in Toxicology 2 Chem. Res. Toxicol. 19 Chemical Reviews 1 Chem. Rev. Chemistry of Materials 1 Chem. Mater. 106 Crystal Growth & Design 1 Cryst. Growth Des. Energy & Fuels 1 Energy Fuels 20 Environmental Science & Technology 2 Environ. Sci. Technol. 40 Industrial & Engineering Chemistry Research 1 Ind. Eng. Chem. Res. 45 Inorganic Chemistry 1 Inorg. Chem. 45 Journal of Agricultural and Food Chemistry 2 J. Agric. Food Chem. 54 18 6 Journal of the American Chemical Society 1 J. Am. Chem. Soc. 128 Journal of Chemical and Engineering Data 1 J. Chem. Eng. Data 51 Journal of Chemical Information and Modeling 1 J. Chem. Inf. Model. 46 Journal of Chemical Theory and Computation 1 J. Chem. Theory Comput. Journal of Combinatorial Chemistry 1 J. Comb. Chem. Journal of Medicinal Chemistry 1 J. Med. Chem. 49 Journal of Natural Products 1 J. Nat. Prod. 69 The Journal of Organic Chemistry 1 J. Org. Chem. 71 2 8 The Journal of Physical Chemistry A 1 J. Phys. Chem. A 110 The Journal of Physical Chemistry B 1 J. Phys. Chem. B 110 Journal of Proteome Research 1 J. Proteome Res. Langmuir 1 Langmuir 22 Macromolecules 1 Macromolecules 39 Molecular Pharmaceutics 1 Mol. Pharm. 3 Nano Letters 1 Nano Lett. 6 Organic Letters 1 Org. Lett. 8 Organic Process Research & Development 1 Org. Process Res. Dev. 10 Organometallics 1 Organometallics 25 a 5 Reference style 1 uses superscript numbers, and 2 uses italic numbers in parentheses on the line of the text. Chapter 14: References ➤ 289 ➤ In all three systems, the author’s name may be made part of the sentence. In such cases, in the author–date system, place only the year in parentheses. The syntheses described by Fraser8 take advantage of carbohydrate topology. Jensen (3) reported oscillation in the reaction of benzaldehyde with oxygen. According to Harris (2003), drug release is controlled by varying the hydrolytic stability of the ester bond. ➤ With numerical reference citations, start with 1 and number consecutively throughout the paper, including references in text and those in tables, ﬁgures, and other nontext components. If a reference is repeated, do not give it a new number; use the original reference number. ➤ Whenever authors are named, if a reference has two authors, give both names joined by the word “and”. If a reference has more than two authors, give only the ﬁrst name listed, followed by “et al.” Do not use a comma before et al.; always use a period after al. Allison and Perez12 Johnson et al. (12) (O’Brien and Alenno, 2005) (Bachrach et al., 2004) ➤ To cite more than one reference by the same principal author and various coauthors in one of the numerical citation systems, use the principal author’s name followed by “and co-workers” or “and colleagues”. Pauling and co-workers10,11 Cram and colleagues (27–29) ➤ When citing more than one reference at one place by number in one of the numerical systems, list the numbers in ascending order and separate them by commas (without spaces as superscripts, with spaces on line), or if they are part of a consecutive series, use an en dash to indicate a range of three or more. in the literature2,5,8 were reported3–5,10 in the literature (2, 5, 8) were reported (3–5, 10) ➤ When citing more than one reference at one place by the author–date system, list them alphabetically according to the ﬁrst author’s name, followed by a comma and the year. Use a semicolon to separate individual references. (Axelrod, 2003; Cobbs and Stolman, 2005; Gerson et al., 2001) 290 ➤ The ACS Style Guide ➤ When citing more than one reference by the same author at one place by the author–date system, do not repeat the name. List the name followed by the year of each of the references in ascending order; separate the years by commas. If an author has more than one reference in the same year, add lowercase letters to the years to differentiate them. Add letters to all of the years, for example, 2005a, 2005b, etc., not 2005, 2005a, etc. (The references in the list will need to be listed the same way, for example, 2005a, 2005b. (Trapani, 2003, 2005; Zillman, 2004) (Knauth, 2005a, 2005b) (Fordham, 2004; Fordham and Rizzo, 2004) ➤ Cite the reference in a logical place in the sentence. recent investigations (cite) other developments (cite) was reported (cite) as described previously (cite) previous results (cite) were demonstrated (cite) a molecular mechanics study (cite) Marshall and Levitt’s approach (cite) the procedure of Lucas et al. (cite) Style for Reference Lists Authors are responsible for the accuracy and completeness of all references. Authors should check all parts of each reference listing against the original document. A reference must include certain minimum data: • Periodical references must include the author names, abbreviated journal title, year of publication, volume number (if any), and initial page of cited article (the complete span is better). • Book references must include the author or editor names, book title, publisher, city of publication, and year of publication. • For material other than books and journals, sufﬁcient information must be provided so that the source can be identiﬁed and located. In lists, references always end with a period. Table 14-2 provides sample references for common reference types. Chapter 14: References ➤ 291 Periodicals recommended formats Author 1; Author 2; Author 3; etc. Title of Article. Journal Abbreviation Year, Volume, Inclusive Pagination. Author 1; Author 2; Author 3; etc. Journal Abbreviation Year, Volume, Inclusive Pagination. The journal Biochemistry is an exception. Consult this journal’s instructions to authors for the correct format. Author Name Field Include all author names in a reference citation. With multiple authors, separate the names from one another by semicolons. Always end the author ﬁeld with a period (exception: Biochemistry). List the names in inverted form: surname ﬁrst, then ﬁrst initial, middle initial, and qualiﬁers (Jr., II). Some publications list the ﬁrst 10 authors followed by a semicolon and et al.; check the guidelines. Cotton, F. A. Basconi, J.; Lin, P. B. Chandler, J. P., III; Levine, S. M. Schafer, F. W., Jr. Fishman, W., II. Farhataziz. (a single name is uncommon, but does occur; no period in Biochemistry) Inderjit; Fontana, M. J. (the ﬁrst author has a single name) Article Title Field Article titles are not essential in reference citations, but they are considered desirable to highlight the contents of a paper and facilitate location in reference libraries. Some ACS publications include the article title in journal references, and some do not; check the publication itself. Article titles are set in roman type without quotation marks and end with a period (or a question mark if that is part of the title). In ACS journals, capitalization follows that of the original publication; in other publications, the main words are capitalized. Caruso, R. A.; Susha, A.; Caruso, F. Multilayered Titania, Silica, and Laponite Nanoparticle Coatings on Polystyrene Colloidal Templates and Resulting Inorganic Hollow Spheres. Chem. Mater. 2001, 13, 400–409. Journal Abbreviation Field The journal name is an essential component of a periodical reference citation. Abbreviate the name according to the Chemical Abstracts Service Source Index 292 ➤ The ACS Style Guide Table 14-2. Common Types of References with Examples Reference Type Print Sources Journal article with article title without article title Nonscientific magazines and newspapers Books without editors See Pages Example 291 Klingler, J. Influence of Pretreatment on Sodium Powder. Chem. Mater. 2005, 17, 2755–2768. Klingler, J. Chem. Mater. 2005, 17, 2755–2768. Squires, S. Falling Short on Nutrients. The Washington Post, Oct 4, 2005, p H1. 291 299 300 with editors 300 Series publication cited as a book 306 cited as a journal 306 Meeting or conference, 307–308 full citation Theses 309–310 Patents 310–311 Government publications, U.S. Technical reports and bulletins 311–314 Material Safety Data Sheets Personal communications Online Periodicals Based on print editions 314 315 315–316 318 Le Couteur, P.; Burreson, J. Napoleon’s Buttons: How 17 Molecules Changed History; Jeremy P. Tarcher/Putnam: New York, 2003; pp 32–47. Almlof, J.; Gropen, O. Relativistic Effects in Chemistry. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1996; Vol. 8, pp 206–210. Puls, J.; Saake, B. Industrially Isolated Hemicelluloses. In Hemicelluloses: Science and Technology; Gatenholm, P., Tenkanen, M., Eds.; ACS Symposium Series 864; American Chemical Society: Washington, DC, 2004; pp 24–37. Puls, J.; Saake, B. ACS Symp. Ser. 2004, 864, 24–37. Garrone, E.; Ugliengo, P. In Structure and Reactivity of Surfaces, Proceedings of the European Conference, Trieste, Italy, Sept 13–20, 1988; Zecchina, A., Cost, G., Morterra, C., Eds.; Elsevier: Amsterdam, 1988. Mäckel, H. Capturing the Spectra of Silicon Solar Cells. Ph.D. Thesis, The Australian National University, December 2004. Sheem, S. K. Low-Cost Fiber Optic Pressure Sensor. U.S. Patent 6,738,537, May 18, 2004. Agriculture Fact Book 2000; U.S. Department of Agriculture, U.S. Government Printing Office: Washington, DC, 2000. Tschantz, B. A.; Moran, B. M. Modeling of the Hydrologic Transport of Mercury in the Upper East Fork Poplar Creek (UEFPC) Watershed; Technical Report for Lockheed Martin Energy Systems: Bethesda, MD, September 2004. Titanium Dioxide; MSDS No. T3627; Mallinckrodt Baker: Phillipsburg, NJ, Nov 12, 2003. Henscher, L. X. University of Minnesota, Minneapolis, MN. Personal communication, 2001. Fine, L. Einstein Revisited. J. Chem. Educ. [Online] 2005, 82, 1601 ff. http://jchemed.chem.wisc.edu/Journal/ Issues/2005/Nov/abs1601.html (accessed Oct 15, 2005). Published in advance of 318–319 Pratt, D. A.; van der Donk, W. A. Theoretical Investigations into the print issue Intermediacy of Chlorinated Vinylcobalamins in the Reductive Dehalogenation of Chlorinated Ethylenes. J. Am. Chem. Soc. [Online early access]. DOI: 10.1021/ja047915o. Published Online: Dec 8, 2004. http://pubs.acs.org/cgi-bin/asap.cgi/ jacsat/asap/html/ja047915o.html (accessed Dec 8, 2004). Continued on next page Chapter 14: References ➤ 293 Table 14-2. Common Types of References with Examples—Continued Reference Type See Pages Example Retrieved from a database provider 318 Published only electronically 319 From preprint servers 319 Hallet, V. Scanning the Globe for Organic Chemistry. U.S. News and World Report [Online], April 19, 2004, p 59. Business Source Premier. http://www.epnet.com/academic/ bussourceprem.asp (accessed April 24, 2005). Zloh, M.; Esposito, D.; Gibbons, W. A. Helical Net Plots and Lipid Favourable Surface Mapping of Transmembrane Helices of Integral Membrane Proteins: Aids to Structure Determination of Integral Membrane Proteins. Internet J. Chem. [Online] 2003, 6, Article 2. http://www.ijc.com/articles/ 2003v6/2/ (accessed Oct 13, 2004). Ward, D. W.; Nelson, K. A. Finite Difference Time Domain (FDTD) Simulations of Electromagnetic Wave Propagation Using a Spreadsheet. 2004, arXiv:physics/0402096. arXiv.org e-Print archive. http://arxiv.org/abs/physics/0402096 (accessed Oct 13, 2004). Online books without editors with editors Online encyclopedias Other Online Sources General Web sites Electronic lists and newsgroups Electronic mail messages CD-ROMs and DVDs periodicals books 319–320 Tour, J. M. Molecular Electronics: Commercial Insights, Chemistry, Devices, Architecture and Programming [Online]; World Scientific: River Edge, NJ, 2003; pp 177–180. http://legacy. netlibrary.com/ebook_info.asp?product_id=91422&piclist =19799,20141,20153 (accessed Nov 7, 2004). 320 Oleksyn, B. J.; Stadnicka, K.; Sliwinski, J. Structural Chemistry of Enamines: A Statistical Approach. In The Chemistry of Enamines [Online]; Rappoport, Z., Ed.; The Chemistry of Functional Groups; Patai, S., Rappoport, Z., Series Eds.; Wiley & Sons: New York, 1994; Chapter 2, pp 87–218. http://www3.interscience.wiley.com/cgi-bin/ summary/109560980/SUMMARY (accessed April 24, 2005). 320 Alkanolamines from Nitro Alcohols. Kirk-Othmer Encyclopedia of Chemical Technology [Online]; Wiley & Sons, Posted March 14, 2003. http://www.mrw.interscience.wiley.com/kirk/ articles/alkaboll.a01/frame.html (accessed Nov 7, 2004). 320–321 ACS Publications Division Home Page. http://pubs.acs.org (accessed Nov 7, 2004). 322 Chemical Information List Server, CHMINF-L@iubvm.ucs. indiana.edu (accessed Oct 13, 2004). Computational Chemistry List, solvent discussion in archived messages of September 2003, chemistry@ccl.net (accessed Nov 10, 2004). 322 Solla, L. R. Cornell University, Ithaca, NY. Personal communication, 2005. 322 Fleming, S. A.; Jensen, A. W. Substitutent Effects on the Photocleavage of Benzyl–Sulfur Bonds. Observation of the “Meta” Effect. J. Org. Chem. [CD-ROM] 1996, 61, 7044. 322–323 Green Chemistry: Meeting Global Challenges [DVD]; American Chemical Society: Washington, DC, 2003. 294 ➤ The ACS Style Guide (CASSI), and italicize it. One-word journal names are not abbreviated (e.g., Biochemistry, Macromolecules, Nature, Science). No punctuation is added to end this ﬁeld; thus, a period will be there with an abbreviation but not with a spelled-out word. CASSI and its quarterly supplements provide an extensive list of recommended journal abbreviations. Appendix 14-1 lists CASSI abbreviations for more than 1000 of the most commonly cited journals. ACS publication names, their abbreviations, and their volume numbers for 2006 are given in Table 14-1. Note that, in some cases, the word “the” is part of the title. Sometimes journal names change. Authors should use the abbreviation of the journal title that was in use at the time the article was published. CASSI lists the journal titles and the range of years during which the title was being used. Information Found in CASSI Entries are arranged in CASSI alphabetically according to the abbreviated form of the title. Abbreviations are based on the standards of the International Organization for Standardization (ISO). Recommended abbreviations are indicated in boldface type. See Appendix 14-2 for a sample CASSI entry with a description of each element in an entry. Using CASSI Abbreviations ➤ The boldface components of the publication title form the abbreviated title. Use a period after each abbreviation, and maintain the punctuation shown in CASSI. Journal of Polymer Science, Part A: Polymer Science J. Polym. Sci., Part A: Polym. Sci. ➤ Maintain the word spacing shown in CASSI, except for D.C., N.Y., U.K., U.S., and U.S.A. Analyst (Cambridge, U.K.) Anesth. Analg. (Hagerstown, MD, U.S.) Ann. N.Y. Acad. Sci. Proc. Natl. Acad. Sci. U.S.A. Science (Washington, DC, U.S.) ➤ Use a terminal period only if the last word of the periodical title is abbreviated. International Journal of Nanoscience Int. J. Nanosci. (last word is abbreviated; period is used) Journal of Controlled Release J. Controlled Release (last word is not abbreviated; no period is used) Chapter 14: References ➤ 295 ➤ If the periodical abbreviation in CASSI shows a hyphen with spaces on both sides, change the hyphen to an em dash closed up on each side. Annual Technical Conference - Society of Plastics Engineers Annu. Tech. Conf.—Soc. Plast. Eng. ➤ If a boldface n precedes the volume number in CASSI, use the abbreviation “No.” before the volume number in italics in the entry. British Medical Journal … n6372 1983 Br. Med. J. 1983, No. 6372. Include all the information shown for volume in italics, especially for references to government publications and reports. Los Alamos National Laboratory, [Report] LA (United States) … LA-14240-SR 2005 Los Alamos Natl. Lab., [Rep.] LA (U.S.) 2005, LA-14240-SR. Exceptions to the Rules of CASSI Abbreviations ➤ Strict rules for CASSI abbreviations can be modiﬁed for periodicals whose titles include multiple parts, sections, and series. abbreviation Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2005, 61, 99–102. acceptable variation The section title need not be named: Acta Crystallogr., Sect. C 2005, 61, 99–102. acceptable variation The section can be indicated by the volume number: Acta Crystallogr. 2005, C61, 99–102. ➤ For some periodicals whose CASSI abbreviation includes a place of pub- lication, you need not add the place of publication unless its omission would create ambiguity. If CASSI lists only one journal with a given main title, there is no ambiguity in omitting the place of publication. use not necessarily Clin. Chem. Nature Science Clin. Chem. (Washington, DC, U.S.) Nature (London, U.K.) Science (Washington, DC, U.S.) In contrast, omission of the place of publication would create ambiguity for different journals having the same main title. Transition Met. Chem. (Dordrecht, Neth.) Transition Met. Chem. (N.Y.) 296 ➤ The ACS Style Guide Year of Publication Field The year of publication is essential information in a periodical citation. The year is set in boldface type, followed by a comma in boldface type. Publication Volume Field The volume number is important information and is recommended for all periodical citations; it is essential for publications having more than one volume per year (such as the Journal of Chemical Physics). The volume number is set in italic type and is separated from the pagination information by a comma, which is set in italic type. ➤ For periodicals in which each issue begins with page 1, include issue information (either the number or the date) in the publication volume ﬁeld. Issue information is set in roman type, enclosed in parentheses, and spaced from the volume number, which it directly follows. issue number Mullin, R. Chem. Eng. News 2005, 83 (42), 7. date of issue Mullin, R. Chem. Eng. News 2005, 83 (Oct 17), 7. ➤ For publications that have supplements, the following form is recom- mended. Taylor, C. W.; Kumar, S. Eur. J. Cancer 2005, 40 (Suppl. 1), 781. Eur. J. Anaesthesiol. 2005, 22 (Suppl. S36), 1–35. ➤ For journals that have no volume numbers, include issue numbers, especially when the pagination of each issue begins with page 1. Use the following form. Note that the issue number is not italicized. Wills, M. R.; Savory, J. Lancet 1983, No. 2, 29. Pagination Field Pagination is an essential element of a reference citation. The complete page range is preferable, but initial page numbers are acceptable. ➤ In page spans, use all digits, closed up, with no commas or spaces. 2–15 44–49 103–107 1376–1382 2022–2134 11771–11779 Chapter 14: References ➤ 297 ➤ You may also indicate pagination in reference citations by “f ” or “ff ”, which mean “and following” page or pages, respectively. The f or ff is set in roman type and is spaced from the preceding number: 60 f (indicates page 60 and the page following—pages 60 and 61) 60 ff (indicates page 60 and pages following) 58–60 ff (indicates pages 58 through 60 and pages following—essentially the same as 58 ff except that the three pages enumerated contain the most pertinent information and other relevant information is scattered on the rest of the pages) ➤ The pagination ﬁeld may also include terms such as “and references therein” and similar expressions (especially in references to review articles). This phrase follows the page numbers and is not separated by a comma. Puskas, J. E.; Chan, S. W. P.; McAuley, K. B.; Shaikh, S.; Kaszas, G. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5394–5413 and references therein. ➤ Some publications use article numbering, rather than page numbering, where each article starts on page 1. Use the article number in the pagination ﬁeld. Brosset, C. Ark. Kemi, Mineral. Geol. 1945, 20A, No. 7. Use of Punctuation To Indicate Repeating Fields of Information The choice of what punctuation to use to indicate repeating ﬁelds of information depends on whether the publication will appear strictly in print or on the Web. For publications that will appear in both print and on the Web, use the rules for Web publications. ➤ In references that will appear only in print publications, use a semicolon, a comma, or a period to indicate repeating information. 1. Same authors in multiple publications: Chauvin, Y.; Gilbert, B.; Guibard, I. Vib. Spectrosc. 1991, 1, 299–304; J. Chem. Soc., Chem. Commun. 1990, 1715–1716. 2. Same authors in multiple publications, but with letters to separate the references (the semicolon from the previous example is changed to a period): (a) Schrock, R. R. Chem. Commun. 2003, 2389. (b) J. Mol. Catal. A 2004, 213, 21–30. 3. Same authors of multiple articles in the same journal: Lu, Y.; Pignatello, J. J. Environ. Sci. Technol. 2002, 36, 4553–4561; 2004, 38, 5853– 5862. When the year and volume are the same: Clay, S. A.; Koskinen, W. C. Weed Sci. 1990, 38, 74–80, 262–266. 298 ➤ The ACS Style Guide When the year is the same but the volumes are different: Badyal, R.; Fleissner, A. Chem. Phys. 2005, 317, 73–86; 2005, 316, 201–215. ➤ In references that will appear only in Web publications, provide complete references so that the references can be properly linked. If two or more references with the same authors are cited, it is not acceptable to combine them into a single reference. 1. Same authors in multiple publications: Chauvin, Y.; Gilbert, B.; Guibard, I. Vib. Spectrosc. 1991, 1, 299–304; Chauvin, Y.; Gilbert, B.; Guibard, I. J. Chem. Soc., Chem. Commun. 1990, 1715–1716. 2. Same authors in multiple publications, but with letters to separate the references: (a) Schrock, R. R. Chem. Commun. 2003, 2389. (b) Schrock, R. R. J. Mol. Catal. A 2004, 213, 21–30. 3. Same authors of multiple articles in the same journal: Lu, Y.; Pignatello, J. J. Environ. Sci. Technol. 2002, 36, 4553–4561; Lu, Y.; Pignatello, J. J. Environ. Sci. Technol. 2004, 38, 5853–5862. The same principle holds no matter what information is being repeated: provide each reference in its entirety. Do not use the Latin terms ibid. (in the same place) or idem (the same). References to Chemical Abstracts Use a semicolon to separate the periodical citation from a reference to its abstract (Chemical Abstracts). Mohamed, A. M.; Hawata, A.; El-Torgoman, M.; El-Kousy, S. M.; Ismail, A. E.; Øgaard Madsen, J.; Søtofte, I.; Senning, A. Eur. J. Org. Chem. 2002, 2039– 2045; Chem. Abstr. 2003, 138, 4195. Mloston, G.; Majchrazak, A.; Senning, A.; Søtofte, I. J. Org. Chem. 2002, 67, 5690–5695; Chem. Abstr. 2002, 137, 201289. Chemical Abstracts routinely contains more than one abstract per page. The method of distinguishing which abstract was being cited has changed over the years. Three variations are worth noting. 1. The column (two columns per page) in which the abstract occurs followed by a superscript number: Chem. Abstr. 1946, 40, 44638. (This is the eighth abstract in column 4463.) 2. The column (two columns per page) in which the abstract occurs followed by a letter, either on the line or superscript (generally italic): Chapter 14: References ➤ 299 Chem. Abstr. 1953, 47, 1167f. (This is abstract f in column 1167.) Chem. Abstr. 1947, 41, 571d. (This is abstract d in column 571.) 3. The abstract number itself followed by an online letter (roman), often a computer check character: Chem. Abstr. 1989, 110, 8215j. (This is abstract number 8215.) Special Situations ➤ You may treat Beilstein references as periodical references. Beilstein, 4th ed. 1950, 12, 237. ➤ Cite journals published in a foreign language either by the actual non-English title or by a translated form. Nippon Ishikai Zasshi or J. Jpn. Med. Assoc. Nouv. J. Chim. or New J. Chem. ➤ When citing an article printed in the English translation of a foreign-language journal, include reference to the original article, if possible, and use a semicolon to separate the two citations. Tarasov, Y. I.; Kochikov, I. V.; Kovtun, D. M.; Vogt, N.; Novosadov, B. K.; Saakyan, A. S. J. Struct. Chem. (Engl. Transl.) 2004, 45 (5), 778–785; Zh. Strukt. Khim. 2004, 45 (5), 822–829. ➤ Separate two or more companion publications with a semicolon. Clear, J. M.; Kelly, J. M.; O’Connell, C. M.; Vos, J. G. J. Chem. Res., Miniprint 2005, 3038; J. Chem. Res., Synop. 2005, 260. Nonscientiﬁc Magazines and Newspapers recommended format Author 1; Author 2; Author 3; etc. Title of Article. Title of Periodical, Complete Date, Pagination. For nonscientific magazines and other periodicals that are not abstracted by Chemical Abstracts Service, give the authors’ names in inverted form ending with a period, the article title in roman type with main words capitalized and ending with a period, the full magazine title in italic type followed by a comma in italic type, the complete date of the issue (see pp 160–161 about dates) ending with a comma, and the pagination. Squires, S. Falling Short on Nutrients. The Washington Post, Oct 4, 2005, p H1. 300 ➤ The ACS Style Guide Books Some ACS publications include the chapter title in book references, and some do not; check the publication itself. Also, consult the instructions to authors in Biochemistry for exceptions to the format presented here and elsewhere in this chapter. recommended formats for books without editors Author 1; Author 2; Author 3; etc. Chapter Title. Book Title, Edition Number; Series Information (if any); Publisher: Place of Publication, Year; Volume Number, Pagination. Author 1; Author 2; Author 3; etc. Book Title; Series Information (if any); Publisher: Place of Publication, Year; Volume Number, Pagination. When a book has authors and no editors, it means either that the entire book was written by one author or that two or more authors collaborated on the entire book. Le Couteur, P.; Burreson, J. Napoleon’s Buttons: How 17 Molecules Changed History; Jeremy P. Tarcher/Putnam: New York, 2003; pp 32–47. Morris, R. The Last Sorcerers: The Path from Alchemy to the Periodic Table; Joseph Henry Press: Washington, DC, 2003; pp 145–158. recommended formats for books with editors Author 1; Author 2; Author 3; etc. Chapter Title. In Book Title, Edition Number; Editor 1, Editor 2, etc., Eds.; Series Information (if any); Publisher: Place of Publication, Year; Volume Number, Pagination. Author 1; Author 2; Author 3; etc. In Book Title, Edition Number; Editor 1, Editor 2, etc., Eds.; Series Information (if any); Publisher: Place of Publication, Year; Volume Number, Pagination. When a book has editors, it means that different authors wrote various parts of the book independently of each other. The word “In” before the book title indicates that the authors mentioned wrote only a part of the book, not the entire book. Holbrey, J. D.; Chen, J.; Turner, M. B.; Swatloski, R. P.; Spear, S. K.; Rogers, R. D. Applying Ionic Liquids for Controlled Processing of Polymer Materials. In Ionic Liquids in Polymer Systems: Solvents, Additives, and Novel Applications; Brazel, C. S., Rogers, R. D., Eds.; ACS Symposium Series 913; American Chemical Society: Washington, DC, 2005; pp 71–88. Almlof, J.; Gropen, O. Relativistic Effects in Chemistry. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1996; Vol. 8, pp 206–210. If the book as a whole is being referenced, the author names might not appear. Ionic Liquids in Polymer Systems: Solvents, Additives, and Novel Applications; Brazel, C. S., Rogers, R. D., Eds.; ACS Symposium Series 913; American Chemical Society: Washington, DC, 2005. Chapter 14: References ➤ 301 Advances in Inorganic Chemistry and Radiochemistry; Emeléus, H. J., Sharpe, A. G., Eds.; Academic: New York, 2001. Author Name Field ➤ Separate the names of multiple authors by semicolons, and always end the author ﬁeld with a period (except in Biochemistry). List names in inverted form: surname ﬁrst, then ﬁrst initial, middle initial, and qualiﬁers (Jr., II). ➤ If a book has no primary authors because each chapter was written by a different author, you may place the editor names in the author name ﬁeld (especially for lists in alphabetical order). Separate editor names by commas, and in this case, the period after the abbreviation Ed. or Eds. terminates the ﬁeld. Stocker, J. H., Ed. Chemistry and Science Fiction; American Chemical Society: Washington, DC, 1998. ➤ A book might have no named authors because it was compiled by a com- mittee or organization. These books are discussed under the section “Works Written by an Organization or a Committee”, p 307. Chapter Title Field Chapter titles are not essential, but they are considered desirable components in reference citations because they highlight the contents of a paper and facilitate its location in reference libraries. Chapter titles are set in roman type and end with a period. Puls, J.; Saake, B. Industrially Isolated Hemicelluloses. In Hemicelluloses: Science and Technology; Gatenholm, P., Tenkanen, M., Eds.; ACS Symposium Series 864; American Chemical Society: Washington, DC, 2004; pp 24–37. Book Title Field Book titles are essential elements in book reference citations. In general, book titles should not be abbreviated. They are set in italic type and are separated from the next ﬁeld of the reference by a semicolon, which is set in italic type. ➤ The edition number (in ordinal form) and the abbreviation “ed.” follow the book title, set off by an italic comma; they are set in roman type. The edition information is separated from the next ﬁeld of the reference by a semicolon. Reagent Chemicals, 10th ed.; ➤ When both authors and editors are given, use the word “In” (set in roman type) immediately before the title of the book to indicate that the cited authors wrote only part of the book. 302 ➤ The ACS Style Guide Hillman, L. W. In Dye Laser Principles with Applications; Duarte, F. J., Hillman, L. W., Eds.; Academic: New York, 1990; Chapter 2. Editor Name Field For books with editors, list the names of the editors, after title and edition information, in inverted form as described in the section “Author Name Field”, separated from one another by commas. The names are denoted as editors by including the abbreviation “Eds.” or “Ed.” after the ﬁnal name. The editor ﬁeld is set in roman type and ends with a semicolon (unless it is used in the author ﬁeld location). Lignocellulose Biodegradation; Saha, B. C., Hayashi, K., Eds.; ACS Symposium Series 889; American Chemical Society: Washington, DC, 2004. The Chemistry of the Atmosphere: Oxidants and Oxidation in the Earth’s Atmosphere; Bandy, A. R., Ed.; Royal Society of Chemistry: Cambridge, U.K., 1995. In books that have no primary authors, the names of the editors may appear in either the author name field (especially for lists in alphabetical order) or the editor name field. When the editor names appear in the author name field, they are separated by commas and the field ends with a period. Saha, B. C., Hayashi, K., Eds.; Lignocellulose Biodegradation; ACS Symposium Series 889; American Chemical Society: Washington, DC, 2004. Bandy, A. R., Ed. The Chemistry of the Atmosphere: Oxidants and Oxidation in the Earth’s Atmosphere; Royal Society of Chemistry: Cambridge, U.K., 1995. Publication Information Field The name of the publisher, place of publication, and year of publication are essential elements in a book reference. Name of Publisher Check the title page, front and back, for the publisher’s name and location. Names and addresses of publishers are also listed in Chemical Abstracts Service Source Index, 1907–2004 Cumulative, pp 21I–39I. ➤ Generally, do not abbreviate publishers’ names. American Chemical Society, not Am. Chem. Soc. or ACS American Ceramic Society, not Am. Ceram. Soc. exception You may use well-known acronyms or abbreviations created by the publishers themselves. AIChE or American Institute of Chemical Engineers ASTM or American Society for Testing and Materials IUPAC or International Union of Pure and Applied Chemistry Chapter 14: References ➤ 303 ➤ In some publisher’s names, words such as Co., Inc., Publisher, and Press are not essential. Academic Press: New York or Academic: New York ➤ Expanded names are also not essential. John Wiley & Sons or John Wiley or Wiley ➤ It is not necessary to repeat the publisher’s name for a book compiled by the organization that published it. CRC Handbook of Chemistry and Physics, 85th ed.; Boca Raton, FL, 2004. Place of Publication For the place of publication, give the city and state for U.S. cities or the city and country for all others. The country or state is not needed if the city is considered a major city in the world and could not be confused easily with other cities of the same name (e.g., London, Paris, New York, and Rome). Use the two-letter postal abbreviations (listed in Chapter 10) for states. Spell out names of countries unless they have standard abbreviations, such as U.K. for United Kingdom. Birmingham, U.K. Boca Raton, FL Cambridge, MA Cambridge, U.K. Chichester, U.K. Dordrecht, Netherlands Elmsford, NY Englewood Cliffs, NJ London New York Princeton, NJ Springﬁeld, IL Springﬁeld, MA Washington, DC Year of Publication In book references, the year is set in lightface (not bold) roman type, following the place of publication. Terminate the ﬁeld with a period or with a semicolon if further information is given. Gould, S. J. The Structure of Evolutionary Theory; Belknap Press: Cambridge, MA, 2002. Kline, R. B. Principles and Practice of Structural Equation Modeling, 2nd ed.; Guilford Press: New York, 2004. Volume and Pagination Field Volume Information ➤ The volume ﬁeld contains speciﬁc information, such as volume number and chapter number. Use the following abbreviations and spelled-out forms with the capitalization, spelling, and punctuation shown: Abstract Chapter 304 ➤ The ACS Style Guide No. Paper Part Vol. (for speciﬁc volumes, Vol. 4; Vols. 1, 2; Vols. 1 and 2; Vols. 3–5) vols. (for a number of volumes, 4 vols.) Annual Review of Physical Chemistry; Leone, S. R., McDermott, A. E., Paul, A., Eds.; Annual Reviews: Palo Alto, CA, 2005; Vol. 56. ➤ If a volume or part number refers to the volume or part of an entire series of books, this information is placed where a series number would normally appear and not in the volume ﬁeld for the speciﬁc book being cited. Wiberg, K. In Investigations of Rates and Mechanisms of Reactions; Lewis, E. S., Ed.; Techniques of Chemistry, Vol. VI, Part I; Wiley & Sons: New York, 1974; p 764. ➤ If the book or set of books as a whole is the reference, do not include individual volume information. McGraw-Hill Encyclopedia of Science and Technology, 9th ed.; McGraw-Hill: New York, 2002; 20 vols. Pagination Information ➤ If you are citing a chapter, the complete page range is best, but initial page numbers are acceptable. Pagination may also be indicated by “f ” or “ff ” notation (meaning “and following” page or pages, respectively). The f or ff is set in roman type and is spaced from the preceding number. These points are illustrated under the “Pagination Field” heading for periodicals. ➤ Pagination information is set in roman type and ends with a period, except when miscellaneous information follows it, in which case it should end with a semicolon (see the next section). Use the abbreviations “p” and “pp” to indicate single and multiple pages, respectively. p 57 p 93 f pp 48–51 pp 30, 52, 76 pp 30, 52, 76 ff pp 30, 52, and 76 pp 562–569 pp 562–9 (acceptable in journals) 2005; Vol. 2, p 35. 2004; pp 55–61. ➤ If the book as a whole is the reference, page numbers need not be given. Chapter 14: References ➤ 305 Miscellaneous Information If you wish to include additional information about a book that is important for the reader to know, you may add it at the end of the reference with or without parentheses, append it to the title in parentheses before the semicolon, or place it between the title and the publisher. AOCS. Ofﬁcial Methods and Recommended Practices of the American Oil Chemists’ Society; Link, W. E., Ed.; Champaign, IL, 1958 (revised 1973). Brown, H. C. The Nonclassical Ion Problem; Plenum: New York, 1977; Chapter 5 (with comments by P. v. R. Schleyer). Otsu, T.; Kinoshita, M. Experimental Methods of Polymer Synthesis (in Japanese); Kagakudojin: Kyoto, Japan, 1972; p 72. Tessier, J. Structure, Synthesis and Physical–Chemical Properties of Deltamethrin. In Deltamethrin Monograph; Tessier, J., Ed.; Roussel-Uclaf: Paris, 1982; pp 37–66; translated by B. V. d. G. Walden. Tessier, J. Structure, Synthesis and Physical–Chemical Properties of Deltamethrin. In Deltamethrin Monograph; Tessier, J., Ed.; Walden, B. V. d. G., Translator; Roussel-Uclaf: Paris, 1982. Volatile Compounds in Foods and Beverages; Maarse, H., Ed.; Marcel Dekker: New York, 1991; see also references therein. Special Situations ➤ Organic Syntheses collective volumes should be treated as books. Organic Syntheses; Wiley & Sons: New York, Year; Collect. Vol. No., Pagination. year collective volume no. 1941 1943 1955 1963 1973 1988 1990 1993 1998 2004 I II III IV V VI VII VIII IX X Organic Syntheses, Cumulative Indices for Collective Volumes I–VIII was published in 1995. Beginning with Volume 82, each volume of Organic Syntheses is planned to be published online on orgsyn.org in installments about every three months, with printed volumes appearing annually. ➤ For references to the Kirk-Othmer Encyclopedia, include the article title followed by a period, similar to the citation of a chapter title. 306 ➤ The ACS Style Guide Chloramines and Bromamines. Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Wiley & Sons: New York, 1993; Vol. 4, pp 931–932. Series Publications Publications such as book series that are periodical in nature but are not journals may be styled as either books or journals. CASSI lists every document abstracted and indexed by the Chemical Abstracts Service; hence, book titles are included and abbreviated. Key words to look for with these types of publications include “Advances”, “Methods”, “Progress”, and “Series”. recommended format for citation as a book Author 1; Author 2; Author 3; etc. In Title; Editor 1, Editor 2, Eds.; Series Title and Number; Publisher: Place of Publication, Year; Pagination. ➤ In book format, use the regular citation format for a book reference, but include information pertaining to the series. The series title is spelled out and set in roman type. Kebarle, P. In Techniques for the Study of Ion–Molecule Reactions; Saunders, W., Farrar, J. M., Eds.; Techniques of Chemistry Series 20; Wiley & Sons: New York, 1988; p 125. Lignocellulose Biodegradation; Saha, B. C., Hayashi, K., Eds.; ACS Symposium Series 889; American Chemical Society: Washington, DC, 2004. ➤ If a volume or part number is given for a series of books instead of a series number, cite this information where a series number would normally appear. Wiberg, K. In Investigations of Rates and Mechanisms of Reactions; Lewis, E. S., Ed.; Techniques of Chemistry, Vol. VI, Part I; Wiley & Sons: New York, 1974; p 764. ➤ As for any book, you may cite speciﬁc chapters. Puls, J.; Saake, B. Industrially Isolated Hemicelluloses. In Hemicelluloses: Science and Technology; Gatenholm, P., Tenkanen, M., Eds.; ACS Symposium Series 864; American Chemical Society: Washington, DC, 2004; pp 24–37. ➤ In journal format, the series title is used as a journal title, abbreviated accord- ing to CASSI and italicized, and the series number is used as a journal volume number. recommended format for citation as a journal Author 1; Author 2; Author 3; etc. Abbreviation Year, Volume, Pagination. Puls, J.; Saake, B. ACS Symp. Ser., 2004, 864, 24–37. Kebarle, P. Tech. Chem. (N.Y.) 1988, 20, 125. Chapter 14: References ➤ 307 Works Written by an Organization or a Committee An organization or a committee may be the author of a book or periodical article. Acronyms for very well known organizations may be used. It is not necessary to repeat the publisher’s name for a work compiled by the organization that published it. book format American Chemical Society, Committee on Analytical Reagents. Reagent Chemicals: Speciﬁcations and Procedures, 10th ed.; Washington, DC, 2006. World Health Organization. Pathology and Genetics of Tumours of the Head and Neck; Albany, NY, 2002; Vol. 9. periodical format International Union of Pure and Applied Chemistry, Physical Chemistry Division, Commission on Molecular Structure and Spectroscopy. Presentation of Molecular Parameter Values for Infrared and Raman Intensity Measurements. Pure Appl. Chem. 1988, 60, 1385–1388. IUPAC. Molecular Absorption Spectroscopy, Ultraviolet and Visible (UV/VIS). Pure Appl. Chem. 1988, 60, 1449–1460. Meetings and Conferences References to work presented at conferences and meetings must be treated on a case-by-case basis. At least three types of citations are possible: 1. Full citations of published abstracts and proceedings. The format resembles that of a book citation. 2. CASSI citations of published abstracts and proceedings. The format is that of a periodical citation. 3. References to oral presentations, posters, or demonstrations at technical meetings, possibly accompanied by handouts or brochures. These references contain no publication information. Full Citations recommended format Author 1; Author 2; Author 3; etc. Title of Presentation. In Title of the Collected Work, Proceedings of the Name of the Meeting, Location of Meeting, Date of Meeting; Editor 1, Editor 2, etc., Eds.; Publisher: Place of Publication, Year; Abstract Number, Pagination. The format resembles that of a book citation. The title field, however, includes additional information on the meeting title, location, and dates. The actual title 308 ➤ The ACS Style Guide of the book (collected work) is set in italic type and is separated from the meeting information by a comma. The information on meeting location is set in roman type, but it is not repeated if it is included in the book title. The entire field ends with a semicolon. Garrone, E.; Ugliengo, P. In Structure and Reactivity of Surfaces, Proceedings of the European Conference, Trieste, Italy, Sept 13–20, 1988; Zecchina, A., Cost, G., Morterra, C., Eds.; Elsevier: Amsterdam, 1988. Abstracts are slightly different in that they usually do not have editors. The word “in” is not used before the book title. Prasad, A.; Jackson, P. Abstracts of Papers, Part 2, 212th National Meeting of the American Chemical Society, Orlando, FL, Aug 25–29, 1996; American Chemical Society: Washington, DC, 1996; PMSE 189. When the phrase “Proceedings of ” is part of the reference, include the publisher and place of publication. When a society sponsors a meeting, the society is assumed to be the publisher. If the place of the meeting and the place of publication are the same, additional publisher and place information is not required. However, many organizations such as the ACS sponsor meetings in various cities. Harwood, J. S. Direct Detection of Volatile Metabolites Produced by Microorganisms. Proceedings of the 36th ASMS Conference on Mass Spectrometry and Allied Topics, San Francisco, CA, June 5–10, 1988. CASSI Citations Proceedings and abstracts of meetings and conferences are indexed in CASSI. The reference format follows that for periodicals. Abstr. Pap.—Am. Chem. Soc. 1989, 198. CASSI gives the number of a meeting in ordinal form. Convert this number to an italic cardinal number, and use it as the volume number in the citation, unless CASSI has already indicated another volume number. Journal format can be used for references to preprint papers. Jones, J.; Oferdahl, K. Natl. Meet.—Am. Chem. Soc., Div. Environ. Chem. 1989, 29 (2), ENVR 22 (or Paper 22). Material That Has No Publication Information recommended formats Author 1; Author 2; Author 3; etc. Title of Presentation (if any). Presented at Conference Title, Place, Date; Paper Number. List the data concerning the conference (name, place, and date) separated by commas and followed by a semicolon and the paper number (if any). The entire citation is set in roman type. Chapter 14: References ➤ 309 Zientek, K. D.; Eyler, J. R. Presented at the 51st ASMS Conference on Mass Spectrometry and Allied Topics, Montreal, Canada, June 8–12, 2003. Dizman, B.; Elasri, M. O.; Mathias, L. J. Presented at the 227th National Meeting of the American Chemical Society, Anaheim, CA, March 28–April 1, 2004; Paper POLY 229. Theses recommended formats Author. Title of Thesis. Level of Thesis, Degree-Granting University, Location of University, Date of Completion. References to theses should be as specific as practical, including, at a minimum, the degree-granting institution and date. Chandrakanth, J. S. Effects of Ozone on the Colloidal Stability of Particles Coated with Natural Organic Matter. Ph.D. Dissertation, University of Colorado, Boulder, CO, 1994. Mäckel, H. Capturing the Spectra of Silicon Solar Cells. Ph.D. Thesis, The Australian National University, December 2004. Kulamer, T. M.S. Thesis, Princeton University, 2004. Author Name Field Cite the name in inverted form: surname ﬁrst, then ﬁrst initial, middle initial, and qualiﬁers (Jr., II). End the ﬁeld with a period. Title Field Thesis titles are not essential, but they are informative. They are set in roman type and end with a period. Erickson, T. A. Development and Application of Geostatistical Methods to Modeling Spatial Variation in Snowpack Properties, Front Range, Colorado. Ph.D. Dissertation, University of Colorado, Boulder, CO, 2004. Moore, S. Synthesis and Pharmacology of Potential Site-Directed Therapeutic Agents for Cocaine Abuse. Ph.D. Thesis, Georgia Institute of Technology, Atlanta, GA, 2004. Thesis Level Field Work done at a master’s level is often called a thesis. Work toward the Ph.D. (doctor of philosophy) may be called a thesis or a dissertation, depending on the policy of the degree-granting institution. The following abbreviations are standard for U.S. degrees. Many variations exist for degrees from institutions of other countries. 310 ➤ The ACS Style Guide A.B., B.A., B.S. A.M., M.A., M.S., M.B.A. Ph.D., M.D. Coghill, S. M.S. Thesis, Northwestern University, Evanston, IL, 2004. Breton, J. C. Intégrales Multiples Stochastiques Poissonniennes. Ph.D. Dissertation, University of Lille, France, 2001. University Name and Location Field The name of the degree-granting university is the minimum requirement for an acceptable citation. You should also include the city and state or city and country. Use the two-letter postal abbreviations for states. Spell out names of countries unless they have standard abbreviations, such as U.K. for United Kingdom. Blättler, T. M. Covalent Immobilization of Poly(l-lysine)-g-poly(ethylene glycol) onto Aldehyde Plasma Polymer Coated Surfaces. Diploma Thesis, University of South Australia, 2004. Mohamed, M. Waterjet Cutting Up to 900 MPa. Ph.D. Thesis, University of Hannover, Germany, 2004. Date of Completion Field Indicate the date the thesis was completed by year only; month and year; or month, day, and year. Fleissner, C. Ph.D. Thesis, New York University, March 2003. Marshall, M. Ph.D. Thesis, University of California, San Francisco, CA, 2005. Stover, J. Ph.D. Dissertation, Harvard University, May 24, 2001. Patents recommended format Patent Owner 1; Patent Owner 2; etc. Title of Patent. Patent Number, Date. The minimum data required for an acceptable citation are the name(s) of the patent owner(s), the patent number, and the date. Ensure that the patent stage (Patent, Patent Application, etc.) is indicated and that the pattern of the number (e.g., spaces, commas, dashes) follows that of the original patent document. If possible, include the title and the Chemical Abstracts reference (preceded by a semicolon) as well. Sheem, S. K. Low-Cost Fiber Optic Pressure Sensor. U.S. Patent 6,738,537, May 18, 2004. Lenssen, K. C.; Jantscheff, P.; Kiedrowski, G.; Massing, U. Cationic Lipids with Serine Backbone for Transfecting Biological Molecules. Eur. Pat. Appl. 1457483, 2004. Chapter 14: References ➤ 311 Petrovick, P. R.; Carlini, E. Antiulcerogenic Preparation from Maytenus ilicifolia and Obtaintion Process. Br. Patent PI 994502, March 6, 1999. Langhals, H.; Wetzel, F. Perylene Pigments with Metallic Effects. Ger. Offen. DE 10357978.8, Dec 11, 2003; Chem. Abstr. 2005, 143, 134834. Shimizu, Y.; Kajiyama, H. (Kanebo, Ltd., Japan; Kanebo Synthetic Fibers, Ltd.). Jpn. Kokai Tokkyo Koho JP 2004176197 A2 20040624, 2004. Government Publications Publications of the U.S. government and those of state and local governments can be pamphlets, brochures, books, maps, journals, or almost anything else that can be printed. They may have authors or editors, who may be individuals, ofﬁces, or committees, or the author may not be identiﬁed. They are published by speciﬁc agencies, but they are usually (though not always) available through the Government Printing Ofﬁce rather than the issuing agency. To enable others to ﬁnd the publication, the American Library Association suggests that you include as much information as possible in the citation. The following are examples of the most commonly cited types of references. Publications of Federal Government Agencies recommended format Author 1; Author 2; etc. Chapter Title. Document Title; Government Publication Number; Publishing Agency: Place of Publication, Year; Pagination. The format resembles that of a serial publication in book format. Include as much information as possible. Gebhardt, S. E.; Thomas, R. G. Nutritive Value of Foods; Home and Garden Bulletin No. 72; U.S. Department of Agriculture, U.S. Government Printing Ofﬁce: Washington, DC, 2002. Agriculture Fact Book 2000; U.S. Department of Agriculture, U.S. Government Printing Ofﬁce: Washington, DC, 2000. Dey, A. N.; Bloom, B. Summary Health Statistics for United States Children: National Health Interview Survey, 2003; DHHS Publication PHS 2005-1551; Department of Health and Human Services, Centers for Disease Control and Prevention, National Center for Health Statistics, U.S. Government Printing Ofﬁce: Washington, DC, 2005. ISCORS Assessment of Radioactivity in Sewage Sludge: Modeling To Assess Radiation Doses; NUREG-1783; EPA 832-R-03-002A; DOE/EH-0670; ISCORS Technical Report 2004-03; Interagency Steering Committee on Radiation Standards, Sewage Sludge Subcommittee, U.S. Government Printing Ofﬁce: Washington, DC, 2005. 312 ➤ The ACS Style Guide Author Name Field Include all author names. With multiple authors, separate the names from one another by semicolons. Always end the author ﬁeld with a period. List the names in inverted form: surname ﬁrst, then ﬁrst initial, middle initial, and qualiﬁers (Jr., II). Some publications list the ﬁrst 10 authors followed by a semicolon and “et al.” Chapter Title Field Chapter titles are set in roman type and end with a period. Document Title Field Treat the formal title of the document as the title of a book. These titles are set in italic type and are separated from the next component of the reference by a semicolon, which is set in italic type. Government Publication Number Field The government publication number, also called an agency report number, is important because it is unique to the publication and because some indexing services provide access by these numbers. These numbers (or number–letter combinations) are usually printed somewhere on the cover or title page of the document and are sometimes identiﬁed as a “report/accession number”. Treat a report number the same as a series number; that is, it follows the book title, ends with a semicolon, and is set in roman type. Publishing Agency Field The publishing agency ﬁeld may take on added complexity in government publications. Often, the ofﬁce or agency issuing the report as well as the Government Printing Ofﬁce must be cited. The order is department or agency, administration or ofﬁce, and ﬁnally U.S. Government Printing Ofﬁce, all separated by commas and set in roman type. The ﬁeld ends with a colon. Place of Publication Field For the U.S. Government Printing Ofﬁce, it is always Washington, DC. The ﬁeld ends with a comma preceding the date of publication. Year of Publication Field The year of publication is set in roman type and ends with a semicolon if it is followed by pagination information. It ends with a period if it is the last ﬁeld. Pagination Field The page numbers are set in roman type and end with a period, unless miscellaneous material is appended to the reference. Chapter 14: References ➤ 313 Alternative Format Government agency references can also be given with CASSI abbreviations. In that case, the format is the same as for periodicals. Thompson, C. R.; Van Atta, G. R.; Bickoff, E. M.; Walter, E. D.; Livingston, A. L.; Guggloz, J. Tech. Bull.—U.S. Dep. Agric. 1957, No. 1161, 63–70. Other Federal Publications Federal Register The Federal Register is a periodical and is treated as such in citations. Agency for Toxic Substances and Disease Registry. Update on the Status of the Superfund Substance-Speciﬁc Applied Research Program. Fed Regist. 2002, 67, 4836–4854. U.S. Food and Drug Administration. Food Labeling: Health Claims and Label Statements for Dietary Supplements. Fed Regist. 1999, 65 (195), 59855–59857. Code of Federal Regulations Licensing of Government Owned Inventions. Code of Federal Regulations, Part 404, Title 37, 2005. Labeling Requirements for Pesticides and Devices. Code of Federal Regulations, Part 156, Title 40, 1998; Fed. Regist. 1998, 15, 7. U.S. Code The Public Health and Welfare. U.S. Code, Section 1396a, Title 42, 2000. U.S. Laws Treat the name of the law as a chapter title (roman, terminated with a period). No publisher name is needed. The number and date of the law are separated by a comma. If additional publication information is given, it is preceded by a semicolon. Domestic Quarantine Notices. Code of Federal Regulations, Section 301.10, Title 7, Vol. 5, 2005. Federal Insecticide, Fungicide, and Rodenticide Act. Public Law 92-516, 1972; Code of Federal Regulations, Section 136, Title 7, 1990. State and Local Government Publications recommended format Author 1; Author 2; etc. Chapter Title. Document Title; Publication Number or Type; Publishing Agency: Place of Publication, Date; Pagination. Annual Report 2004: Moving Forward; Santa Barbara County Air Pollution Control District: Santa Barbara, CA, 2005. 314 ➤ The ACS Style Guide Turner, B.; Powell, S.; Miller, N.; Melvin, J. A Field Study of Fog and Dry Deposition as Sources of Inadvertent Pesticide Residues on Row Crops; Report of the Environmental Hazard Assessment Program; California Department of Food and Agriculture: Sacramento, CA, November 1989. Technical Reports and Bulletins Technical reports and bulletins come in many forms. Examples of some of these have already been presented. Many are in-house publications, and some are government publications. Others are reports of work in progress. The publication itself may include a phrase alluding to its status as a technical report or technical bulletin, but it may also simply be called a report or bulletin. Include whatever information is available, following the format shown for the word “Report”, “Report No.”, etc. Document titles are set in italic type. recommended format Author 1; Author 2; etc. Title of Report or Bulletin; Technical Report or Bulletin Number; Publisher: Place of Publication, Date; Pagination. Tschantz, B. A.; Moran, B. M. Modeling of the Hydrologic Transport of Mercury in the Upper East Fork Poplar Creek (UEFPC) Watershed; Technical Report for Lockheed Martin Energy Systems: Bethesda, MD, September 2004. Fourth DELOS Workshop. Evaluation of Digital Libraries; Final Report to the National Science Foundation on Grant IIS-225626; Hungarian Academy of Sciences: Budapest, 2002. Data Sets Data sets are compilations of data, such as spectra or property tables. These data sets are often published serially as loose-leaf services, but the content is not always organized in chapters as in other serial publications. The citation of a serial data set should contain the title of the data set, the publisher, the place of publication, the date of the volume, the data entry number (as opposed to the data value), and the name of the ﬁgure or other identifying information. The page number can be included in the citation if page numbers are used in the index of the data set. References to data retrieved from a stand-alone database should cite the source as a computer program (for example, MDL CrossFire Commander, see p 323 f) or as an online reference book (for example, the Kirk-Othmer Encyclopedia of Chemical Technology, see p 305 f), with the data entry number or other identifying information included at the end of the citation. Data retrieved from an Internet-based database should cite the source as a Web site (see pp 316 ff). If the data retrieved are calculated data, also cite the software used for calculation (for example, ACD/Labs). Chapter 14: References ➤ 315 recommended format for printed data sets Title; Publisher: Place of Publication, Date; Data Entry Number, Figure Title or other identifying information. The Sadtler Standard Spectra: 300 MHz Proton NMR Standards; Bio-Rad, Sadtler Division: Philadelphia, PA, 1994; No. 7640 (1-Chloropentane). Material Safety Data Sheets Material Safety Data Sheets (MSDSs) are published by the company that manufactures the material covered on the sheet. Citations should include the title of the data sheet, which is the name of the material; the MSDS number; the manufacturing company; the location of the company; and the date on which the document was released. If the online version was used, the designation “Online” is included in brackets after the MSDS number, and the URL and date accessed are included at the end of the citation. recommended formats Title; MSDS Number; Manufacturing Company: Location of Company, Date. Title; MSDS Number [Online]; Manufacturing Company: Location of Company, Date. URL (accessed Month Day, Year). Titanium Dioxide; MSDS No. T3627; Mallinckrodt Baker: Phillipsburg, NJ, Nov 12, 2003. Acetic Anhydride; MSDS No. A0338 [Online]; Mallinckrodt Baker: Phillipsburg, NJ, Feb 18, 2003. http://www.jtbaker.com/msds/englishhtml/a0338.htm (accessed Nov 10, 2004). Unpublished Materials Material in any stage preceding actual publication falls under this general classiﬁcation, as do personal communications and work not destined for publication. recommended format for material intended for publication Author 1; Author 2; etc. Title of Unpublished Work. Journal Abbreviation, phrase indicating stage of publication. Various phrases indicating the stage of publication are acceptable in these references. ➤ For material accepted for publication, use the phrase “in press”. Tang, D.; Rupe, R.; Small, G. J.; Tiede, D. M. Chem. Phys., in press. ➤ For material intended for publication but not yet accepted, use “unpublished work”, “submitted for publication”, or “to be submitted for publication”. 316 ➤ The ACS Style Guide Chatterjee, K.; Visconti, A.; Mirocha, C. J. Deepoxy T-2 Tetraol: A Metabolite of T-2 Toxin Found in Cow Urine. J. Agric. Food Chem., submitted for publication, 2004. Nokinara, K. Duke University, Durham, NC. Unpublished work, 2003. As Gordon G. Hammes says in Chapter 1 of this book, Occasionally, the attribution of an idea or fact may be to a “private communication” of a colleague or fellow scientist. In such cases, permission must be obtained from the individual in question before the citation is made. Reference to unpublished material should be avoided if possible because it generally will not be available to interested readers. recommended format for material not intended for publication Author. Afﬁliation, City, State. Phrase describing the material, Year. Henscher, L. X. University of Minnesota, Minneapolis, MN. Personal communication, 2001. Heltman, L. R. DuPont. Private communication, 2003. Wagner, R. L. University of Utah, Salt Lake City, UT. Unpublished work, 2004. Messages sent by electronic mail are considered personal communications and are referred to as such. Electronic Sources Electronic media continue to develop rapidly in content, organization, and presentation of information. The conventions for citing electronic resources are evolving to reﬂect these changes, but the basic principles of citation remain the same: present enough documentation with enough clarity to establish the identity and authority of the source and direction for locating the reference. The guidelines stress consistency both in presentation of information and in reasons for exceptions. To date, much of the material available in electronic media corresponds to and/or is modeled after the traditional print-based sources discussed earlier in this chapter and should be cited according to those guidelines as appropriate. However, given the transient nature of electronic sources, it is important to provide additional documentation about the format or online location and the date the source was accessed. Internet Sources Internet sources include online editions of traditional sources such as periodicals and books available through Web technology; new collective sites of information, including Internet-based databases using Web, ﬁle transfer protocol (FTP), Chapter 14: References ➤ 317 and Telnet technologies; and electronic mailing lists and mail messages that may or may not use Web interfaces. Each source has an electronic address; for sources using the World Wide Web, this address is called the uniform resource locator (URL). As Web interfaces and supporting technologies evolve, direct addresses of items will often change to reﬂect new structures. Changing addresses can disrupt access to information sources that may still be available but at new locations and in modiﬁed formats. This issue can be resolved locally through use of persistent URLs. A persistent URL remains constant, but the actual location of a source is tracked through a local database that can be updated without disrupting the URL. Information sources can also be tracked globally through coordinated efforts such as the Digital Object Identiﬁer (DOI) system. Information providers register their sources, which are assigned unique and persistent DOIs. Each DOI is similar to a barcode that manages a complex proﬁle of multiple pieces, formats, locations, ownership rights, and interoperability features. The identity of and access to an electronic information source is maintained through its DOI regardless of changes in location, format, or publisher. The use of DOIs is spreading among publishers as an efﬁcient system to manage journal articles and other types of intellectual property on the Web. Further information about the DOI system can be found at http://www.doi.org (accessed April 13, 2005). CrossRef is an application of the DOI system that links online citations across publishers. The unique identiﬁcation and persistent location information in the DOI is packaged into an open URL that publishers and libraries can use to link to subscribed full-text content from reference lists. These links appear with citations in the reference lists of online articles and databases from several participating publishers. For the purposes of citation, reference style conventions continue to use the URL as the most direct route to the location of a source. DOIs are sometimes used by publishers in place of page numbers or article numbers and should be included in citations in this context. ➤ URLs can be long and complicated, and there are conventions for splitting an address between multiple lines; see Chapter 10 (pp 156–157) for guidelines on breaking URLs and e-mail addresses. Online Periodicals There are several types of periodicals online, including those based on print editions, electronic copies retrieved from databases, articles released online in advance of a full print issue, periodicals published only in electronic format, and article preprints posted in preprint servers. The reference styles for periodicals apply, with additional information concerning online location and accession date assigned as needed. As for print periodicals, article titles are desirable but not included in all ACS publications; check the publication itself. 318 ➤ The ACS Style Guide recommended format for online periodicals based on print editions Author 1; Author 2; Author 3; etc. Title of Article. Journal Abbreviation [Online] Year, Volume, Inclusive pagination or other identifying information. URL (accessed Month Day, Year). Currently, the majority of the articles retrieved from online publications are based on corresponding print versions. For these articles, the basic periodical reference style is used, but if the article has been viewed only in its electronic form, the designation “Online” is included in brackets after the journal abbreviation. Fine, L. Einstein Revisited. J. Chem. Educ. [Online] 2005, 82, 1601 ff. http://jchemed. chem.wisc.edu/Journal/Issues/2005/Nov/abs1601.html (accessed Oct 15, 2005). recommended formats for electronic copies of articles retrieved from a database provider Author 1; Author 2; Author 3; etc. Title of Article. Journal Abbreviation [Online] Year, Volume, Article Number or other identifying information. Database Provider. URL of top page (accessed Month Day, Year). Author 1; Author 2; Author 3; etc. Title of Article. Title of Periodical [Online], Complete Date, Pagination. Database Provider. URL of top page (accessed Month Day, Year). Electronic copies of periodicals, nonscientific magazines, or newspapers retrieved from subscription database services often provide only the original text but not the original formatting or the figures. For online articles provided as content in a subscription database, use the reference style for periodicals or nonscientific magazines as appropriate, and include the name of the database provider, the URL of the top page, and the date accessed. Hallet, V. Scanning the Globe for Organic Chemistry. U.S. News and World Report [Online], April 19, 2004, p 59. Business Source Premier. http://www.epnet. com/academic/bussourceprem.asp (accessed April 24, 2005). recommended format for articles published online in advance of print issues Author 1; Author 2; Author 3; etc. Title of Article. Journal Abbreviation [Online early access]. DOI or other identifying information. Published Online: Month Day, Year. URL (accessed Month Day, Year). Often, articles are ready for publication in advance of a full issue of a periodical. Several publishers offer these articles online up to weeks in advance of the print issue. They are identical to the corresponding print articles except that page numbers are often not yet available. Publishers market this service under different names; the ACS Publications Division labels them As Soon As Publishable (ASAP). For citation purposes, use the designation “Online early access” in brackets after the journal abbreviation in place of the publisher-specific term. Chapter 14: References ➤ 319 Also include the DOI or other identifying information, the online publication date, the URL, and the date accessed. Pratt, D. A.; van der Donk, W. A. Theoretical Investigations into the Intermediacy of Chlorinated Vinylcobalamins in the Reductive Dehalogenation of Chlorinated Ethylenes. J. Am. Chem. Soc. [Online early access]. DOI: 10.1021/ ja047915o. Published Online: Dec 8, 2004. http://pubs.acs.org/cgi-bin/asap. cgi/jacsat/asap/html/ja047915o.html (accessed Dec 8, 2004). recommended format for periodicals published only in electronic format Author 1; Author 2; Author 3; etc. Title of Article. Journal Abbreviation [Online] Year, Volume, Article Number or other identifying information. URL (accessed Month Day, Year). A periodical published only in electronic format may include additional electronic features, data, or commentaries. Use the reference style for periodicals, and include the direct URL of the article as well as the date accessed. Volume and page numbers are often not relevant. If they are not used, include the article number, DOI, or other identifying information. Zloh, M.; Esposito, D.; Gibbons, W. A. Helical Net Plots and Lipid Favourable Surface Mapping of Transmembrane Helices of Integral Membrane Proteins: Aids to Structure Determination of Integral Membrane Proteins. Internet J. Chem. [Online] 2003, 6, Article 2. http://www.ijc.com/articles/2003v6/2/ (accessed Oct 13, 2004). recommended format for articles retrieved from preprint servers Author 1; Author 2; Author 3; etc. Title of Article. Year, Article Number. Name of Repository. URL (accessed Month Day, Year). Ward, D. W.; Nelson, K. A. Finite Difference Time Domain (FDTD) Simulations of Electromagnetic Wave Propagation Using a Spreadsheet. 2004, arXiv:physics/0402096. arXiv.org e-Print archive. http://arxiv.org/abs/physics/0402096 (accessed Oct 13, 2004). Online Books Books published online generally correspond to printed versions, and the reference styles are similar. Online location and access date should always be included when citing online books. Reference works published online are often updated with new content, and the dates on which sections were posted or updated should also be included. recommended format for online books without editors Author 1; Author 2; Author 3; etc. Book Title [Online]; Series Information (if any); Publisher: Place of Publication, Year; Volume Number, Pagination. URL (accessed Month Day, Year). 320 ➤ The ACS Style Guide Tour, J. M. Molecular Electronics: Commercial Insights, Chemistry, Devices, Architecture and Programming [Online]; World Scientiﬁc: River Edge, NJ, 2003; pp 177–180. http://legacy.netlibrary.com/ebook_info.asp?product_id=91422& piclist=19799,20141,20153 (accessed Nov 7, 2004). recommended format for online books with editors Author 1; Author 2; Author 3; etc. Chapter Title. In Book Title [Online]; Editor 1, Editor 2, etc., Eds.; Series Information (if any); Publisher: Place of Publication, Year; Volume Number, Pagination. URL (accessed Month Day, Year). Oleksyn, B. J.; Stadnicka, K.; Sliwinski, J. Structural Chemistry of Enamines: A Statistical Approach. In The Chemistry of Enamines [Online]; Rappoport, Z., Ed.; The Chemistry of Functional Groups; Patai, S., Rappoport, Z., Series Eds.; Wiley & Sons: New York, 1994; Chapter 2, pp 87–218. http://www3. interscience.wiley.com/cgi-bin/summary/109560980/SUMMARY (accessed April 24, 2005). recommended format for online encyclopedias Article Title. Encyclopedia Title, edition [Online]; Publisher, Posted Online Posting Date. URL (accessed Month Day, Year). Alkanolamines from Nitro Alcohols. Kirk-Othmer Encyclopedia of Chemical Technology [Online]; Wiley & Sons, Posted March 14, 2003. http://www.mrw. interscience.wiley.com/kirk/articles/alkaboll.a01/frame.html (accessed Nov 7, 2004). Web Sites Aside from online periodicals and books, general Web sites containing a wide variety of information might need to be cited. Some sites are accessible by anyone, but many are accessible only by subscription. Reference styles for FTP and Telnet sites are similar to those for Web sites. Speciﬁc examples are given here for general Web sites and databases, stand-alone documents, unpublished conference proceedings, and electronic theses. recommended format for general web sites Author (if any). Title of Site. URL (accessed Month Day, Year), other identifying information (if any). Use the title found on the Web site itself; add the words “Home Page” for clarification when needed. Data retrieved from Internet-based databases should include a data entry number. Stand-alone databases should be cited as computer programs (see p 323). ACS Publications Division Home Page. http://pubs.acs.org (accessed Nov 7, 2004). Chemical Abstracts Service. STN on the Web. http://stnweb.cas.org (accessed Nov 7, 2004). International Union of Pure and Applied Chemistry Home Page. http://www. iupac.org/dhtml_home.html (accessed April 24, 2005). Chapter 14: References ➤ 321 Library of Congress Home Page. http://www.loc.gov (accessed April 24, 2005). Northern Illinois University. Department of Chemistry and Biochemistry Home Page. http://www.chembio.niu.edu (accessed Nov 7, 2004). Shefﬁeld Chemistry Software Archive (Macintosh). ftp://ftp.shef.ac.uk/pub/uni/ academic/A-C/chem (accessed April 24, 2005). U.S. Environmental Protection Agency. http://www.epa.gov (accessed Nov 7, 2004). recommended format for documents retrieved from institutional or agency web sites Author 1; Author 2; Author 3; etc. Title of Document, Year. Title of Site. URL (accessed Month Day, Year). If an article is contained within a large and complex Web site, such as that for a university or a government agency, the host organization and the relevant program or department should be identified before giving the direct URL of the article and accession date. Chou, L.; McClintock, R.; Moretti, F.; Nix, D. H. Technology and education: New wine in new bottles: Choosing pasts and imagining educational futures, 1993. Columbia University Institute for Learning Technologies Web site. http://www. ilt.columbia.edu/publications/papers/newwine1.html (accessed Aug 24, 2000). recommended format for online unpublished conference presentations Author 1; Author 2; etc. Title of Presentation. Presented at Conference Title [Online], Place, Date; Paper Number. Title of Site. URL (accessed Month Day, Year). Works presented at conferences or meetings can be cited in several formats, as discussed earlier in this chapter. Generally, published abstracts or proceedings can be cited as online books or as online periodicals. Materials from oral presentations, posters, or demonstrations that do not contain publication information should be cited as follows. Manly, S. Collective ﬂow with PHOBOS. Presented at the 20th Winter Workshop on Nuclear Dynamics [Online], Trelawny Beach, Jamaica, March 15–20, 2004. University of Rochester, DSpace Web site. http://hdl.handle.net/1802/228 (accessed Oct 13, 2004). recommended format for electronic theses Author. Title of Thesis. Level of Thesis [Online], Degree-Granting University, Location of University, Date of Completion. URL (accessed Month Day, Year). Lozano, P. C. Studies on the Ion-Droplet Mixed Regime in Colloid Thrusters. Ph.D. Thesis [Online], Massachusetts Institute of Technology, Cambridge, MA, January 2003. http://theses.mit.edu/Dienst/UI/2.0/Describe/0018.mit. etheses%2f2003-1 (accessed Nov 7, 2004). 322 ➤ The ACS Style Guide Electronic Lists and Newsgroups recommended format for electronic lists and newsgroups Mailing List or Newsgroup Name, other information, electronic address (accessed Month Day, Year). Chemical Information List Server, CHMINF-L@iubvm.ucs.indiana.edu (accessed Oct 13, 2004). Computational Chemistry List, solvent discussion in archived messages of September 2003, chemistry@ccl.net (accessed Nov 10, 2004). Molecular Diversity for Basic Research & Drug Discovery, mol-diversity@listserv. arizona.edu (accessed Nov 10, 2004). Electronic Mail Messages Whether the message was personal and sent only to you or whether it was posted in a newsgroup, it is not published. E-mail messages should be cited the same as any other personal communication. Include the year and the professional afﬁliation of the author. recommended format for electronic mail messages Author. Afﬁliation, City, State. Personal communication, Year. Solla, L. R. Cornell University, Ithaca, NY. Personal communication, 2005. CD-ROMs and DVDs The reference style for information published in CD-ROM or DVD format follows that for periodicals and books as appropriate, and the designation “CDROM” or “DVD” is included in brackets. recommended format for cd-rom and dvd periodicals Author 1; Author 2; Author 3; etc. Title of Article. Journal Abbreviation [CDROM or DVD] Year, Volume, pagination or other identifying information. Fleming, S. A.; Jensen, A. W. Substituent Effects on the Photocleavage of Benzyl– Sulfur Bonds. Observation of the “Meta” Effect. J. Org. Chem. [CD-ROM] 1996, 61, 7044. recommended formats for cd-rom and dvd books Author 1; Author 2; etc. Chapter Title. In Book Title, Edition Number [CD-ROM or DVD]; Editor 1, Editor 2, etc., Eds.; Publisher: Place of Publication, Year; Volume Number. Author 1; Author 2; etc. Chapter Title. Book Title, Edition Number [CD-ROM or DVD]; Publisher: Place of Publication, Year; Volume Number. Vining, W. J.; Kotz, J.; Harman, P.; Vining, W.; McDonald, A.; Ward, J. General Chemistry, 3rd ed. [CD-ROM]; Thomson Brooks/Cole: Florence, KY, 2002. Rowley, D.; Ramaker, D. Standard Deviants Chemistry DVD Pack [DVD]; Goldhil Educational: Camarillo, CA, 2000. Chapter 14: References ➤ 323 Many books in CD-ROM or DVD format are reference works, so they have no authors, editors, or chapter titles. The Merck Index, 13.4 [CD-ROM]; Wiley: New York, 2005. Green Chemistry: Meeting Global Challenges [DVD]; American Chemical Society: Washington, DC, 2003. recommended format for conference proceedings on cd-rom or dvd Author 1; Author 2; etc. Title of Presentation. In Title of Conference, Location of Meeting, Date of Meeting [CD-ROM or DVD]; Publisher: Place of Publication, Year; other identifying information. Vasaru, G. Sources of Tritium. In Proceedings of the 2nd International Conference on Nuclear Science and Technology in Iran, Shiraz, Iran, April 27–30, 2004 [CD-ROM]; Conference Permanent Committee, Ed.; Shiraz University: Shiraz, Iran, 2004. Computer Programs References to computer programs must be treated on a case-by-case basis. Five common presentations of computer programs are possible: 1. 2. 3. 4. 5. book format, with the name of the program as the title technical report format CASSI format free style, as a simple listing of program title and author of program thesis style Book Format recommended format Author 1; Author 2; etc. Program Title, version or edition; Publisher: Place of Publication, Year. The recommended format is the same as that for a book citation, except that there are no chapters or pages. The name of the computer program, with any descriptors, is considered the title and is set in italic type. If you wish to include additional information about a program that is important for the reader to know, you may add it at the end of the reference with or without parentheses or append it to the title in parentheses before the semicolon. Binkley, J. S. GAUSSIAN82; Department of Chemistry, Carnegie Mellon University: Pittsburgh, PA, 1982. Main, P. MULTAN 80: A System of Computer Programs for the Automated Solution of Crystal Structures from X-ray Diffraction Data; Universities of York and Louvain: York, England, and Louvain, Belgium, 1980. 324 ➤ The ACS Style Guide recommended format for commercial software and databases Program Title, version or edition; comments; Publisher: Place of Publication, Year. References to data should include the data entry number or other identifying information at the end of the citation. The date of access can also be included if the database is updated frequently. If the data retrieved are calculated data, also cite the software used for the calculation (for example, ACD/Labs). Mathematica, version 5.1; software for technical computation; Wolfram Research: Champaign, IL 2004. MDL CrossFire Commander, version 7; Elsevier MDL: San Leandro, CA, 2004; BRN 635994. Sciﬁnder Scholar, version 2004.2; Chemical Abstracts Service: Columbus, OH, 2004; RN 107-21-1 (accessed Dec 20, 2005); calculated using ACD/Labs software, version 8.14; ACD/Labs 1994–2006. Technical Report Format recommended format Author. Title of Report; Technical Report Number; Publisher: Place of Publication, Year; Pagination (if any). In a citation to a computer program as a technical report, a report or technical report number is included. As with book format, the name of the computer program is considered the title of the technical report. Beurskens, P. T.; Bossman, W. P.; Doesburg, H. M.; Gould, R. O.; van der Hark, Th. E. M.; Prick, P. A. J. DIRDIF: Direct Methods for Difference Structures; Technical Report 1980/1; Crystallographic Laboratory: Toernooiveld, Netherlands, 1980. Johnson, C. K. ORTEP-II: A Fortran Thermal Ellipsoid Plot Program for Crystal Structure Illustrations; Report ORNL-5138; National Technical Information Service, U.S. Department of Commerce: Springﬁeld, VA, 1976. CASSI Format Because of the broad base from which Chemical Abstracts indexes work, computer programs, in the form of technical reports, may be referenced. In such cases, CASSI format would be appropriate. Johnson, C. K. Oak Ridge Natl. Lab., [Rep.] ORNL (U.S.) 1978, ORNL-5348. Free Style When only minimal information (e.g., author and program name) is available, present the information as simply as possible. Chapter 14: References ➤ 325 Programs used in this study included local modiﬁcations of Jacobson’s ALLS, Zalkins’s FORDAP, Busing and Levy’s ORFEE, and Johnson’s ORTEP2. Lozos, G.; Hoffman, B.; Franz, C. SIMI4A, Chemistry Department, Northwestern University. Thesis Style Sheldrick, G. M. SHELX-76: Program for Crystal Structure Determination. Cambridge University, 1976. Collating References Collate all references at the end of the manuscript in numerical order if cited by number and in alphabetical order if cited by author. Do not include items in the reference list that are not cited in the manuscript. Check the publication for which you are writing. Some publications do not allow multiple references to be listed as one numbered entry; they prefer that each numbered entry include only one unique reference. To collate references according to the author–date style, use the following format. 1. Alphabetize in order of the ﬁrst authors’ surnames. 2. When the same ﬁrst author is common to multiple references, • Group the single-author references ﬁrst. List them chronologically. To distinguish among references having the same year, add a lowercase letter (a, b, c, etc.) to the year. • Group the two-author references next. List them chronologically. To distinguish among references having the same year, add a lowercase letter (a, b, c, etc.) to the year. • Group all multiple-author (three or more) references last. List them chronologically. To distinguish among references having the same year, add a lowercase letter (a, b, c, etc.) to the year. Hamilton, F. J. Biochemistry 2003, 42, 78–86. Hamilton, F. J. J. Agric. Food Chem. 2004a, 52, 1622–1633. Hamilton, F. J. J. Org. Chem. 2004b, 69, 298–306. Hamilton, F. J.; Salvo, P. A. J. Agric. Food Chem. 2005, 53, 918–924. Hurd, R. J. Magn. Reson. 1999, 87, 422. Mills, M. S.; Thurman, E. M. Anal. Chem. 2001, 73, 1985–1990. O’Connor, D. J. Environ. Eng. ASCE 2002, 114, 507–522. Rahwan, R. G., Witiak, D. T., Eds. Calcium Regulation by Calcium Antagonists; ACS Symposium Series 201; American Chemical Society: Washington, DC, 2004. Scarponi, T. M.; Moreno, S. P. Biochemistry 2002, 41, 345–360. 326 ➤ The ACS Style Guide Scarponi, T. M.; Adams, J. S. J. Pharm. Sci. 2003, 92, 703–712. Serpone, N.; Pellizetti, E. Photocatalysis: Fundamentals and Applications; Wiley & Sons: New York, 2004. Tewey, L. P.; Rodriguez, R. E.; Jennes, A. C. J. Agric. Food Chem. 2001, 49, 1879– 1886. Tewey, L. P.; Rodriguez, R. E.; Fortunato, B. D.; Jennes, A. C. Ind. Eng. Chem. Res. 2002a, 41, 465–472. Tewey, L. P.; Hiroshi, C. Y.; Allen, P. R.; Lowe, D. L. Biochemistry 2002b, 41, 11689– 11699. Tewey, L. P.; Rolland, H. J.; Harwood, C. C. J. Org. Chem. 2002c, 67, 3548– 3556. Tewey, L. P.; Allen, P. R.; Levy, M. S. J. Am. Chem. Soc. 2003, 125, 2520. Do not use the Latin terms ibid. (in the same place) or idem (the same) because the actual reference source cannot be searched on electronic databases. Reference/Citation Managers Software programs are available to assist with the process of collecting and collating references. With such programs, researchers can create personal electronic collections or libraries of references and tailor the formatting to any number of uses and publishing guidelines. Citations are parsed into searchable databases of component ﬁelds, and formatting templates draw on the data to produce reference lists in a variety of reference styles. The process is further enhanced by ﬁlters designed to correctly interpret the variety of incoming reference formats. Filters, ﬁelds, and templates are customizable to accommodate additional sources and styles. Additional features have been developed to improve the convenience of these tools, including connection scripts for hundreds of public-access and subscription-based bibliographic databases and increased variety of ﬁeld types to accommodate ﬁgures, cross-linking, personal annotation, etc. Plug-ins are available for word-processing packages to format citations within the text, reference lists, and lists of ﬁgures as authors write. There are also networking options for cooperative reference building and linking to full-text versions of references. Researchers can search literature databases either directly or through a reference manager interface; import text, images, and ﬁgures from journal articles, Web sites, and other reference managers; arrange reference lists in numerous collections or libraries; search and retrieve records by any ﬁeld; format footnotes, endnotes, and stand-alone bibliographies; share and co-edit these lists with colleagues; and export citations in hundreds of publication-speciﬁc styles in several languages. These software packages assist the research process from initial literature searching to writing and editing ﬁnal publications. Leading reference management programs include EndNote, Reference Manager, ProCite, RefWorks, and Biblioscape. EndNote, Reference Manager, and Chapter 14: References ➤ 327 ProCite are currently all owned by Thomson Scientiﬁc and are available as standalone software packages for both Windows and Macintosh platforms. RefWorks is a Web-based program with individual accounts that can be accessed across platforms from any point of Internet access. Biblioscape is available in a variety of stand-alone and Web-based options. For the most part, these programs cover the gamut of research disciplines and are fairly well populated with ﬁlters and templates speciﬁc to the chemistry literature. Reviews of these and other bibliographic management software tools are regularly available in the library literature. The Thomson Scientiﬁc products were developed independently and still retain distinctive characteristics in their functionality. EndNote focuses on the reference input and output needs of the individual researcher, with hundreds of connection scripts and ﬁlters and more than 1000 citation style templates. EndNote is updated regularly and has a growing number of enhanced features available. Reference Manager has traditionally targeted collaborative reference sharing between colleagues, with networking options that allow multiple users to work on the same reference list for a project. Some of these features are now becoming available in EndNote as well. Reference Manager is only available for the Windows platform. ProCite has focused on managing reference collections with larger numbers of ﬁelds and reference types and more advanced grouping and searching techniques. ProCite has not been updated since version 5 in 2001. RefWorks is published by RefWorks.com and emphasizes the convenience and collaborative nature of Web-based software. The program and updates are provided on the RefWorks server, and users’ bibliographic data are stored there as well. Multiuser accounts are available for collaborative work. The options for ﬁlters, ﬁelds, reference types, and templates are less developed in RefWorks than in the other tools discussed here and do not include ﬁlters or templates for ACS journal styles. Biblioscape is published by CG Information, founded by scientists speciﬁcally to manage scientiﬁc and electronic information. Biblioscape is a suite of products with different sets of features designed for a variety of users, including undergraduate and graduate students, researchers, and librarians. Options include Web access, intranet, and freeware editions. More than 1000 output styles are available, including the ACS journal styles. ➤➤➤➤➤ APPENDIX 14-1 CASSI Abbreviations for the 1000+ Most Commonly Cited Journals This appendix lists the Chemical Abstracts Service Source Index, or CASSI, abbreviations for more than 1000 of the most commonly cited journals. Note that some journals of the same name are published in more than one city. Authors should check the journal name carefully and include the city to prevent misunderstanding. ACS Symp. Ser. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. Acta Crystallogr., Sect. D: Biol. Crystallogr. Acta Crystallogr., Sect. E: Struct. Rep. Online Acta Hortic. Acta Mater. Acta Pharmacol. Sin. Acta Phys. Pol., B Adv. Exp. Med. Biol. Adv. Mass Spectrom. Adv. Mater. (Weinheim, Ger.) Adv. Sci. Technol. (Faenza, Italy) Adv. Space Res. Adv. Synth. Catal. AIChE J. AIDS (London, U.K.) AIDS Res. Hum. Retroviruses AIP Conf. Proc. Alcohol.: Clin. Exp. Res. Aliment. Pharmacol. Ther. Am. Heart J. Am. J. Cardiol. Am. J. Clin. Nutr. Am. J. Hum. Genet. Am. J. Obstet. Gynecol. Am. J. Pathol. Am. J. Physiol. Am. J. Respir. Cell Mol. Biol. Am. J. Vet. Res. Am. Mineral. Anal. Bioanal. Chem. Anal. Biochem. Anal. Chem. Anal. Chim. Acta Anal. Lett. Anal. Sci. Analyst (Cambridge, U.K.) Anesth. Analg. (Hagerstown, MD, U.S.) Anesthesiology Angew. Chem., Int. Ed. Anim. Genet. Ann. N.Y. Acad. Sci. Ann. Neurol. Annu. Rep.—Conf. Electr. Insul. Dielectr. Phenom. Annu. Tech. Conf.—Soc. Plast. Eng. Anti-Cancer Drugs Anticancer Res. Antimicrob. Agents Chemother. Antioxid. Redox Signaling Reprinted from CASSI Annual Collective Issue for January–December 2004; American Chemical Society: Washington, DC, 2004; pp 42I–45I. Copyright 2004 American Chemical Society. 328 Chapter 14: References Appl. Biochem. Biotechnol. Appl. Catal., A Appl. Catal., B Appl. Environ. Microbiol. Appl. Geochem. Appl. Microbiol. Biotechnol. Appl. Opt. Appl. Organomet. Chem. Appl. Phys. A: Mater. Sci. Process. Appl. Phys. B: Lasers Opt. Appl. Phys. Lett. Appl. Radiat. Isot. Appl. Spectrosc. Appl. Surf. Sci. Aquaculture Aquat. Toxicol. Arch. Biochem. Biophys. Arch. Environ. Contam. Toxicol. Arch. Pharmacal Res. Arch. Virol. ARKIVOC (Gainesville, FL, U.S.) Arterioscler., Thromb., Vasc. Biol. Arthritis Rheum. Asian–Australas. J. Anim. Sci. Asian J. Chem. Astron. Astrophys. Astron. J. Astron. Soc. Pac. Conf. Ser. Astrophys. J. Astrophys. J., Suppl. Ser. Atherosclerosis (Amsterdam, Neth.) Atmos. Chem. Phys. Atmos. Environ. Aust. J. Chem. Azerb. Khim. Zh. Bandaoti Xuebao Behav. Brain Res. Biochem. Biophys. Res. Commun. Biochem. Eng. J. Biochem. J. Biochem. Pharmacol. Biochem. Soc. Trans. Biochem. Syst. Ecol. Biochemistry Biochemistry (Moscow, Russ. Fed.) Biochim. Biophys. Acta ➤ Bioconjugate Chem. Bioinformatics Biol. Chem. Biol. Pharm. Bull. Biol. Psychiatry Biol. Reprod. Biol. Trace Elem. Res. Biomacromolecules Biomaterials Bioorg. Med. Chem. Bioorg. Med. Chem. Lett. Biophys. Chem. Biophys. J. Biopolymers Bioresour. Technol. Biosci., Biotechnol., Biochem. Biosens. Bioelectron. BioTechniques Biotechnol. Bioeng. Biotechnol. Lett. Biotechnol. Prog. Blood BMC Bioinf. Bone (San Diego, CA, U.S.) Bone Marrow Transplant. Br. J. Anaesth. Br. J. Cancer Br. J. Clin. Pharmacol. Br. J. Haematol. Br. J. Nutr. Br. J. Pharmacol. Brain Res. Breast Cancer Res. Treat. Bul. Stiint. Univ. “Politeh.” Timisoara Rom., Ser. Chim. Ing. Mediului Bull. Chem. Soc. Jpn. Bull. Environ. Contam. Toxicol. Bull. Exp. Biol. Med. Bull. Korean Chem. Soc. Bunseki Kagaku C. R. Chim. Cailiao Kexue Yu Gongcheng Xuebao Can. J. Chem. Cancer (New York, NY, U.S.) Cancer Biol. Ther. Cancer Cell 329 330 ➤ The ACS Style Guide Cancer Chemother. Pharmacol. Cancer Epidemiol., Biomarkers Prev. Cancer Genet. Cytogenet. Cancer Lett. (Amsterdam, Neth.) Cancer Res. Cancer Sci. Carbon Carbohydr. Polym. Carbohydr. Res. Carcinogenesis Cardiovasc. Res. Catal. Commun. Catal. Lett. Catal. Today Cell (Cambridge, MA, U.S.) Cell Biol. Int. Cell Cycle Cell Death Differ. Cell. Mol. Life Sci. Cell. Signalling Cem. Concr. Compos. Cem. Concr. Res. Ceram. Eng. Sci. Proc. Ceram. Int. Ceram. Trans. Cereal Chem. Chem. Biol. Chem. Commun. (Cambridge, U.K.) Chem. Eng. J. (Amsterdam, Neth.) Chem. Eng. News Chem. Eng. Process. Chem. Eng. Res. Des. Chem. Eng. Sci. Chem.—Eur. J. Chem. Geol. Chem. Heterocycl. Compd. (New York, NY, U.S.) Chem. Ing. Tech. Chem. Lett. Chem. Mater. Chem. Nat. Compd. Chem. Pet. Eng. Chem. Pharm. Bull. Chem. Phys. Chem. Phys. Lett. Chem. Res. Chin. Univ. Chem. Res. Toxicol. Chem. Rev. (Washington, DC, U.S.) Chem. Sens. ChemBioChem Chemosphere ChemPhysChem Chest Chin. Chem. Lett. Chin. J. Chem. Chin. Med. J. (Beijing, China, Engl. Ed.) Chin. Sci. Bull. Chromatographia Circ. Res. Circulation Clin. Biochem. Clin. Cancer Res. Clin. Chem. (Washington, DC, U.S.) Clin. Chem. Lab. Med. Clin. Chim. Acta Clin. Diagn. Lab. Immunol. Clin. Endocrinol. (Oxford, U.K.) Clin. Exp. Allergy Clin. Exp. Immunol. Clin. Exp. Pharmacol. Physiol. Clin. Immunol. (San Diego, CA, U.S.) Clin. Infect. Dis. Clin. Sci. Collect. Czech. Chem. Commun. Colloid Polym. Sci. Colloids Surf., A Colloids Surf., B Combust. Flame Commun. Soil Sci. Plant Anal. Comp. Biochem. Physiol., Part A: Mol. Integr. Physiol. Comp. Biochem. Physiol., Part B: Biochem. Mol. Biol. Compos. Sci. Technol. Comput. Chem. Eng. Congr. Anu.—Assoc. Bras. Metal. Mater. Corros. Sci. Crit. Care Med. Cryst. Growth Des. Cuihua Xuebao Curr. Biol. Curr. Med. Chem. Chapter 14: References Curr. Microbiol. Curr. Pharm. Des. Curr. Sci. Cytogenet. Genome Res. Cytokine+ Czech. J. Phys. Dalton Trans. Desalination Dev. Biol. (San Diego, CA, U.S.) Dev. Brain Res. Dev. Cell Dev. Dyn. Development (Cambridge, U.K.) Di-San Junyi Daxue Xuebao Diabetes Diabetologia Diamond Relat. Mater. Dianchi Dianyuan Jishu Dier Junyi Daxue Xuebao Diffus. Defect Data, Pt. B Dig. Dis. Sci. Disi Junyi Daxue Xuebao Diyi Junyi Daxue Xuebao DNA Repair Dokl. Biol. Sci. Dokl. Bulg. Akad. Nauk. Dokl. Earth Sci. Dopov. Nats. Akad. Nauk Ukr. Drug Metab. Dispos. Dyes Pigm. EAAP Publ. Earth Planet. Sci. Lett. Ecotoxicol. Environ. Saf. Electroanalysis Electrochem. Commun. Electrochem. Solid-State Lett. Electrochemistry (Tokyo, Jpn.) Electrochim. Acta Electron. Lett. Electrophoresis EMBO J. EMBO Rep. Endocrinology Energy Fuels Environ. Health Perspect. ➤ Environ. Pollut. (Oxford, U.K.) Environ. Sci. Technol. Environ. Technol. Environ. Toxicol. Chem. Enzyme Microb. Technol. Eukaryotic Cell Eur. Food Res. Technol. Eur. J. Biochem. Eur. J. Cancer Eur. J. Clin. Nutr. Eur. J. Endocrinol. Eur. J. Hum. Genet. Eur. J. Immunol. Eur. J. Inorg. Chem. Eur. J. Org. Chem. Eur. J. Pharm. Biopharm. Eur. J. Pharm. Sci. Eur. J. Pharmacol. Eur. Phys. J. A Eur. Phys. J. B Eur. Phys. J. C Eur. Phys. J. D Eur. Polym. J. Eur. Space Agency, [Spec. Publ.] SP Europhys. Lett. Exp. Biol. Med. (Maywood, NJ, U.S.) Exp. Cell Res. Exp. Eye Res. Exp. Gerontol. Exp. Hematol. (New York, NY, U.S.) Exp. Neurol. Expert Opin. Invest. Drugs Expert Opin. Pharmacother. Farmaco FASEB J. FEBS Lett. Fed. Regist. FEMS Immunol. Med. Microbiol. FEMS Microbiol. Lett. Fenxi Huaxue Fenxi Kexue Xuebao Fenxi Shiyanshi Ferroelectrics Fish Physiol. Biochem. Fiz. Khim. Tverd. Tila Fluid Phase Equilib. 331 332 ➤ The ACS Style Guide Food Addit. Contam. Food Chem. Food Chem. Toxicol. Food Hydrocolloids Forensic Sci. Int. Free Radical Biol. Med. Free Radical Res. Fresenius Environ. Bull. Front. Biosci. Front. Sci. Ser. Fuel Fuel Process. Technol. Fusion Energy Fusion Eng. Des. Gangtie Gaodeng Xuexiao Huaxue Xuebao Gaofenzi Cailiao Kexue Yu Gongcheng Gaofenzi Xuebao Gaoneng Wuli Yu Hewuli Gaoxiao Huaxue Gongcheng Xuebao Gastroenterology Gen. Comp. Endocrinol. Gendai Iryo Gene Gene Expression Patterns Gene Ther. Genes Dev. Genetics Genome Res. Genomics Geochim. Cosmochim. Acta Geophys. Res. Lett. Gongcheng Suliao Yingyong Gongneng Cailiao Gongye Cuihua Green Chem. Guangpu Shiyanshi Guangpuxue Yu Guangpu Fenxi Guangzi Xuebao Guisuanyan Xuebao Gut Gynecol. Oncol. Haematologica Handb. Exp. Pharmacol. Han’guk Hwankyong Uisaeng Hakhoechi Han’guk Sikp’um Yongyang Kwahak Hoechi Hecheng Huaxue (1000) Hecheng Xiangjiao Gongye Helv. Chim. Acta Hepatology (Philadelphia, PA, U.S.) Heterocycles Horm. Metab. Res. Huagong Shikan Huagong Xuebao (Chin. Ed.) Huanjing Kexue Xuebao Huanjing Wuran Zhili Jishu Yu Shebei Huaxue Tongbao Huaxue Xuebao Huaxue Yanjiu Yu Yingyong Hum. Mol. Genet. Hum. Mutat. Hum. Pathol. Hum. Reprod. Hydrobiologia Hyomen Gijutsu Hyperﬁne Interact. Hypertension IEEE Electron Device Lett. IEEE J. Quantum Electron. IEEE Trans. Electron Devices IEEE Trans. Magn. IEEE Trans. Nucl. Sci. Igaku no Ayumi Immunol. Lett. Immunology Ind. Eng. Chem. Res. Indian J. Chem., Sect. A: Inorg., Bioinorg., Phys., Theor. Anal. Chem. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. Indian J. Environ. Prot. Indian J. Pharm. Sci. Infect. Immun. Inﬂammation Res. Inorg. Chem. Inorg. Chem. Commun. Inorg. Chim. Acta Inorg. Mater. Insect Biochem. Mol. Biol. Inst. Phys. Conf. Ser. Int. Conf. Thermoelectr. Int. Congr. Ser. Int. DATA Ser., Sel. Data Mixtures, Ser. A Chapter 14: References Int. Immunol. Int. Immunopharmacol. Int. J. Antimicrob. Agents Int. J. Biochem. Cell Biol. Int. J. Cancer Int. J. Food Microbiol. Int. J. Heat Mass Transfer Int. J. Hydrogen Energy Int. J. Mass Spectrom. Int. J. Mod. Phys. B Int. J. Mol. Med. Int. J. Nanosci. Int. J. Oncol. Int. J. Parasitol. Int. J. Pharm. Int. J. Quantum Chem. Int. J. Syst. Evol. Microbiol. Integr. Ferroelectr. Intermetallics IP.com J. ISIJ Int. Izv. Akad. Nauk, Ser. Fiz. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. J. Agric. Food Chem. J. Allergy Clin. Immunol. J. Alloys Compd. J. Am. Ceram. Soc. J. Am. Chem. Soc. J. Am. Coll. Cardiol. J. Am. Oil Chem. Soc. J. Am. Soc. Mass Spectrom. J. Am. Soc. Nephrol. J. Anal. Appl. Pyrolysis J. Anal. At. Spectrom. J. Anal. Chem. J. Anim. Sci. (Savoy, IL, U.S.) J. Antimicrob. Chemother. J. AOAC Int. J. Appl. Crystallogr. J. Appl. Electrochem. J. Appl. Microbiol. J. Appl. Phys. J. Appl. Physiol. J. Appl. Polym. Sci. J. Appl. Spectrosc. ➤ 333 J. Bacteriol. J. Biochem. (Tokyo, Jpn.) J. Biol. Chem. J. Biomed. Mater. Res., Part A J. Biomed. Mater. Res., Part B J. Biomol. NMR J. Biosci. Bioeng. J. Biotechnol. J. Bone Miner. Res. J. Cardiovasc. Pharmacol. J. Catal. J. Cell. Biochem. J. Cell Biol. J. Cell. Physiol. J. Cell Sci. J. Ceram. Soc. Jpn. J. Chem. Ecol. J. Chem. Educ. J. Chem. Eng. Data J. Chem. Eng. Jpn. J. Chem. Inf. Comput. Sci. J. Chem. Phys. J. Chem. Res., Synop. J. Chem. Technol. Biotechnol. J. Chin. Chem. Soc. (Taipei, Taiwan) J. Chromatogr., A J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. J. Clin. Endocrinol. Metab. J. Clin. Invest. J. Clin. Microbiol. J. Colloid Interface Sci. J. Comp. Neurol. J. Comput. Chem. J. Comput. Electron. J. Controlled Release J. Coord. Chem. J. Cryst. Growth J. Dairy Sci. J. Electroanal. Chem. J. Electrochem. Soc. J. Electron. Mater. J. Endocrinol. J. Environ. Eng. (Reston, VA, U.S.) J. Environ. Monit. J. Environ. Qual. 334 ➤ The ACS Style Guide J. Environ. Radioact. J. Environ. Sci. Health, Part A: Toxic/ Hazard. Subst. Environ. Eng. J. Essent. Oil Res. J. Eur. Ceram. Soc. J. Exp. Biol. J. Exp. Bot. J. Exp. Med. J. Exp. Theor. Phys. J. Fluorine Chem. J. Food Prot. J. Food Sci. J. Gen. Virol. J. Geophys. Res., [Atmos.] J. Hazard. Mater. J. Hepatol. J. Heterocycl. Chem. J. Histochem. Cytochem. J. Hypertens. J. Immunol. J. Immunol. Methods J. Inclusion Phenom. Macrocyclic Chem. J. Indian Chem. Soc. J. Infect. Dis. J. Inorg. Biochem. J. Invest. Dermatol. J. Korean Ceram. Soc. J. Korean Phys. Soc. J. Leukocyte Biol. J. Lipid Res. J. Liq. Chromatogr. Relat. Technol. J. Low Temp. Phys. J. Lumin. J. Magn. Magn. Mater. J. Magn. Reson. J. Mass Spectrom. J. Mater. Chem. J. Mater. Process. Technol. J. Mater. Res. J. Mater. Sci. J. Mater. Sci. Lett. J. Mater. Sci.: Mater. Electron. J. Mater. Sci.: Mater. Med. J. Mater. Sci. Technol. (Shenyang, China) J. Med. Chem. J. Med. Genet. J. Med. Virol. J. Membr. Sci. J. Metastable Nanocryst. Mater. J. Microbiol. Biotechnol. J. Microbiol. Methods J. Mol. Biol. J. Mol. Catal. A: Chem. J. Mol. Catal. B: Enzym. J. Mol. Cell. Cardiol. J. Mol. Evol. J. Mol. Liq. J. Mol. Spectrosc. J. Mol. Struct. J. Nat. Prod. J. Natl. Cancer Inst. J. Neurochem. J. Neuroimmunol. J. Neurophysiol. J. Neurosci. J. Neurosci. Res. J. Non-Cryst. Solids J. Nucl. Mater. J. Nutr. J. Opt. Soc. Am. B J. Optoelectron. Adv. Mater. J. Org. Chem. J. Organomet. Chem. J. Pathol. J. Pharm. Biomed. Anal. J. Pharm. Pharmacol. J. Pharm. Sci. J. Pharmacol. Exp. Ther. J. Pharmacol. Sci. (Tokyo, Jpn.) J. Photochem. Photobiol., A J. Phys. A: Math. Gen. J. Phys. B: At., Mol. Opt. Phys. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. Solids J. Phys.: Condens. Matter J. Phys. D: Appl. Phys. J. Phys. G: Nucl. Part. Phys. J. Phys. IV J. Phys. Org. Chem. J. Phys. Soc. Jpn. J. Physiol. (Oxford, U.K.) Chapter 14: References J. Plant Physiol. J. Polym. Sci., Part A: Polym. Chem. J. Polym. Sci., Part B: Polym. Phys. J. Power Sources J. Quant. Spectrosc. Radiat. Transfer J. Radioanal. Nucl. Chem. J. Raman Spectrosc. J. Rheumatol. J. Sci. Food Agric. J. Sep. Sci. J. Solid State Chem. J. Steroid Biochem. Mol. Biol. J. Surg. Res. J. Therm. Anal. Calorim. J. Thromb. Haemostasis J. Univ. Chem. Technol. Metall. J. Urol. (Hagerstown, MD, U.S.) J. Vac. Sci. Technol., A J. Vac. Sci. Technol., B: Microelectron. Nanometer Struct.—Process., Meas., Phenom. J. Vet. Pharmacol. Ther. J. Virol. J. Virol. Methods JAERI—Conf JETP Lett. Jiegou Huaxue Jikken Igaku Jingxi Huagong Jingxi Huagong Zhongjianti Jinshu Xuebao Jisuanji Yu Yingyong Huaxue Jixie Gongcheng Cailiao Jpn. J. Appl. Phys., Part 1 Jpn. J. Appl. Phys., Part 2 Kagaku to Kogyo (Tokyo, Jpn.) Kagaku to Kyoiku Kagaku to Seibutsu KEK Proc. Key Eng. Mater. Kidney Int. Kogyo Zairyo Kongop Hwahak Korean J. Chem. Eng. Lab. Invest. Lancet ➤ 335 Langmuir Lect. Notes Phys. Leuk. Lymphoma Leuk. Res. Leukemia Life Sci. Liq. Cryst. Low Temp. Phys. Lung Biol. Health Dis. Macromol. Chem. Phys. Macromol. Rapid Commun. Macromol. Symp. Macromolecules Magn. Reson. Chem. Mar. Pollut. Bull. Mater. Chem. Phys. Mater. Lett. Mater. Res. Bull. Mater. Res. Soc. Symp. Proc. Mater. Sci. Eng., A Mater. Sci. Eng., B Mater. Sci. Eng., C Mater. Sci. Forum Mater. Sci. Technol. Mater. Trans. Meas. Sci. Technol. Meat Sci. Mech. Dev. Med. Hypotheses Meded.—Fac. Landbouwkd. Toegepaste Biol. Wet. (Univ. Gent) Metab., Clin. Exp. Metall. Mater. Trans. A Meteorit. Planet. Sci. Methods Enzymol. Methods Mol. Biol. (Totowa, NJ, U.S.) Methods Mol. Med. Microbes Infect. Microbiology (Reading, U.K.) Microchim. Acta Microelectron. Eng. Microelectron. Reliab. Microporous Mesoporous Mater. Miner. Eng. Mod. Phys. Lett. A Mol. Biochem. Parasitol. 336 ➤ The ACS Style Guide Mol. Biol. Cell Mol. Biol. Evol. Mol. Brain Res. Mol. Cancer Ther. Mol. Cell Mol. Cell. Biochem. Mol. Cell. Biol. Mol. Cell. Endocrinol. Mol. Cell. Neurosci. Mol. Cryst. Liq. Cryst. Mol. Ecol. Mol. Ecol. Notes Mol. Endocrinol. Mol. Genet. Genomics Mol. Genet. Metab. Mol. Immunol. Mol. Med. (Tokyo, Jpn.) Mol. Microbiol. Mol. Pharmacol. Mol. Phylogenet. Evol. Mol. Phys. Mol. Plant–Microbe Interact. Mol. Psychiatry Mol. Reprod. Dev. Mol. Ther. Mon. Not. R. Astron. Soc. Monatsh. Chem. Mutat. Res. N. Engl. J. Med. Nano Lett. Nanotechnology NASA Conf. Publ. Nat. Biotechnol. Nat. Cell Biol. Nat. Genet. Nat. Immunol. Nat. Mater. Nat. Med. (New York, NY, U.S.) NATO Sci. Ser., II NATO Sci. Ser., IV NATO Sci. Ser., Ser. I Nature (London, U.K.) Naunyn-Schmiedeberg’s Arch. Pharmacol. Nephrol., Dial., Transplant. Neuron Neurobiol. Aging Neurobiol. Dis. Neurochem. Int. Neurochem. Res. Neurology Neuropharmacology Neuropsychopharmacology NeuroReport Neurosci. Lett. Neuroscience (Oxford, U.K.) New J. Chem. New Phytol. Nippon Kessho Seicho Gakkaishi Nippon Kikai Gakkai Ronbunshu, B-hen Nongyao Nongye Huanjing Kexue Xuebao Nucl. Eng. Des. Nucl. Fusion Nucl. Instrum. Methods Phys. Res., Sect. A Nucl. Instrum. Methods Phys. Res., Sect. B Nucl. Phys. A Nucl. Phys. B Nucl. Phys. B, Proc. Suppl. Nucleic Acids Res. Nucleosides, Nucleotides Nucleic Acids Oncogene Oncol. Rep. Opt. Commun. Opt. Lett. Opt. Mater. (Amsterdam, Neth.) Opt. Spectrosc. Org. Biomol. Chem. Org. Lett. Org. Process Res. Dev. Organohalogen Compd. Organometallics Orient. J. Chem. Oxford Monogr. Med. Genet. Pain Pediatr. Res. Peptides (New York, NY, U.S.) Pﬂuegers Arch. Pharm. Chem. J. Pharm. Res. Pharmacol., Biochem. Behav. Pharmacol. Res. Pharmazie Chapter 14: References Philos. Mag. Phosphorus, Sulfur Silicon Relat. Elem. Photochem. Photobiol. Photochem. Photobiol. Sci. Phys. At. Nucl. Phys. Chem. Chem. Phys. Phys. Fluids Phys. Lett. A Phys. Lett. B Phys. Plasmas Phys. Rev. A: At., Mol., Opt. Phys. Phys. Rev. B: Condens. Matter Mater. Phys. Phys. Rev. C: Nucl. Phys. Phys. Rev. D: Part. Fields Phys. Rev. E: Stat., Nonlinear, Soft Matter Phys. Phys. Rev. Lett. Phys. Solid State Phys. Status Solidi A Phys. Status Solidi B Phys. Status Solidi C Physica B (Amsterdam, Neth.) Physica C (Amsterdam, Neth.) Physica E (Amsterdam, Neth.) Physiol. Behav. Physiol. Genomics Physiol. Plant. Phytochemistry (Elsevier) Planta Plant Cell Plant Cell Physiol. Plant J. Plant Mol. Biol. Plant Physiol. Plant Sci. (Amsterdam, Neth.) Plant Soil Planta Med. Plasma Phys. Controlled Fusion Plast. Massy Pol. J. Chem. Polyhedron Polym. Degrad. Stab. Polym. Eng. Sci. Polym. Int. Polym. J. (Tokyo, Jpn.) Polym. Mater. Sci. Eng. ➤ 337 Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) Polymer Poult. Sci. Poverkhnost Powder Technol. Pramana Prepr.—Am. Chem. Soc., Div. Pet. Chem. Prepr. Ext. Abstr. ACS Natl. Meet., Am. Chem. Soc., Div. Environ. Chem. Prepr. Symp.—Am. Chem. Soc., Div. Fuel Chem. Proc.—Annu. Conf., Am. Water Works Assoc. Proc.—Electrochem. Soc. Proc. Natl. Acad. Sci. U.S.A. Proc. SPIE—Int. Soc. Opt. Eng. Proc.—Water Qual. Technol. Conf. Process Biochem. (Oxford, U.K.) Prog. Org. Coat. Prostaglandins, Leukotrienes Essent. Fatty Acids Prostate (New York, NY, U.S.) Protein Expression Purif. Protein Sci. Proteins: Struct., Funct., Bioinf. Proteomics Psychopharmacology (Berlin, Ger.) Publ. Australas. Inst. Min. Metall. Pure Appl. Chem. Quim. Nova Radiat. Phys. Chem. Radiat. Prot. Dosim. Ranliao Huaxue Xuebao Rapid Commun. Mass Spectrom. React. Kinet. Catal. Lett. Recents Prog. Genie Procedes Regul. Pept. Rengong Jingti Xuebao Reproduction (Bristol, U.K.) Res. Discl. Rev. Chim. (Bucharest, Rom.) Rev. Mex. Astron. Astroﬁs., Ser. Conf. Rev. Roum. Chim. Rev. Sci. Instrum. RILEM Proc. 338 ➤ The ACS Style Guide Rinsho Men’eki RNA Russ. Chem. Bull. Russ. J. Appl. Chem. Russ. J. Coord. Chem. Russ. J. Electrochem. Russ. J. Gen. Chem. Russ. J. Genet. Russ. J. Org. Chem. Saibo Kogaku Sci. Total Environ. Science (Washington, DC, U.S.) Scr. Mater. Sekitan Kagaku Kaigi Happyo Ronbunshu Semicond. Sci. Technol. Semiconductors Sens. Actuators, A Sens. Actuators, B Sep. Purif. Technol. Sep. Sci. Technol. Sepu Shandong Daxue Xuebao, Yixueban Shengwu Yixue Gongchengxue Zazhi Shijie Huaren Xiaohua Zazhi Shipin Kexue (Beijing, China) Shiyou Huagong Shiyou Lianzhi Yu Huagong Shock Soc. Automot. Eng., [Spec. Publ.] SP Soil Biol. Biochem. Soil Sci. Soc. Am. J. Sol. Energy Mater. Sol. Cells Solid State Commun. Solid-State Electron. Solid State Ionics Solid State Sci. Spec. Publ.—R. Soc. Chem. Spectrochim. Acta, Part A Spectrochim. Acta, Part B Steroids Stroke Structure (Cambridge, MA, U.S.) Stud. Surf. Sci. Catal. Supercond. Sci. Technol. Surf. Coat. Technol. Surf. Interface Anal. Surf. Sci. Symp.—Int. Astron. Union Synlett Synth. Commun. Synth. Met. Synthesis Talanta Tanpakushitsu Kakusan Koso Tech. Phys. Tech. Phys. Lett. Tetrahedron Tetrahedron: Asymmetry Tetrahedron Lett. Tetsu to Hagane Text. Res. J. Tezhong Zhuzao Ji Youse Hejin THEOCHEM Theor. Appl. Genet. Theriogenology Thermochim. Acta Thin Solid Films Thromb. Haemostasis Thromb. Res. Tissue Antigens Tissue Eng. Tokyo Daigaku Genshiryoku Kenkyu Sogo Senta Shinpojumu Top. Catal. Toxicol. Appl. Pharmacol. Toxicol. Lett. Toxicol. Sci. Toxicology Toxicon Trans. Am. Foundry Soc. Trans. Nonferrous Met. Soc. China Transition Met. Chem. (Dordrecht, Neth.) Transplant. Proc. Transplantation Trends Opt. Photonics Trends Pharmacol. Sci. Tsvetn. Met. (Moscow, Russ. Fed.) Ukr. Khim. Zh. (Russ. Ed.) Vaccine Vacuum VDI—Ber. Vet. Microbiol. Chapter 14: References Virology Virus Res. Vysokomol. Soedin., Ser. A Ser. B Water, Air, Soil Pollut. Water Res. Water Sci. Technol. Wear World J. Gastroenterol. Wuji Cailiao Xuebao Wuji Huaxue Xuebao Wuli Huaxue Xuebao Wuli Xuebao Xibao Yu Fenzi Mianyixue Zazhi Xiyou Jinshu Xiyou Jinshu Cailiao Yu Gongcheng Yaoxue Xuebao Yingyong Huaxue Yingyong Shengtai Xuebao Youji Huaxue Z. Anorg. Allg. Chem. Z. Kristallogr.—New Cryst. Struct. Z. Metallkd. Z. Naturforsch., B: Chem. Sci. Z. Naturforsch., C: J. Biosci. Zairyo ➤ 339 Zavod. Lab., Diagn. Mater. Zh. Fiz. Khim. Zh. Neorg. Khim. Zhengzhou Daxue Xuebao, Yixueban Zhongcaoyao Zhongguo Bingli Shengli Zazhi Zhongguo Dongmai Yinghua Zazhi Zhongguo Gonggong Weisheng Zhongguo Jiguang Zhongguo Jishui Paishui Zhongguo Shenghua Yaowu Zazhi Zhongguo Shengwu Gongcheng Zazhi Zhongguo Shengwu Huaxue Yu Fenzi Shengwu Xuebao Zhongguo Shouyi Xuebao Zhongguo Suliao Zhongguo Xinyao Zazhi Zhongguo Xitu Xuebao Zhongguo Yaolixue Tongbao Zhongguo Yaoxue Zazhi (Beijing, China) Zhongguo Yiyao Gongye Zazhi Zhongguo Yiyuan Yaoxue Zazhi Zhongguo Youse Jinshu Xuebao Zhonghua Yixue Yichuanxue Zazhi Zhongliu Fangzhi Zazhi ➤➤➤➤➤ APPENDIX 14-2 A Sample CASSI Entry Journal of the American Chemical Society. JACSAT. ISSN 0002–7863 (Absorbed Am. Chem. J.). In English; English sum. History: v1 1879+. w 126 2004. ACS Journals or Maruzen. american chemical society. journal. washington, d. c. Doc. Supplier: CAS. AAP; AB 1905+; ABSR; ARaS; ATVA; AU–M 1893–1918,1920–1926,1928+; AkU 1879–1906,1919+; ArU; ArU–M 1923+; AzTeS; AzU 1889+; C; CL; CLSU; CLSU–M 1895–1897,1905,1908+; CLU–M; CLU–P; CMenSR 1916+; CPT; CSf; CSt; CSt–L; CU; CU–A; CU–I 1920+; CU–M; CU–Riv 1907+; CU–RivA; CU– RivP; CU–S; CU–SB; [etc.] In this example, • Journal of the American Chemical Society is the complete publication title with its abbreviated form indicated by boldface type (J. Am. Chem. Soc.). • JACSAT is the CODEN, a six-character, unique title abbreviation used to represent titles in manual or machine-based information systems. The CODEN source is the International CODEN Directory, administered by Chemical Abstracts Service. The sixth character of each CODEN is a computer-calculated check character that ensures the reliability of the CODEN in computer-based systems. • ISSN 0002–7863 is the International Standard Serial Number (ISSN), assigned by the Library of Congress. • Absorbed Am. Chem. J. is a reference to former titles and to any variant forms of the selected title. • In English; English sum. is the language of the publication, summaries, and tables of contents. • History: v1 1879+ is the history of the publication. Volume 1 began in 1879. The + following the year indicates that the publication is still in existence under that title. • w means weekly. The frequency of publication could also be a for annually, ba for biennially (every two years), bm for bimonthly (every two months), bw for biweekly (every two weeks), d for daily, m for monthly, q for quarterly, sa for semiannually (two times per year), sm for semimonthly (two times per month), or sw for semiweekly (two times per week). 340 Chapter 14: References ➤ 341 • 126 2004 is the volume–year correlation (i.e., the ﬁrst volume number of that year, which is the most recent covered by that edition of CASSI; volume 126 was the ﬁrst volume number of 2004). • ACS Journals or Maruzen is the publisher or source address or abbreviation. • AMERICAN CHEMICAL SOCIETY. JOURNAL. WASHINGTON, D. C. is the AACR entry. This is the abbreviated entry as catalogued according to the Anglo-American Cataloguing Rules (2nd ed.). It is included here because of its predominance in library collection records. • Doc. Supplier: CAS means that articles are available through the CAS Document Delivery Service. • AAP; AB 1905+; ABSR; etc., is the library holdings information. Libraries are identiﬁed by their National Union Catalog symbols, and holdings are shown by inclusive years. ➤➤➤➤➤ CHAPTER 15 Figures Betsy Kulamer T his chapter discusses methods of preparing and submitting the ﬁgures and other illustrations that accompany a scientiﬁc paper for publication. The past 10 years have seen a radical technological shift in the way ﬁgures are created by authors and handled by publishers. Whereas authors previously submitted ﬁgures that were camera-ready—that is, ready for the printer’s camera to photograph before making printing plates— today many authors create ﬁgures using computer software, and most publishers encourage electronic versions of ﬁgures. This chapter presents guidelines for working with ﬁgures using the computer tools currently in widespread use; it also includes recommendations regarding the use of color, fonts, and scanners, as well as good style for citing and captioning ﬁgures. Technical requirements and certain style points differ from publisher to publisher and from journal to journal, so bear in mind that this chapter presents general guidelines. ACS journals have some speciﬁc requirements that may differ from the general guidelines presented here, and these are noted throughout the chapter. As always, before you ﬁnalize ﬁgures for your manuscript, you should consult your publisher’s guidelines for submitting artwork. For ACS journals, consult recent issues as well as the Guide, Notes, or Instructions for Authors that appear in each journal’s ﬁrst issue of the year or at https://paragon.acs.org/ paragon/index.jsp (see “Author Information”). For ACS books, consult the brochure “How To Prepare Your Manuscript for the ACS Symposium Series” or see “Info for Authors” at https://pubs.acs.org/books. Copyright 2006 American Chemical Society 343 344 ➤ The ACS Style Guide ➤➤➤➤➤ Box 15-1. Do I Need a Figure or a Table? Do I want the basic point to be communicated at a glance? Use a ﬁgure. Do I want the reader to see trends and relationships? Use a ﬁgure. Do I want the reader to see exact numbers? Use a table. Do I want to communicate a lot of information with words? Use a table. When To Use Figures A ﬁgure is an illustration used in scientiﬁc or scholarly publishing. Figures can be graphs of data, photographs, sketches, ﬂow charts, and so on. Figures can play a major role in highlighting, clarifying, and summarizing data and results and can substantially increase the readers’ comprehension of the text by communicating visually. For example, line graphs show trends. Bar graphs compare magnitudes. Pie charts show relative portions of a whole. Photographs can provide absolute proof of ﬁndings. In general, ﬁgures should be used when the picture really is worth a thousand (or so) words. However, ﬁgures can decrease a reader’s comprehension, and they can cause outright confusion if they are poorly rendered or cluttered, if they do little more than repeat data already presented in text, or, worse, if they present information at odds with the text. An excessive number of ﬁgures can dilute the value of any individual ﬁgure: when presented with too many ﬁgures, a reader may look carefully at none of them. Figures should not be used to present data that would be better presented in a table. See Box 15-1 and Chapter 16, “Tables.” The cost of publishing ﬁgures has decreased substantially over the past two decades, partly because authors are able to prepare better quality ﬁgures (so the publisher does not have to) and partly because of the shift to electronic methods of Web and print publishing that are less cumbersome than earlier technologies, which required a high-quality, pristine paper original of all art. The cost of publishing color ﬁgures has also decreased substantially because most color photographs can now be provided in electronic form and no longer require expensive color separations before being put on a printing press. The cost of using color in Web publications is inconsequential (although color should still be used carefully to enhance your meaning, not just to grab attention). See Box 15-2. Chapter 15: Figures ➤ 345 ➤➤➤➤➤ Box 15-2. Do I Need To Use Color? Do I need color to make the picture comprehensible to the reader? Color should be used only when it is essential to understand the chemical nature of the material in the picture. Otherwise the picture should be prepared in black and white. Do I need color in my line graph, bar graph, or pie chart? Color is rarely required in these ﬁgures. Lines with varying dash styles in line graphs and distinct grayscale shades in bar graphs or pie charts work as well. Do I need color to catch the reader’s eye? No. Do I need color to organize related information for the reader? No. Judicious use of fonts and careful placement of words and objects usually does just as well. How To Cite Figures All ﬁgures must be “called out”, that is, mentioned or discussed by name and number in the text. (If you cannot ﬁnd a graceful, logical place to put the callout, then you might consider deleting the ﬁgure.) Follow these guidelines in citing ﬁgures. ➤ Capitalize the word “Figure” when it is followed by the ﬁgure number. ➤ Number ﬁgures sequentially with arabic numerals in order of discussion in the text (Figure 1, Figure 2, etc.). ➤ Designate parts of a ﬁgure by using a combination of the arabic numeral and a sequence of consistent labels, usually (but not always) letters: Figure 1a, Figure 1b; Figure 1A, Figure 1B; Figure 1-I, Figure 1-II. Do not cite, for example, Figure 4 and Figure 4A. examples of figure callouts in text The block copolymers may contain a small but detectable fraction of impurities, as shown in Figures 1 and 2. Figures 3–5 show the production of acid-reactive substances in three different oils. The deuterium-labeled substrate gave rise to the partial 1H NMR spectra shown in Figure 2a,b. 346 ➤ The ACS Style Guide As seen in Figure 3b–d, the catalytic wave shows a small but distinct decrease upon addition of the nucleophile. Parts a and b of Figure 4 illustrate that the voltammetric plateau current depends on the number of enzyme monolayers. Curves c–e of Figure 5 were obtained for various methyl groups in the protein. poor examples of figure callouts in text Figure 2c and Figure 2D show… should read Figure 2c,d shows… Figure 3 and Figure 4 show… should read Figures 3 and 4 show… Chemical structures and schemes should not be numbered as figures; they should be labeled according to separate sequences. See Chapter 17, Chemical Structures. How To Prepare Figures At one time, almost all publishers required that ﬁgures be submitted as cameraready artwork. Today, most publishers accept, many encourage, and a few require that ﬁgures be submitted in electronic format. Most scientists store their data on computers and create their ﬁgures using computer software, and good-quality document scanners are in common use. Thus, the submission of electronic ﬁles is simpler than ever before and has the advantage of keeping original data and photographs in the author’s own hands. Satisfactory results in the ﬁnal publication are not guaranteed, however, and the burden rests on authors to prepare ﬁgures to suit the requirements of the medium in which they will be published. Publication Medium The traditional method for publishing books, journals, and other documents is by print publishing, that is, the application of ink on paper. Newer avenues include publishing on the Internet, usually called Web publishing, as well as other formats that are viewed on a computer monitor, such as CD-ROMs. The requirements of ink-on-paper and pixels-on-screen publishing are quite different and may affect your choices regarding ﬁgure creation and ﬁnal electronic format. For printed materials to be satisfactory, the ﬁgure ﬁles must have much detail and therefore must be prepared at a higher resolution, that is, a higher number of pixels per inch (ppi). Paper printers also use a scale called dots per inch or dpi, which you may need to use sometimes. Materials viewed on a computer monitor do not require the same level of detail but—on the Web especially—they must download quickly, so they are prepared at a low resolution. Only for printed materials is color signiﬁcantly more expensive than black-and-white, so in print, color is used conservatively. Conversely, on a computer monitor, color costs nothing additional and is used widely. Chapter 15: Figures ➤ 347 Publishing with ACS: When preparing ﬁgures for ACS journals—which are published in print and on the Web—prepare your ﬁgures to the higher standard required for print. ACS routinely prepares the Web ﬁgures from ﬁles provided for the print ﬁgures. Types of Figure Artwork The two broad categories of ﬁgure artwork are line art and continuous-tone art. Line art consists of black markings on a white background, with no additional colors and no shades of gray (see Figure 15-1A). Line art contains lines, solid shapes, and type (letters or words). Examples of line art include line graphs, ﬂow charts, and scatter plots. (Structures and schemes are usually line art as well; see Chapter 17.) Continuous-tone art (also called halftone art) contains shades of gray (or color) (see Figure 15-1B). Examples of continuous-tone art include photographs (whether black-and-white or color) and drawings or sketches with midtones. In print publishing, line art is straightforwardly rendered by ink on paper. To print continuous-tone art, the shading must be converted into dots through a process called screening. The size and spacing of the dots produces the illusion of shading to the reader’s eye. Halftones do not reproduce type or ﬁne lines well because screening distorts the edges of the letters and lines. On a computer monitor, all text and images are converted to uniformly sized pixels. Until recently, publishers strongly encouraged authors to submit ﬁgures as line art, with halftones reserved for photographs. Currently available software and the prevalence of electronic ﬁle submission is bringing a third category of art into more common use. Grayscale line art is black-and-white art that contains gray shading alongside ﬁne lines and type (see Figure 15-1C). Grayscale line art may be used for pie charts, bar graphs, and area graphs, where different sections are distinguished by different shades of gray. A fourth category of art is a combination of a photograph with some type, or a combo (see Figure 15-1D). An example might be a photomicrograph with a unitof-measure legend in one corner; another might be a photograph with callouts identifying parts of an image, such as a piece of equipment. If there is only a small amount of type (as in the ﬁrst example), then a combo can be handled like other halftones. When there is more type (as in the second example), then a combo requires special handling, because screened type loses legibility very quickly. Publishing with ACS: For ACS journals, line art should be created and saved at 1200 ppi. Grayscale art, including grayscale line art and combos, should be created and saved at 600 ppi. Halftones, whether black-andwhite or color, should be created and saved at 300 ppi. 348 ➤ The ACS Style Guide A B Figure 15-1. Examples of categories of figure art: (A) line art, (B) halftone or continuous-tone art, (C) grayscale line art, and (D) a combo. Sources: (A) Reprinted from Stevens, L. L.; Haycraft, J. J.; Eckhardt, C. J. Cryst. Growth Des. 2005, 5, 2060–2065. Copyright 2005 American Chemical Society. (B) Photograph courtesy of Raj Mehta. Reprinted from Reagent Chemicals, 10th ed. Copyright 2006 American Chemical Society. (C) Reprinted from Watanabe, K.; Niwa, S.; Mori, Y. H. J. Chem. Eng. Data 2005, 50, 1672–1676. Copyright 2005 American Chemical Society. (D) Adapted from Odelius, K.; Plikk, P.; Albertsson, A.-C. Biomacromolecules 2005, 6, 2718–2725. Copyright 2005 American Chemical Society. Chapter 15: Figures C D Figure 15-1. Continued. ➤ 349 350 ➤ The ACS Style Guide Use of Color The use of color in ﬁgures depends partly on the medium and partly on a particular publisher’s preferences. As mentioned earlier, color can be used in Web publishing at virtually no cost, so the only restrictions have to do with scientiﬁc effectiveness and good taste. Color in print publishing adds to the cost, so before preparing ﬁgures in color, you should ascertain a publisher’s policies on color. Publishing with ACS: ACS journals do not require authors to pay the cost of color illustrations. Authors who publish color ﬁgures in ACS books are asked to pay half the cost. In publications, color is produced by one of three modes: • Black-and-white, or B&W: For print publications, where only one color of ink (usually black) is used. • Cyan–magenta–yellow–black, or CMYK (also called four-color): For print publications, where all shades of color are produced by layering screened dots of four standardized inks. • Red–green–blue, or RGB: For Web publications and others viewed on computer monitors, where all shades of color are produced by overlapping red, green, and blue light. Most publishers can switch electronically from CMYK to RGB, although it is always better to use the publisher’s preferred format. Switching from one of the color formats to B&W may produce unsatisfactory results, however. If the gray tones that result are hard to distinguish from each other, a ﬁgure that was intelligible in color can become meaningless in B&W. For this reason, it is always better to prepare art that will be reproduced in black and white as B&W. Electronic File Formats Many software packages are available today for drawing, scanning, and manipulating ﬁgures. When a ﬁgure is saved in a format that can be read or reopened only by the software that produced it, the ﬁle is called an application ﬁle. Examples include ﬁles with names that end with the sufﬁx .cdx, which can be opened only in Cambridgesoft ChemDraw, or ﬁles with names that end in the sufﬁx .psd, which can be opened only in Adobe Photoshop. Application ﬁles often pose problems in both Web and print publishing because the publisher (or reader) might not have the necessary software to open or view the ﬁle. Many publishers will not accept application ﬁles for ﬁgures. There are a handful of ﬁle formats, however, that can be opened in many different software packages. Drawing and scanning programs generally provide the option of saving to one or more of these formats. For example, ChemDraw and Chapter 15: Figures ➤ 351 Photoshop will both export ﬁgures as TIFFs, a format frequently used for print publications. The most universally accepted of these formats are the following: For Print • Encapsulated PostScript, or EPS. PostScript is a programming language developed by Adobe to describe pages, graphics, and fonts; an EPS ﬁle is coded to be embedded in a large PostScript ﬁle. • Tagged Image File Format, or TIFF. TIFFs describe an image by dividing it into a grid of pixels and assigning a value to each square. The quality of a TIFF image depends on its resolution (in ppi), that is, the size of the original grid. For Web • Graphics Interchange Format, or GIF. GIF is a pixel-based format like TIFF, except the resolution is preset at 72 ppi, which is appropriate for the Web but seldom acceptable for print. • Joint Photographic Experts Group, or JPEG. JPEG is another pixel-based format like TIFF but capable of higher resolutions than GIFs. JPEGs, however, are actually compressed ﬁles, and they lose small amounts of digital information every time they are opened, recompressed, and saved, so JPEG images tend to degrade with repeated processing. Only “fresh”, high-quality JPEGs are suitable for print publication. For Print and Web Many publishers now accept properly created Portable Document Files, or PDFs. A PDF document is created when an application ﬁle produced by any of a number of software programs is “distilled”, using software such as Adobe’s Acrobat Distiller. The PDF document can be viewed on any platform using viewing software such as Adobe’s Acrobat Reader, regardless of whether the viewer has the original application software. Publishing with ACS: For ACS journals, ﬁgure art that will be submitted in PDF format should be distilled using Adobe Acrobat Distiller’s “Press Quality” setting. With so many different software packages and ﬁle formats, there is no single “right” way to prepare ﬁgures for publication. A few common paths are listed here: • A line-art ﬁgure is drawn in an application such as Adobe Illustrator, Macromedia Freehand, or Corel Draw and exported as an EPS or a TIFF ﬁle. • A B&W photograph is scanned with the scanner’s software and saved as a grayscale TIFF. 352 ➤ The ACS Style Guide Table 15-1. Image File Formats and Their Suitability by Publication Medium and Type of Figurea Publication Medium Optimal ppib Web GIF 72 H X X R R R R RGB JPEG 72 R X X R R R R B&W JPEG 300 X R X X R R R CMYK JPEG 300 X X R X R R R 600–1200 X X R R X X X 1200 X H X H X X X R File Format B&W Color Printing Printing Best Used To Represent Line Art Photo- Grayscale graphs Line Art Combos For Web For Print Bitmap TIFF Grayscale TIFF 600 X H X X H R CMYK TIFF 300 X X H X H R R EPS N/A X R H Hc X Hc Hc a H indicates highly recommended; R indicates recommended; X indicates not recommended. b The optimal number of pixels per inch (ppi) for art prepared to the size at which it will be published. It is always permissible to supply art with a higher ppi than what is listed here. c EPS files are the best way to submit grayscale line art and combos, but the fonts used must be embedded or converted to outlines. • A color digital photograph cropped in Photoshop is saved as a 72 ppi RGB GIF ﬁle for the Web or a 300 ppi CMYK TIFF ﬁle for print. • Grayscale line art is drawn in an application, such as Illustrator or Freehand, and saved as an EPS ﬁle. Table 15-1 lists image ﬁle formats commonly accepted by publishers and their suitability for different publishing media and types of artwork. Several software packages that are in common use can produce satisfactory GIFs for Web publishing but do not export images in a form that is acceptable for the more rigorous requirements of print. Corel WordPerfect and Microsoft Word, Excel, and PowerPoint cannot save ﬁgures as valid PostScript ﬁles or export directly to TIFFs. Box 15-3 offers suggestions for preparing publishable ﬁgures in that program. Sizing Artwork Always determine the size at which your ﬁgures will be printed and prepare the ﬁnal electronic version to those dimensions. Consult guidelines from the publisher ﬁrst. If there are no guidelines, use the following: • For a Web publication, size your artwork so that it is visually appealing and all parts of the graphic are easily readable on your monitor at 100%. Chapter 15: Figures ➤ 353 ➤➤➤➤➤ Box 15-3. Tips for Submitting Figures Created in Excel Microsoft Excel and PowerPoint are widely used to create graphs and other ﬁgures, but they are unable to export to TIFF or any PostScript ﬁle format. Therefore, if ﬁgures prepared with these software programs are destined for print publication, they must be printed on paper ﬁrst and then scanned. (It may also work to submit the ﬁgure as a PDF.) Moreover, the default settings of these programs will not produce satisfactory ﬁgures. The following tips help you get the best results from Excel. • Do not use color to differentiate areas of the ﬁgure. Use black only for a color, and use gray tones to differentiate areas of the ﬁgure. • Be sure that the weight of all lines is at least 0.5 point. Some lines in Excel default to 0.12 point, which is too thin for scanning. If the ﬁgure will be printed large and then reduced, calculate the width of lines accordingly (see the chart below). • Be sure that the type and symbols also will scale down accordingly. • It is better for tick marks to extend into the ﬁgure, rather than extend outside. • Print the ﬁgure on clean, opaque, white paper, using a fresh ink or toner cartridge. Do not use a dot matrix printer. Set the laser or inkjet printer to a resolution of at least 600 ppi. • Scan the ﬁgure to the correct size, and save it as a 600 ppi bitmap TIFF. If your publisher requests the Excel application ﬁle, be sure that the source data are embedded (not linked) in the ﬁle you send. Line width for a typical ﬁgure created in Excel, printed landscape on 8.5 × 11 in. paper, and destined to be printed at a width of 20 or 27 picas: 20 picas (single-column journal) 27 picas (6 x 9 in. book) Approximate reduction 38% 50% Type size in Excel 14 pt 14 pt 5 pt 7 pt Type size after reduction Line width in Excel Line width after reduction 1.5 pt 1 pt 0.5 pt 0.5 pt 354 ➤ The ACS Style Guide Table 15-2. Column Dimensions Most Common in ACS Publications Column Width Publication picas inches Page Length centimeters picas inches centimeters Books, trim size 6 × 9 in. 27 4½ 11 42 7 17½ 7 × 10 in. 33 5½ 13½ 51 8½ 21½ 56 9 23 60 10 25½ 60 10 25½ 8 × 11 in. single column 20 3¼ double column 42 7 8¼ 17½ Journals and magazines, two-column format single column 20 3¼ 8¼ double column 42 7 17½ single column 13 2 5 double column 27½ 4½ 11 triple column 42 7 17½ Magazines, three-column format • For a printed publication, you can determine the column width and page length by measuring a sample copy of the journal or a similar book from the same publisher. • For ACS journals, try to design ﬁgures to ﬁt the width of one column. Table 15-2 gives the column widths and page lengths of many ACS publications. • Do not put unnecessary frames or boxes around your ﬁgures. • Remember that the length that you measure or take from Table 15-2 is the maximum space available for the ﬁgure plus captions or notes. Therefore, the art must be small enough to leave space for the caption. • Finally, the width and depth of a ﬁgure should not exceed the needs of that ﬁgure. Be economical; do not waste space. Working with Line Art If you are creating line-art ﬁgures with a computer program, save them in an appropriate format (see Table 15-1) or print them on white, high-quality, smooth, laser-printer paper and scan them. If line-art ﬁgures are being drawn by hand, use black ink on white, high-quality, smooth, opaque paper, and then scan them. Box 15-4 provides tips for successful scanning. Here are some ways to improve the quality of the line-art ﬁgures you submit: ➤ Select software that will yield the best results for the line art you wish to create. Chapter 15: Figures ➤ 355 ➤➤➤➤➤ Box 15-4. Tips for Successful Scanning • If possible, use a ﬂatbed scanner, where the art rests ﬂat on a glass surface and is scanned by a moving scanner’s eye, rather than a sheet-fed scanner, where the art is rolled past the scanner’s eye. Flatbed scanners are less likely to distort your ﬁgure. • Use your scanner’s optical (that is, actual) resolution capability, not the interpolated (that is, calculated) one. • Scan photographs at a minimum resolution of 300 ppi. • Scan line art at a resolution of minimum 600 ppi, but 800, 1000, or 1200 ppi is even better. (Line art for ACS publications must be 1200 ppi.) • If possible, determine the ﬁnal size of your ﬁgure in print and calculate the percentage of expansion or reduction. Then scan the photograph at that percentage. • If you are not sure about the ﬁnal size, scan your photograph at a larger size (say, 150% with 300 ppi) or higher resolution (say, 100% with 450 ppi). Scan your line art at 150% with 600 ppi or at 100% with 1000 ppi. It is better to submit image ﬁles with too much information than too little. • Do not adjust contrast or color according to what you see on your monitor. Instead, use the automatic adjustments that come with the scanning software or use the calibration curves that come with image-editing software, such as Photoshop. • Do not apply any screening in the scanning or editing software, even if you know the ﬁgure will be screened before it is published. Let the publisher and the publisher’s printer determine the appropriate screening. ➤ Create the line art to the exact size at which it will be published. ➤ Keep line-art ﬁgures clear and simple. Keep words to a minimum. Lengthy explanations should go in the caption or a note accompanying the caption. ➤ Scale the length, width, type, symbols, and lines of the art proportionally; keep the symbols, lines, and type at uniform density, or darkness. • Make the lines at least 0.5 point wide and usually not more than 1.5 points wide. 356 ➤ The ACS Style Guide ➤➤➤➤➤ Box 15-5. Type Size and Font In publishing, type is measured in points; space is measured in picas. There are 72 points to an inch; there are 6 picas to an inch. The size of the type you are reading on this page is 10 points. The column is 28 picas wide, and the text page is 44 picas long. You can use a pica ruler to measure space, but it is hard to ﬁnd a type gauge for measuring type; you must compare it to known type sizes. For example, in 10 point type, no character actually is 10 points high. The font (or typeface) is the style or design of the letters. There are literally hundreds of fonts, but plain, simple fonts such as Helvetica or Times Roman are best for scientiﬁc art. Type also comes in different weights. Most of the type you are reading is lightface; this is boldface type. Type may be italic or roman. Generally, you should use lightface, roman type for ﬁgures. 14 This is 12 point Times Roman. C6H6 shows subscripts and superscripts. This is 12 point Helvetica. C6H6 shows subscripts and superscripts. 14 This is 14 point Times Roman. C6H6 shows subscripts and superscripts. 14 This is 14 point Helvetica. C6H6 shows subscripts and superscripts. 14 • Select a type size of 7–10 points; for ACS journals, select a type size of 5–6 points. • Make the symbols at least the size of a lowercase letter “oh” (about 2 mm) (see Box 15-5). • Use a clear type font, preferably Helvetica or Times Roman (see Box 15-6). • Disparities between the size of the type and the symbols make for illegible or unattractive art; if the type is the right size, the symbols will appear too small or too large, and vice versa. Likewise, the proportion between the overall size of the ﬁgure and the type and symbols should be appropriate (see Figure 15-2). ➤ Use simple, common symbols that would not be confused with each other and would be readily available in any publishing house, for example, , , , , , , , , , , +, ×, , and . (Even if you provide a legend within the ﬁgure, you may wish to refer to the symbols in your text.) Chapter 15: Figures ➤ 357 ➤➤➤➤➤ Box 15-6. Tips Regarding Fonts The fonts used to create some types of electronic ﬁgure ﬁles occasionally cause problems for publishers, in both print and Web publications. The problems can include character substitution, distorted spacing between letters, and copyright infringement. The software behind a font is covered by copyright law. Whereas some copyright holders allow open access to their fonts, others exercise some sort of limit. Publishers respect the copyright on fonts and will not use a font without proper permission. Only some electronic ﬁles embed font software in the ﬁles. • • GIFs, TIFFs, JPEGs, and other pixel-based ﬁles embed only the images of letters, not the font software itself, in their ﬁles. Type in these ﬁles can be erased, but it is not truly editable. EPS and PDF ﬁles must have font software fully embedded to be usable. Type in these ﬁles is fully editable. TrueType is a font format designed by Microsoft for maximum legibility on a computer monitor, and it prints well on dot-matrix, inkjet, and laser printers. Microsoft permits free use of the fonts it provides (such as Times New Roman and Arial), but other companies that provide TrueType fonts may have use restrictions. TrueType fonts perform well in Web publishing, but they often pose technical problems in print publishing. TrueType fonts are ﬁne for producing GIFs, TIFFs, and JPEGs, as well as PDFs intended for the Web. PostScript is a font format designed for high-end graphic arts. These fonts are designed for maximum legibility on paper and for maximum compatibility with high-quality, high-output printing equipment. PostScript fonts are generally covered by copyright and have limitations on their use. They seldom pose technical problems in print publishing, but the copyright issues may limit their usefulness in Web publishing. PostScript fonts are best for EPS ﬁles and PDFs intended for print. OpenType fonts are a relatively new format intended to combine the virtues of both TrueType and PostScript fonts. STIX (scientiﬁc and technical information exchange) fonts were developed by a group of six scientiﬁc publishers to establish a comprehensive set of fonts that contains essentially every character that might be needed to publish a technical article in any scientiﬁc discipline. STIX fonts are available as a free download, under license, at www.stixfonts. org. A white paper by Tim Ingolsby on the STIX fonts project is available at www.aipservices.org/newsroom/white_papers/pdf/STIX-fonts.pdf. 358 ➤ The ACS Style Guide A � � Cl � �F 2.0 Log k 1.5 1.0 0.5 0.0 � � –0.5 –1.0 –1.5 –2.0 –2.5 –0.2 B OTs Br 2.5 �� –0.0 � 0.2 0.4 σ∗ 0.6 0.8 1.0 1.2 2.5 1.5 Cl� � F 1.0 Log k OTs � Br � 2.0 1.4 0.5 0.0 � � –0.5 –1.0 –1.5 –2.0 � � –2.5 –0.2 –0.0 � 0.2 0.4 0.6 σ∗ 0.8 1.0 1.2 1.4 Figure 15-2. (A) Example of a poorly rendered line graph, with lines that are too thin, a type font that is too ornate, and type and symbols that are sized disproportionally to the figure. (B) Example of the same line graph properly rendered. Source: Adapted from Alunni, S.; De Angelis, F.; Ottavi, L.; Papavasileiou, M.; Tarantelli, F. J. Am. Chem. Soc. 2005, 127, 15151–15160. Copyright 2005 American Chemical Society. ➤ Lines may be differentiated by the use of varying line styles, such as solid, dashed, dotted, and various weights (but never less than 0.5 point wide). ➤ You may combine curves plotted on the same set of axes, but do not put more than ﬁve curves in one ﬁgure. (If you have more than ﬁve curves, consider splitting the ﬁgure into two parts or two separate ﬁgures.) Label all curves clearly. Leave sufﬁcient space between curves; they should not overlap so much that they become indistinguishable. Chapter 15: Figures DEPOSITION A 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ➤ 359 total wet dry ONTARIO LAKE ERIE LAKE HURON MICHIGAN SUPERIOR LAKES B Deposition (kg/yr) 8 Total 7 Wet 6 Dry 5 4 3 2 1 0 Ontario Erie Huron Michigan Superior Lakes Figure 15-3. (A) Example of a poorly rendered bar graph, with excess white space at the top, shading that is difficult to distinguish, and poor and incomplete labels. (B) Example of the same bar graph properly rendered. Source: Adapted from Ma, J.; Venkatesh, S.; Li, Y.-F.; Daggupaty, S. Environ. Sci. Technol. 2005, 39, 8123–8131. Copyright 2005 American Chemical Society. ➤ Keep line-art ﬁgures compact; draw axes only long enough to deﬁne the contents. For example, if the highest data point on the curve is 14, then the scale should extend no longer than 15. Furthermore, the origin or lowest point on the axes does not have to be zero. For example, if the lowest data point on the curve is 4, then the axis can start at 3. Put grid marks on the axes to indicate the scale divisions. ➤ Use complete and consistent axis labels (see Figure 15-3). • Label each axis with the parameter or variable being measured and the units of measure in parentheses. 360 ➤ The ACS Style Guide • Use initial capital letters only, not all capitals: Time (min), Reaction Temperature (°C), Thickness (µm). • Place all labels outside and parallel to the axes. Numbers and letters on the abscissa and ordinate should read from left to right and from bottom to top, respectively. • Do not place arrowheads on the ends of the axis lines. • Label the tick marks on an axis in type that is one or two points smaller than the axis labels (but not smaller than 7 points in general, 5 points for ACS journals). ➤ Do not draw a box around line-art ﬁgures. ➤ For insets, labels, or legends within the ﬁgure, use initial capital letters and use the same size type as for the axis labels. ➤ Save electronic ﬁgure ﬁles with a minimum of white space around the edges. ➤ If you are printing line-art ﬁgures for subsequent scanning, always check that the toner or ink cartridge is fresh, and never use a dot-matrix printer. ➤ If you print a hard copy to submit with the electronic ﬁle, print it with one ﬁgure per page and be sure that the ﬁgure number appears on the page. Working with Photographs and Other Halftone Figures Good reproduction of photographs begins with good photographs. When you are selecting photographs for ﬁgures to accompany your text, consider the following points: ➤ As much as possible, the photograph should show what is important to your text, and only what is important. Clutter and unrelated objects should be cropped out. (This is easy to do with electronic images.) ➤ Photographs always lose some detail in reproduction, so be sure to take the photograph in good focus and, for digital photographs, with sufﬁcient resolution. See Figure 15-4. ➤ Photographs in print will tend to lose contrast and become muddy or gray, so take a few steps to ensure that your photograph has good contrast and tonal deﬁnition: • Adequately light objects that you are photographing. • Place objects on light or dark backgrounds that are plain or solid. Chapter 15: Figures ➤ 361 A B Figure 15-4. (A) Example of a photograph with a resolution that is too low for print, so the pixels show as squares, instead of blending to show tones. (B) A similar photograph with a true resolution of 300 ppi. Source: Adapted from Balss, K. M.; Avedisian, C. T.; Cavicchi, R. E.; Tarlov, M. J. Langmuir 2005, 21, 10459–10467. Copyright 2005 American Chemical Society. • Take several photographs at different settings, so that you can select the one with the best contrast and tonal deﬁnition. ➤ Photographs can have tricky copyright and permissions issues. Be sure you understand whether permission is needed to publish the photograph. (See the section called “Common Misconceptions about Copyright” in Chapter 7.) ➤ If you are scanning photographic prints, see Box 15-4. ➤ If you are using a digital camera, select a setting that collects enough digital information. The lowest setting might be sufﬁcient for GIFs, but the higher settings will be necessary for print publication. 362 ➤ The ACS Style Guide When you are working with the electronic ﬁles of photographs and other halftones, keep the following in mind: ➤ Do not adjust the ppi upward without adjusting the overall dimensions downward. Simply changing the ppi setting from 72 to 300, even if your software allows it, does not put digital information in that was not there before. The ﬁle might indicate that the resolution is 300 ppi, but the art will still print as fuzzily as a 72 ppi picture. ➤ You can adjust the ppi downward without changing the overall dimensions. This throws away information that is not necessary and makes a ﬁle more portable if, for instance, you scanned at a higher resolution because you were not sure how much you would crop it. ➤ You can switch from RGB to CMYK color modes and vice versa. ➤ If you switch from either RGB or CMYK to B&W, you will probably need to adjust the contrast of your photograph to get the black areas black and the white areas white. If you are providing photographic prints instead of electronic ﬁles, the following points are important to remember: ➤ Submit a good-quality photographic print, preferably not the only original you have. Some publishers try to return original art, but many do not. ➤ Label photographs by writing on an adhesive label (such as a mailing label) ﬁrst and then applying the label to the back of the photograph, or by writing on a separate sheet of paper and taping it to the back. Writing directly on the back of the photographic print might damage the front: ballpoint pens can break the smooth surface of the photograph, and felt tip pens can bleed through. ➤ Handle photographs with care. Most ﬂaws on a photographic print will be reproduced in the published photograph. You can damage photographs by paper clipping, folding, stapling, or using tape on them. Depending on the amount and location of the damage, you might have to reprint the photograph. ➤ Do not submit prescreened illustrations, that is, illustrations that were scanned from a print source (which is already screened) or scanned using a screen setting. ➤ Do not submit color prints to be reproduced in black and white. Use a professional photo lab to prepare B&W prints from color originals because photo labs use special paper to make B&W prints from color originals. Chapter 15: Figures ➤ 363 Working with Grayscale Line Art Grayscale line art for print publication of such ﬁgures as pie charts, bar graphs, and area graphs should be submitted only in an electronic format, preferably EPS. EPS ﬁles use mathematical formulas to produce lines and shading, so lines and type are never screened, and gray areas are screened only when the printing plates are made. (Rescreening screened art creates a distortion called moiré.) As a result, the lines in EPS ﬁles remain crisp even when the gray tones have been screened. ➤ Always fully embed the fonts or the font outlines in an EPS ﬁle. Otherwise, a different font may be substituted at the publisher’s, with unsatisfactory results. Be sure that you have rights to embed the font—you will be safest if you use Times Roman or Helvetica. ➤ Use screen shadings that are different by at least 20 percentage points. For example, you could ﬁll in the sections of a bar graph with 10%, 30%, 50%, 70%, and 100% black. (0%, 20%, 40%, 60%, 80%, and 100% also work well.) ➤ If you choose to screen lines within a line graph (never the axes), assign the lines a 1.5 or 2 point weight, and do not use symbols to mark points on the lines. Working with Combinations of Type and Photographs As mentioned in the earlier section, “Types of Figure Artwork”, a photograph that has a simple measuring scale or a few single-letter labels can be adequately handled like other halftones. However, if the photograph (or other halftone artwork) must be accompanied by text to convey meaning, then you should prepare a combo. One way to do this is to prepare the photograph as a grayscale or color TIFF and then import the photographic image ﬁle into a drawing program, such as Illustrator or Freehand. Use the drawing program to add type, lines, axes, tick marks, and so on, and save the ﬁle as an EPS with an embedded TIFF. An alternative is to create the combo in a word-processing program, such as Word or WordPerfect, and then export the page as a PDF ﬁle. Simply assembling the type and photograph in the word-processing program and submitting the application (.doc or .wpd) ﬁle is seldom acceptable to publishers other than ACS journals. How To Submit Illustrations If you follow the recommendations presented in this chapter, you should be well on your way to trouble-free submission of your ﬁgure ﬁles. Keep the following points in mind for submitting to publishers other than ACS journals. 364 ➤ The ACS Style Guide Publishing with ACS: For manuscripts submitted to ACS journals through Paragon, illustrations should always be embedded in the text document before submission—that is, illustrations should not be submitted as separate ﬁles from the text. Illustrations submitted through the Paragon Plus environment can be embedded in the text or supplied separately. Before being embedded, however, the illustrations should be prepared outside the word-processing program to the correct size and resolution as recommended in this chapter. Each illustration should be “inserted” (not “pasted”) into the text document so that it maintains its original resolution, and it should not be adjusted for size after insertion. Graphics taken from Web sites should not be used because, at 72 ppi, their resolution is not adequate for print publication. For All Figures ➤ Submit a clean photocopy or printout of all ﬁgures to accompany your manuscript. ➤ Unless a publisher instructs otherwise, do not put the ﬁgures in the midst of text; put them on separate pages at the end. ➤ Put one ﬁgure on each page, and label the page with the ﬁgure number only. Submit captions as part of your text. For Electronic Files ➤ Be sure that the art is oriented correctly in the ﬁle. ➤ The ﬁle name should be brief and consistent, preferably something like Smith_ﬁg02.tiff or Jones_chap5_ﬁg10.eps. ➤ Unless the publisher requests that you submit via a Web site, write the ﬁles to a CD, DVD, Zip disk, or 3.5 in. ﬂoppy disk. Label the disk with the author name, manuscript title, and general contents, such as manuscript number, ﬁgures, tables, and so on. For Camera-Ready Art ➤ Note the ﬁgure number and the ﬁrst author’s surname either on the back or on the front of each piece of artwork, about 1 in. (2.5 cm) clear of the image area. Do not write on the front or back of the image area; write only in the margins. ➤ Indicate the top of the illustration with the word “top” if the correct orientation is not obvious. Chapter 15: Figures ➤ 365 ➤ Do not fold or roll artwork or photographs; protect art with cardboard or heavy paper for transport. Do not staple, clip, or punch holes in photographs or any artwork. How To Prepare Figure Captions Every ﬁgure must have a caption that includes the ﬁgure number and a brief, informative description, preferably in nonsentence format. good examples of figure captions Figure 2. Mass spectrum obtained when laboratory ambient air containing 2.5 ppm of 1 was introduced into the MS system. Figure 4. Change in carotenoid contents during maturation of three varieties of grapes: (A) Concord grapes; (B) Thompson seedless; and (C) Chilean red. Figure 6. Variable-temperature NMR spectra of 3d in CD2Cl2 solution at 500 MHz. Figure 7. Reaction rate constants as a function of proton afﬁnity for the reactions shown in eqs 5–7: kexp, experimental; kc, calculated. Figure 1. Speciﬁcity of bovine muscle LDH antibodies in a sandwich ELISA. Data represent the averages of three replicates. If more information is necessary, use complete sentences and standard punctuation. The caption should be understandable without reference to the text (this is essential in Web publishing because the figure may open in a separate frame) and should not include material that is at odds with the text. Use similar wording for captions of related figures. If a ﬁgure contains symbols that require long explanations or has more than four or ﬁve symbols, then the key to the symbols will be large and give the artwork a cluttered appearance. In this case, put the key to the symbols in the caption. Make sure that the symbols and abbreviations in the caption agree with those in the ﬁgure itself and in the text and that the symbols are typographically available. Submit the ﬁgure captions separately from the artwork, typed double-spaced on a page at the end of the text. Verify that the numbers in the caption agree with the numbers on the ﬁgures and in the electronic ﬁle names. Bear in mind that ﬁgures and captions are handled differently in both Web and print production; captions are usually typeset in a font and size that follow the style of the publication, whereas ﬁgures are used as is. If you place the caption on the art, the editors usually will delete it and have the caption typeset according to the publication’s style. At best, this creates additional work and an opportunity for errors to occur; at worst, the presence of captions with the text and on the art may cause confusion if they are inconsistent. 366 ➤ The ACS Style Guide Reproducing Previously Published Materials To reproduce a ﬁgure, photograph, or table that has been published elsewhere, you (the author) must obtain permission in writing from the copyright owner (usually the publisher), and you must submit the written permissions along with your ﬁnal manuscript. Even if you were the author of the previously published ﬁgure or table, you still need written permission from the copyright owner. The only exception is for a work of the U.S. government. See Box 15-7 for examples of credit lines. See also Chapter 7, “Copyright Basics”, for further information. ➤ If you construct a ﬁgure or a table from data that were previously published as text or use data from a table to create an original ﬁgure, you do not need permission, but you should reference the source of the data (e.g., “Data are from ref 7.”). However, if you are using a portion of a table that has been previously published, even very small portions such as a few data points, permission is needed from the copyright holder. ➤ If you adapt or use only part of a ﬁgure or table, permission is still needed. The credit line for adapted material is similar to the credit lines in Box 15-7 except “reprinted” is replaced with “adapted”. Adapted with permission from ref XX. Copyright Year Copyright Owner’s Name. Adapted with permission from Author Names (Year of Publication). Copyright Year Copyright Owner’s Name. ➤ If you are thinking about using a previously published ﬁgure or table, consider carefully whether citing it as a reference would be adequate. Chapter 15: Figures ➤ 367 Box 15-7. Credit Lines in ACS Publications In ACS publications, credit lines for art reproduced from previously published work appear at the end of the caption in parentheses in one of two formats and follow three possible wordings, depending on the original source: Format 1 Most publishers: Reprinted with permission from ref XX. Copyright Year Copyright Owner’s Name. Reprinted with permission from ref 10. Copyright 2003 American Pharmaceutical Association. Published by ACS: Reprinted from ref XX. Copyright Year American Chemical Society. Reprinted from ref 12. Copyright 2005 American Chemical Society. Published by the U.S. government: Reprinted from ref XX. Reprinted from ref 23. Format 2 Most publishers: Reprinted with permission from Author Names (Year of Publication). Copyright Year Copyright Owner’s Name. Reprinted with permission from Camiola and Altieri (2006). Copyright 2006 American Institute of Physics. Published by ACS: Reprinted from Author Names (Year of Publication). Copyright Year American Chemical Society. Reprinted from Fitzgerald and Cheng (2004). Copyright 2004 American Chemical Society. Published by the U.S. government: Reprinted from Author Names (Year of Publication). Reprinted from Takanishi and Schmidt (2006). Be sure to check the author guidelines for your publication. ➤➤➤➤➤ CHAPTER 16 Tables Betsy Kulamer T his chapter presents guidelines for preparing the tables that accompany a scientiﬁc paper for publication. Tables are handled in many ways like ﬁgures, so this chapter focuses on the ways in which tables are different and brieﬂy discusses the preparation of tables using wordprocessing programs. When To Use Tables Use tables when the data cannot be presented clearly as narrative, when many precise numbers must be presented, or when meaningful interrelationships can be better conveyed by the tabular format. Tables should supplement, not duplicate, text and ﬁgures. (If you are not sure whether you need a table or ﬁgure, see Box 15-1.) Examples of material that is best handled as narrative in text are results of IR absorption and NMR chemical shift studies, unless they are major topics of discussion. In many instances, one table with representative data, rather than several tables, is all that is needed to convey an idea. How To Cite Tables Like ﬁgures, all tables must be called out, that is, mentioned or discussed by name and number in the text. ➤ Capitalize the word “Table” when it is followed by the table number. ➤ Number tables sequentially with arabic or roman numerals, depending on the publication’s style, in order of discussion in the text: Table 2 or Table IV. Copyright 2006 American Chemical Society 369 370 ➤ The ACS Style Guide ➤ Discuss tables sequentially, so that Table 1 is discussed before Table 2, Table 2 before Table 3, and so on. For good examples of a callout in text, see Chapter 15, Figures, pp 345–346. How To Prepare Tables There are two kinds of tables: informal (or in-text) and formal. An informal table consists of three to ﬁve lines and is no more than four columns wide; it cannot exceed the width of a text column. Informal tables may be placed in text following an introductory sentence, and each column should have a heading. They are not given titles or numbers, nor do they contain footnotes. A formal table should consist of at least three interrelated columns and three rows. If you have only two columns, try writing the material as narrative. If you have three columns, but they do not relate to each other, perhaps the material is really a list of items and not a table at all (see the discussion of lists at the end of this chapter). If your table has unusual alignment and positioning requirements, perhaps it should really be a ﬁgure. It is important to understand these differences because tables are more expensive to produce than text; the larger the table, the higher the cost. A well-constructed, meaningful table is worth the expense, but anything else is wasteful and does not enhance your paper. Tables should be simple and concise; arrange all data for optimal use of space. If you have many small tables, consider combining some. Combining is usually possible when the same column is repeated in separate tables or when the same type of material is presented in several small tables. Use consistent wording for all elements of similar or related tables. Be consistent with symbols and abbreviations among tables and between tables and text. ➤ The table width will depend on the widths of its individual columns. • Generally, tables having up to 6 columns will ﬁt in a single journal col- umn; tables having up to 13 columns will ﬁt in the double-column spread. Tables that exceed the double-column spread will be rotated 90° and set lengthwise on the page. • In books, tables having up to 8 columns can ﬁt in the page width; tables having 9–12 columns will be set lengthwise on the page. Larger tables can span two pages. • In all publications, extremely wide tables can cause composition difﬁculties. In such cases, consider presenting the material as two or more smaller tables. ➤ The style for the individual parts of tables (i.e., the use of capital and low- ercase letters and whether the entries are centered or ﬂush left) varies among publications. Consult a recent edition of the journal or the journal’s instructions for authors. Chapter 16: Tables ➤ 371 ➤ Keep sections of multipart tables at similar widths. Widely divergent section widths within a table waste space and detract from general appearance. Effective tables are well-designed, so think carefully, first, about the data you need to present and, second, about the best way to present it visually on a page. Sometimes, what looks fine on a letter-size sheet of paper is not practicable for a journal or book page. Sometimes, what you originally conceived as the column headings works better as the row headings. (In general, you should have more row headings than column headings.) Understanding the parts of a table will help you design your tables effectively; they are identified in Figure 16-1. Title ➤ Give every formal table a brief, informative title that describes its contents in nonsentence format. The title should be complete enough to be understood without referring to the text. Place details in table footnotes, not in the title. ➤ Begin the table title with the word “Table” and its number, and then continue with the title. Column Headings Every column must have a heading that describes the material below it. A column heading should not apply to the entire table; information that describes all of the columns belongs in a general table footnote. If a column heading applies to more than one column, use a rule below it that spans the columns to which it applies; this is called a straddle rule. Below the rule, give the speciﬁc headings for each column. A unit of measure alone is not an acceptable column heading, unless the column heading appears under a straddle rule. ➤ Be as succinct as possible, keep column headings to two lines if possible, and use abbreviations and symbols whenever practical. ➤ Be consistent with the text and with other column headings. ➤ Deﬁne nonstandard abbreviations in table footnotes. Name the variable being measured, and indicate the unit of measure after a comma or slash or within enclosing marks. Use the same style within and among all tables. Column Entries In many tables, the leftmost column is the stub or reading column. Usually, all other columns refer back to it. Stub entries should be consistent with the text as well as logical and grammatically parallel. Main stub entries may also have subentries, which should be indented. 372 ➤ The ACS Style Guide Column Table headings title Stub column Straddle head Table 2. Conditioned WRA and Mechanical Strength of Plain-Weave Cotton Fabric Treated with Different Cross-Linking Agentsa Cross-Linker Concentration WRA (deg, w + f) No. Catalyst Curing of Laundering Cycles Flex Abrasion Retention Concentration Condition 1 5 10 20 (no. of cycles, warp) Unmodified Table text 8% PMA Dried 2% NaH2PO2 180 ˚C, 1.5 min 273 261 261 260 309 Soaked 3% NaH2PO2 182 ˚C, 1.3 min 274 260 260 262 310 6% BTCA 4% NaH2PO2 180 ˚C, 1.5 min 287 276 273 270 148 10.5% modified precatalyzed DMDHEU 165 ˚C, 1.5 min 278 273 269 264 68 control 180 ˚C, 1.5 min 190 Table footnote Modified 868 a The concentrations of PMA, BTCA, and NaH2PO2 are calculated on the basis of 100% active ingredient; the concentration of DMDHEU is based on the weight of the commercial product, which contains 55% solid. The wet pickup of the treated fabric is approximately 105–110%. Figure 16-1. Parts of a table. Source: Adapted from Chen, D.; Yang, C. Q.; Qiu, X. Ind. Eng. Chem. Res. 2005, 44, 7921–7927. Copyright 2005 American Chemical Society. ➤ Material in columns can be aligned in various ways; use only one type of alignment per column. Words are usually aligned on the left, and numbers are usually aligned on the decimals, unless they do not have the same units, in which case they are aligned on the left. Use numbers on both sides of a decimal point; numbers less than 1 should have a zero to the left of the decimal point. Columns that are made up of numbers and words together or columns that contain a variety of sizes or types of information might call for alignment on the left, right, or center, depending on the publication’s style. ➤ Do not use ditto marks or the word “ditto” to indicate the same entry in a column; repeat the entry. ➤ Deﬁne nonstandard abbreviations in table footnotes. ➤ Try to keep all entries at similar lengths by placing any explanatory material in table footnotes. If you use a dash as a column entry, explain it in a footnote the ﬁrst time it is used (e.g., “—, too low to be measured.”). ➤ Make sure that all of the columns are really necessary. If there are no entries in most of a column, it probably should be deleted and replaced with a general Chapter 16: Tables ➤ 373 table footnote. Alternatively, if the entries in the entire column are the same, the column should be replaced with an appropriate table footnote, such as “In all cases, the value was x.” Footnotes Table footnotes include explanatory material referring to the whole table and to speciﬁc entries. Examples of information that should be placed in general footnotes referring to the whole table are the following: units of measure that apply to all entries in the table, explanations of abbreviations and symbols used frequently throughout the table, details of experimental conditions if not already described in the text or if different from the text, general sources of data, and other literature citations. Information that should be placed in speciﬁc footnotes includes units of measure that are too long to ﬁt in the column headings, explanations of abbreviations and symbols used with only one or two entries, statistical signiﬁcance of entries, experimental details that apply to speciﬁc entries, and different sources of data. In some publications, such as books, general footnotes and sources are not cited with superscripts; they are labeled “Note” and “Source”, respectively. Speciﬁc footnotes are cited with superscripts. In other publications, all footnotes are cited with superscripts. Check the directions for the publication to which you are submitting your paper. ➤ Where superscripts are needed, use superscript lowercase italic letters in alpha- betical order, starting from the top of the table and proceeding from left to right. ➤ Write footnotes as narrative and use standard punctuation. Short phrases such as “ND, not determined.” and “x = 23.” are acceptable. ➤ Label each footnote with its superscript letter and group the footnotes together at the end of the table. All footnotes must have a callout in the table title or text. Using Word-Processing Software When you prepare your tables using word-processing software, a few techniques ensure a smoother transition to either Web or print publication. ➤ In Microsoft Word or WordPerfect, use the software’s table feature, rather than aligning columns using the tab key. Entries arranged with the table feature are more likely to be properly aligned in publication than entries that have been tabbed. ➤ Set up the table in 10 or 12 point type, although 8 point type can be used if necessary. If you need to use type smaller than 8 points to ﬁt your table on a letter-size page, it probably will not ﬁt comfortably on a book or journal page. ➤ Double-space the text in the table. 374 ➤ The ACS Style Guide ➤ When you use the table feature, put only one row of entries in each row of the table. Do not put multiple entries in a single cell by using the hard return. ➤ Avoid using hard returns to add space between rows of the table. If you wish to show more space than is apparent with double-spacing, use the line formatting feature of the word-processing program instead. How To Submit Tables If you follow the recommendations presented in this chapter, you should experience trouble-free submission of your tables. Keep the following points in mind: ➤ Place formal tables after the references at the end of the text ﬁle, each on its own page. ➤ Place informal tables in place within the text. ➤ Submit a printout of tables along with the printout of text if the publisher requests one. ➤ If a table must contain structures or other art or special symbols, or if a table has special alignment and positioning requirements, be sure that these are evident on the printout. Publishing with ACS: In manuscripts submitted to ACS journals through Paragon, tables should always be embedded in the text document before submission, that is, tables should not be submitted as separate ﬁles from the text. Tables in manuscripts submitted through the Paragon Plus environment can be embedded in the text or supplied separately. When To Use Lists Sometimes you may need to give numerous examples of items, such as chemical names. In such cases, if there are too many to run into the text, they can be set as a list in some publications. Put the entries in alphabetical order, unless there is a reason to do otherwise. A list of names is not truly a ﬁgure and not really a table. Give the list an unnumbered title. In ACS journals, lists may be handled as informal tables or even as charts. potentially carcinogenic medicines azacitidine azathioprine chloramphenicol chlornaphazine cyclophosphamide cytarabine dacarbazine ﬂuorouracil methotrexate nitrofurazone phenacetin phenoxybenzamine ➤➤➤➤➤ CHAPTER 17 Chemical Structures Antony Williams T he communication of chemical structures is inherently visual, so the language of both chemistry and biochemistry would be sparse without the ability to accurately represent chemistry in a graphical format. Scientiﬁc manuscripts today beneﬁt from the visually appealing output of software used to generate structure representations conveying the details of molecular connectivity as well as the details associated with chemical structures, reactions, and schemes. This chapter discusses the use of chemical structures; the related reactions, charts, and schemes, in a scientiﬁc manuscript; and methods of preparing and submitting structures for publication. The chapter presents general guidelines; authors should consult with their publishers for speciﬁc instructions. When To Use Structures A chemical structure is a pictorial representation of the bonding of atoms in a molecule. Chemical structures appear within text at the point at which they are discussed. Structures are numbered sequentially with either arabic or roman numerals; consult the publisher’s guidelines to determine if one is preferred over the other. Generally, there is no need to provide graphical representations of structures for materials that can be accurately represented on one line or in the form of text. For scientiﬁc publications, structures should be included for clarity of communication only. For example, papers describing previously unreported syntheses or reaction sequences, structure–activity relationships, or newly discovered chemical compounds make good use of chemical structure images. Simple chemical strucCopyright 2006 American Chemical Society 375 376 ➤ The ACS Style Guide O O O O H O HN O OH OH HO O O O O O Figure 17-1. Example of a chemical structure. tures can often be represented by a line formula, such as C6H5COOH or 1,2,4Br3C6H3, or by the systematic name of the compound, such as benzoic acid or 1,2,4-tribromobenzene, but complex chemical structures depend on structural representations exhibiting the atom–atom connectivity, including the order and stereochemistry of the bonds. Even though a systematic name can accurately describe the chemical structure of paclitaxel, speciﬁcally, (2aR,4S,4aS,6R,9S, 11S,12S,12aR,12bS)-6,12b-diacetoxy-9-{[(2R,3S)-3-(benzoylamino)-2-hydroxy3-phenylpropanoyl]oxy}-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a, 5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2b]oxet-12-yl benzoate), most chemists would prefer to visualize the structure (shown in Figure 17-1). ✐ Reminder: Simple chemical structures can often be represented by a line formula or by the systematic name of the compound, but complex chemical structures depend on structural representations exhibiting the atom–atom connectivity, including the order and stereochemistry of the bonds. A chemical reaction is a pictorial representation of a change or process. Reactions can be represented with either line formulas or structures; they are placed in text and numbered much like mathematical equations. See pp 272–274 of Chapter 13 for information on how to format chemical reactions. Groups of structures are called charts. Charts contain representations of multiple structures to facilitate discussion of them. Groups of reactions are called schemes; as shown in Figure 17-2, several reactions can be presented together to show, for example, a step-by-step process. Schemes show action; charts do not. How To Cite Structures ➤ Structures are identiﬁed in text with boldface numerals (either arabic or roman), boldface alphabet letters (capital or lowercase), or a combination of Chapter 17: Chemical Structures ➤ 377 Scheme 1 Sn (Closed form) <2 ps S0* (EZZ, ZEZ, EEZ) ≈ 20 ps hν Ph Ph H Ph Ph ∆ Ph O Closed form ∆ Ph HO EZZ (sub ns) O ZEZ (730 ns) hν ∆ ∆ H EZE, ZEE, EEE (>1 ms) Ph Ph O EEZ (48 µs) Major isomer Figure 17-2. Example of a scheme representing a group of reactions. Representing work reported by Kodama, Y.; Nakabayashi, T.; Segawa, K.; Hattori, E.; Sakuragi, M.; Nishi, N.; Sakuragi, H. J. Phys. Chem. A 2000, 104, 11478. these. (These numbers should also appear as labels on the structures themselves.) For several structures or for a series of structures, use a consistent sequence of labels. Typical series may include the following: 1, 2, 3 I, II, III A, B, C a, b, c 1a, 1b, 1c Ia, Ib, Ic 1A, 1B, 1C IA, IB, IC If a compound is mentioned several times within the text, refer to it only by its label (e.g., “as shown by the reaction with 9”). Do not include or label structures that are not discussed in the text. ➤ Chemical reactions set as equations should be labeled with lightface roman letters, numerals, or combinations in parentheses in the right margin (see Chapter 13). Depending on the text, it may be appropriate to use one set of labels for both chemical reactions and mathematical equations, or two separate and distinct numbering sequences (for instance, eqs 1, 2, 3, … and reactions I, II, III, …). The numbering sequences for structures and for reactions should always remain separate. ✐ Reminder: If a compound is mentioned several times within the text, refer to it only by its label. ➤ Charts are numbered consecutively as Chart 1, Chart 2, and so on, with either arabic or roman numerals. Charts should be labeled with “Chart” and a number; they also may have brief titles and footnotes. 378 ➤ The ACS Style Guide ➤ Schemes are numbered consecutively as Scheme 1, Scheme 2, and so on, with either arabic or roman numerals. Schemes should be labeled with “Scheme” and a number; they also may have brief titles and footnotes. How To Prepare Structures The quality and size requirements for structures (and, by extension, reactions, schemes, and charts) are similar to those for other illustrations (see Chapter 15). The requirements associated with the representation of structures are supported by most of the software programs for drawing chemical structures (described in Box 17-1). The following guidelines should be used when creating the graphics for chemical structures. ➤ Arrange structures in horizontal rows within the width of a column. ➤ Make the size of the rings and the size of the type proportional. The published size of six-membered rings should be approximately ¼ in. (6.35 mm) in diameter; the published size of ﬁve-membered rings should be slightly smaller. The type size should be 5–8 points. ➤ Keep oddly shaped rings and the shapes of bicyclic structures consistent throughout a manuscript. In multiring structures such as steroids, use partial structures that show only the pertinent points. ➤ In three-dimensional drawings, use dashed lines for lines in the background that are crossed by lines in the foreground to give a greater three-dimensional effect. Make lines in the foreground heavier, as shown below. ➤ Center the compound labels (either numbers or letters) just below the structures. If a series of related compounds are being discussed, draw only one parent structure, use a general designation (e.g., R or Ar) at the position(s) where the substituents differ, and specify modiﬁcations below the structure. ✐ Reminder: Take care that the structure graphic inserted into your text ﬁle is of sufﬁcient resolution, that is, 300 ppi minimum, with 600 or 1200 ppi even better. ➤ For structures mentioned in tables, provide labeled structures as separate art- work (in text or charts), and use only their labels in the table. Chapter 17: Chemical Structures ➤ 379 ➤ Center the reaction arrows vertically on the midline of the structure height and align the centers of all structures. The midline for all structures is the center of the “tallest” structure on the same line. An example of a correctly drawn reaction is represented below. As shown, the arrow and the one-line structure are centered, top to bottom, in the height of the full structure. The reaction arrow and the plus sign have an equal amount of space on both sides. O R4 O N OH + H N 2 R' R4 O N R' N H ➤ Do not waste space, either vertical or horizontal. Use the full column width before starting a new line. A compact presentation is most effective. Avoid using vertical arrows unless it is necessary to portray a cyclic or “square” reaction scheme. Schemes generally read from left to right. As long as the proper sequence is maintained, it does not matter on which line any given structure appears. If a reaction continues to the next line, keep the arrow or other operator on the top line. Refrain from the use of double-column-width charts or schemes unless absolutely necessary because these charts and schemes consume a signiﬁcant amount of space. ➤ Do not place circles around plus or minus signs. ➤ For most chemical structure drawing programs, it works best to use the copy-and-paste feature to insert the structure drawing into a Microsoft Word document. However, you should take care that the structure graphic inserted into your text ﬁle is of sufﬁcient resolution, that is, 300 ppi minimum, with 600 or 1200 ppi even better. The author bears the responsibility to ensure the appropriate insertion. Software for Creating Chemical Structures A number of chemical structure drawing and rendering programs are available to create structure images of excellent quality and accuracy for inclusion in scientiﬁc publications. The most popular commercial structure-drawing packages today include ISIS/Draw, ChemDraw, and ChemSketch (see Box 17-1). Other commercial packages include ChemWindow (now known as DrawIt) and Chemistry 4-D Draw. At this time, Web-based applets do not support the production of graphical output of sufﬁcient quality for most books and journals; other software, such as JMol, should be considered as structure-rendering engines only. Box 17-2 contains parameter settings for ACS publications. 380 ➤ The ACS Style Guide ➤➤➤➤➤ Box 17-1. Software for Drawing Chemical Structures The following is a selection of commercially available software for drawing chemical structures suitable for publication. ChemDraw: Cambridgesoft, 100 CambridgePark Drive, Cambridge, MA 02140. Commercial: http://www.chemdraw.com. Chemistry 4-D Draw: Cheminnovation, 7966 Arjons Dr, #A-201, San Diego, CA 92126. Commercial: http://www.cheminnovation.com/products/ chem4d.asp. ChemSketch: Advanced Chemistry Development, 110 Yonge Street, 14th Floor, Toronto, Ontario M5C 1T4, Canada. Commercial: http:// www.acdlabs.com/products/chem_dsn_lab/chemsketch/. Freeware: http://www.freechemsketch.com. DrawIt (formerly ChemWindow): Bio-Rad, Informatics, Sadtler Group, 3316 Spring Garden Street, Philadelphia, PA 19104-2596. Commercial: http://www.knowitall.com/. ISIS/Draw: Elsevier MDL, 14600 Catalina Street, San Leandro, CA 94577. Commercial: http://www.mdli.com/products/framework/isis_draw/index.jsp. Freeware: http://www.mdli.com/downloads/downloadable/index.jsp. MDL will ultimately discontinue ISIS/Draw and replace it with Mol Draw. The cost of these software packages can vary considerably based on academic or industrial usage. Fortunately, the cost should not be a barrier to the inclusion of appropriate renderings of chemical structures because several freeware structure-drawing packages are now available for download from the World Wide Web. These include freeware versions of both ISIS/Draw and ChemSketch. A detailed comparison of capabilities for both the freeware and commercial versions of the packages has been made by Tamas Gunda (http://dragon.klte. hu/~gundat/rajzprogramok/dprog.html). This review is an objective comparison, updated on an almost annual basis, of the capabilities of ﬁve popular drawing packages [ISIS/Draw, ChemDraw, DrawIt (ChemWindow), ChemSketch, and Chemistry 4-D Draw]. ✐ Reminder: The cost should not be a barrier to the inclusion of appropriate renderings of chemical structures because several freeware structuredrawing packages are now available for download. It is preferable to use one of the drawing packages that offer journal-based templates containing the appropriate bond widths, bond lengths, fonts, and Chapter 17: Chemical Structures ➤ 381 Box 17-2. Parameter Settings for ACS Publications At present, ACS journals request that chemical structures be prepared according to the guidelines below. (The guidelines are also available at https://paragon.acs.org/paragon/index.jsp. Click on “Read Author Information”, and then select the appropriate journal for speciﬁc information.) The parameters below are speciﬁcally for ChemDraw, using the ACS 1996 document settings; authors using other drawing packages should adapt these parameters to their systems. Most commercial and freeware packages allow these settings to be reproduced either by manual settings or by some sort of journal template feature. Drawing Settings Text Settings Preferences chain angle 120 degrees bond spacing 18% of width fixed length 14.4 pt (0.2 in.) bold width 2.0 pt (0.0278 in.) line width 0.6 pt (0.0083 in.) margin width 1.6 pt (0.0222 in.) hash spacing 2.5 pt (0.0345 in.) page setup US/Letter/Paper scale 100% font Helvetica (Mac), Arial (PC) size 10 pt units points tolerances 3 pixels other settings recommended by a particular journal. Using these templates aids in the production of a chemical structure drawing acceptable to the publishers. How To Submit Chemical Structures Many common graphical formats can be generated using structure-drawing packages, including TIFF, GIF, and BMP; follow the guidelines for submitting ﬁgures presented in Chapter 15. Also, because ﬁle formats continue to develop and the preferences of a given publisher can change, authors should check with the publisher’s or journal’s author guidelines for acceptable software and ﬁle formats. Box 17-3 shows guidelines for submitting structures to ACS journals. 382 ➤ The ACS Style Guide Box 17-3. Guidelines for Submitting Chemical Structures to ACS Journals • In manuscripts submitted to ACS journals through Paragon, structures should be embedded in text documents. In manuscripts submitted through the Paragon Plus environment, structures can be embedded in the text or supplied separately. • Submit graphical images of chemical structures to ACS journals as embedded TIFF ﬁles, using a resolution of 300 pixels per inch (ppi) for color and 1200 ppi for black-and-white images. • ACS journals accept application ﬁles (native formats) for several common software programs, including .skc ﬁles from ISIS/Draw and .cdx ﬁles from ChemDraw. • Information on submitting chemical structure connection tables is available at https://paragon.acs.org/paragon/application? pageid=content&mid=preferredsoftware.html&parentid= authorchecklist&headername=Preferred%20Software. • CML is accepted by the ACS Paragon System for submission of supporting information. The visual appeal of a structure or reaction can differ from one software package to another, so authors may wish to interchange data between programs to obtain the best graphical display required for publication. Such an interchange is normally performed using a speciﬁc format of the atom– atom connection table known as a molﬁle. (Information on the MDL molﬁle format is available at http://www.mdl.com/downloads/public/ctﬁle/ctﬁle.pdf.) Such collections may, for example, describe molecules, molecular fragments, substructures, substituent groups, polymers, alloys, formulations and mixtures, and unconnected atoms. Most chemical structure drawing software packages available today allow both import and export of a molﬁle. An alternative generic ﬁle format is CML, the chemical markup language, which takes advantage of the strength of Web-based technologies and is discussed in Chapter 8. The Future of Representing Chemical Structures Despite the vast array of tools available today for structure drawing and representation, each tool is lacking in some way for the representation of complete structure space. Small organic molecules have been well supported, but the needs Chapter 17: Chemical Structures ➤ 383 of the inorganic, organometallic, and polymer chemist have commonly lagged behind. Chemical structure drawing programs will continue to develop version by version as software vendors deliver an ongoing array of functionality for their customers. The need to introduce additional ﬂexibility for structure representation will be ongoing, speciﬁcally as standards are set for preferred drawing styles by organizations such as IUPAC. A scoping exercise initiated by the IUPAC commission has deﬁned the preferred drawing styles for structure representation to ensure accurate communication of chemical structures. (See http://www.iupac. org/projects/2003/2003-045-3-800.html. The stereo part of this project is now available as provisional recommendations at http://www.iupac.org/reports/ provisional/abstract05/brecher_310705.html.) It is likely that publishers will embrace the opportunity to standardize the structure representations within their publications to try to achieve greater homogeneity. Whereas chemical structures will always be the primary vehicle for visual communication, it is possible that journal articles will be reporting a unique label representing a chemical structure in the near future, especially because this label will already allow the searching of chemical structures contained in publications indexed using Web-based search engines. For more on this, see Appendix 8-1. ➤➤➤➤➤ CHAPTER 18 Selected Bibliography References on Scientiﬁc Communication Technical Writing Barrass, R. Scientists Must Write: A Guide to Better Writing for Scientists, Engineers, and Students, 2nd ed.; Routledge: London, 2002. Cook, C. K. Line by Line: How To Edit Your Own Writing; Houghton Mifﬂin: Boston, MA, 1986. Day, R. A. The Development of Research Writing. Scholarly Publishing January 1989, pp 107–115. Day, R. A. Scientiﬁc English: A Guide for Scientists and Other Professionals, 2nd ed.; Oryx Press: Phoenix, AZ, 1995. Eisenberg, A. Writing Well for the Technical Professions; Harper & Row: New York, 1989. King, L. S. Why Not Say It Clearly: A Guide to Scientiﬁc Writing, 2nd ed.; Little, Brown: Boston, MA, 1991. O’Connor, M. Writing Successfully in Science; Chapman & Hall: New York, 1992. Rathbone, R. R. Communicating Technical Information: A New Guide to Current Uses and Abuses in Scientiﬁc and Engineering Writing, 2nd ed.; Addison-Wesley: Reading, MA, 1985. Schoenfeld, R. The Chemist’s English, 3rd ed.; VCH: Weinheim, Germany, 1990. Shaw, H. Errors in English and Ways To Correct Them, 4th ed.; HarperPerennial: New York, 1993. Strunk, W., Jr.; White, E. B. The Elements of Style, 3rd ed.; Allyn & Bacon: New York, 1995. Zinsser, W. On Writing Well: The Classic Guide to Writing Nonﬁction, 6th ed.; HarperPerennial: New York, 1998. Zinsser, W. Writing To Learn; Collins: New York, 1993. Copyright 2006 American Chemical Society 385 386 ➤ The ACS Style Guide Style and Usage Bernstein, T. M. The Careful Writer: A Modern Guide to English Usage; The Free Press: New York, 1998. Berry, T. E. The Most Common Mistakes in English Usage; McGraw-Hill: New York, 1971. Copperud, R. H. American Usage and Style: The Consensus; Van Nostrand-Reinhold: New York, 1980. Flesch, R. F. The ABC of Style: A Guide to Plain English; HarperCollins: New York, 1980. Hodges, J. C.; Horner, W. B.; Webb, S. S.; Miller, R. K. Harbrace College Handbook, 13th ed.; Harcourt, Brace, Jovanovich: New York, 1998. Merriam-Webster’s Collegiate Dictionary, 11th ed.; Merriam-Webster Inc.: Springﬁeld, MA, 2003. (Available as a package with a CD and online; see http://www.m-w./com for information on the online product.) The New York Public Library Writer’s Guide to Style and Usage; Sutcliffe, A., Ed.; HarperCollins: New York, 1994. van Leunen, M.-C. A Handbook for Scholars, 2nd ed.; Oxford University Press: New York, 1992. Webster’s Third New International Dictionary, Unabridged; Merriam-Webster, Inc.: Springﬁeld, MA, 2002. (Available as a package with a CD and online; see http://www.m-w./ com for information on the online product.) Webster’s New World Dictionary of the American Language, 2nd ed.; Simon & Schuster: New York, 1980. Style Manuals AIP Style Manual, 4th ed.; American Institute of Physics: New York, 1990. American Medical Association Manual of Style, 9th ed.; Flanagin, A., et al., Eds.; Lippincott Williams & Wilkins: Baltimore, MD, 1997. ASM Style Manual for Journals and Books; American Society for Microbiology: Washington, DC, 1992. The Chicago Manual of Style, 15th ed.; University of Chicago Press: Chicago, IL, 2003. Merriam-Webster’s Standard American Style Manual; Merriam-Webster: Springﬁeld, MA, 1994. The Microsoft Manual of Style for Technical Publications, 3rd ed.; Microsoft Press: Redmond, WA, 2003. Publication Manual of the American Psychological Association, 5th ed.; American Psychological Association: Washington, DC, 2001. Scientiﬁc Style and Format: The CBE Manual for Authors, Editors, and Publishers, 6th ed.; Cambridge University Press: New York, 1994. Skillin, M. E.; Gay, R. M. Words into Type, 3rd ed.; Prentice-Hall: Englewood Cliffs, NJ, 1974. U.S. Government Printing Ofﬁce Style Manual 2000, 29th ed.; Government Printing Ofﬁce: Washington, DC, 2000. Wired Style: Principles of English Usage in the Digital Age; Hale, C., Ed.; HardWired: San Francisco, CA, 1997. Mathematics and Numbers Swanson, E.; O’Sean, A.; Schleyer, A. Mathematics into Type: Copy Editing and Proofreading of Mathematics for Editorial Assistants and Authors; American Mathematical Society: Providence, RI, 1999. Chapter 18: Selected Bibliography ➤ 387 Taylor, B. N. Guide for the Use of the International System of Units (SI); National Institute of Standards and Technology: Gaithersburg, MD, 1995. Preparing Illustrations Briscoe, M. H. Preparing Scientiﬁc Illustrations: A Guide to Better Posters, Presentations, and Publications, 2nd ed.; Springer Verlag: New York, 1996. Pocket Pal: A Graphic Arts Production Handbook, 18th ed.; Graphic Arts Technical Foundation: Alexandria, VA, 2000. References on Chemistry Conventions in Chemistry National Institute of Standards (NIST) Special Publication 330, 2001 Edition, Engl. version of The International System of Units (SI), 7th ed.; Bureau International des Poids et Mesures: Sèvres, France, 1998. http://physics.nist.gov/Pubs/SP330/sp330.pdf. Quantities and Units; International Organization for Standardization: Geneva, Switzerland, 1993. http://www.iso.org/iso/en/prods-service/ISOstore/store.html. Quantities, Units and Symbols in Physical Chemistry, 2nd ed.; Blackwell Science, Oxford, U.K., 1993 (commonly known as the “green book”). http://www.iupac.org. Biochemistry Biochemical Nomenclature and Related Documents, 2nd ed.; Liébecq, C., Ed.; Portland Press: London, 1992 (commonly referred to as the “white book”). http://www.chem. qmw.ac.uk/iupac/bibliog/white.html. Enzyme Nomenclature; Academic: New York, 1992. http://www.chem.qmw.ac.uk/iubmb/ enzyme/. Chemical Abstracts Advice on Chemical Abstracts nomenclature is available from the Manager of Nomenclature Services, Department 64, Chemical Abstracts Service, P.O. Box 3012, Columbus, OH 43210. A name-generation service is available through CAS Client Services, Chemical Abstracts Service, P.O. Box 3343, Columbus, OH 43210; e-mail address, answers@cas.org; and URL, http://www.cas.org/Support/client.html. Combinatorial Chemistry Maclean, D.; Martin, E. J. On the Representation of Combinatorial Libraries (A Perspective) J. Comb. Chem. 2004, 6, 1–11. Maclean, D.; Baldwin, J. J.; Ivanov, V. T.; Kato, Y.; Shaw, A.; Schneider, P.; Gordon, E. M. Glossary of Terms Used in Combinatorial Chemistry (IUPAC Technical Report) Pure Appl. Chem. 1999, 71, 2349–2365; Reprinted J. Comb. Chem. 2000, 2, 562–578; Translated to German Angew. Chem. 2002, 114, 893–906. Drug Names The USP Dictionary of USAN and International Drug Names; U.S. Pharmacopeial Convention: Rockville, MD, 2005 (updated annually). 388 ➤ The ACS Style Guide General Chemistry Chemical Abstracts Index Guide; American Chemical Society: Columbus, OH; Appendix IV (updated periodically). Compendium of Chemical Terminology, 2nd ed.; McNaught, A. D., Wilkinson, A., Eds.; Blackwell Science: Oxford, U.K., 1997. CRC Handbook of Chemistry and Physics, 86th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2005. Kirk-Othmer Encyclopedia of Chemical Technology, concise, 4th ed.; Wiley & Sons: New York, 2003. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed.; O’Neil, M. J., Smith, A., Heckelman, P. E., Budavari, S., Merck, Eds.; John Wiley & Sons: New York, 2001. Inorganic Chemistry Nomenclature of Inorganic Chemistry, Recommendations 2005; Connelly, N. G., Hartshorn, R. M., Damhus, T., Hutton, A. T., Eds.; Royal Society of Chemistry: Cambridge, U.K., 2005. Block, B. P.; Powell, W. H.; Fernelius, W. C. Inorganic Chemical Nomenclature: Principles and Practice; American Chemical Society: Washington, DC, 1990. Nomenclature The International Union of Pure and Applied Chemistry (IUPAC) Nomenclature Documents Home Page on the World Wide Web can be found at http://www.chem.qmw. ac.uk/iupac/. This site contains information on IUPAC itself, the names and publishers of references on chemical nomenclature, and many of the recommendations. Organic Chemistry IUPAC. Nomenclature of Organic Chemistry: Sections A, B, C, D, E, F, and H; Rigaudy, J., Klesney, S. P., Eds.; Pergamon: Elmsford, NY, 1979 (commonly referred to as the “blue book”). http://www.acdlabs.com/iupac/nomenclature. A Guide to IUPAC Nomenclature of Organic Compounds, Recommendations 1993; Panico, R., Powell, W. H., Richer, C., Eds.; Blackwell Scientiﬁc Publications: Oxford, U.K., 1994. http://www.acdlabs.com/iupac/nomenclature. Ring Systems Handbook; American Chemical Society: Columbus, OH, 2003 (and supplements). Fox, R. B.; Powell, W. H. Nomenclature of Organic Compounds: Principles and Practice, 2nd ed.; American Chemical Society: New York, 2001. Polymer Chemistry IUPAC. Compendium of Macromolecular Nomenclature; Blackwell Scientiﬁc Publications: Oxford, U.K., 1991. http://www.iupac.org/publications/books/author/metanomski. html. ➤➤➤➤➤ Index In page references, b indicates boxes, f indicates ﬁgures, s indicates schemes, and t indicates tables. “a” before collective nouns, 106 as gender-neutral alternative, 58 in titles, 149 See also Articles (part of speech) @ in e-mail addresses, 157 “a” and “b” references in reference lists, 297–298, 325 in text citations, 290 “a” vs “an” before element symbols, 257 general usage, 53 before isotopes, 257, 264 Abbreviations “a” vs “an” before, 53 in abstracts, 22, 158, 160 academic degrees, 310 acronyms differentiated from, 158 for amino acids, 245t–246 Canadian provinces and territories, 162 capitalization, 146, 150, 156, 159, 227, 228, 272 case sensitivity, 159 chemical reactions, 272, 273 commonly used in chemistry, 169–202 computer and Internet terms, 163–168 deﬁning, 22, 158, 160, 245, 371, 372, 373 devising your own, 158, 169 editorial style overview, 158–162 Abbreviations—continued at editor’s discretion, 158, 169 in equations, 160, 211, 217 in ﬁgures, 225, 365 in foreign names, 153 genus name repetition, 160 in government agency references, 313 isotopic labeling, 265 in mathematical copy, 213, 217 mathematical symbols differentiated from, 160, 211 for monosaccharides, 243t for months, 160–161 not needing deﬁnition, 158–159, 217–218, 260 for nucleic acids, 244t for organic groups, 260 period use, 118, 119, 223, 294 plural forms, 161 for publisher names, 302 reporting analytical data, 274 roman type use, 154–155, 159–160, 212– 213, 216, 271–272 for saccharides, 243t–244 in tables, 160, 225, 370, 371, 372, 373 in titles, 20, 150, 159, 160 U.S. states and territories, 162 for volume information in references, 303–304 See also Acronyms, Chemical Abstracts Service Source Index (CASSI) abbreviations, Symbols, Units of measure Copyright 2006 American Chemical Society 389 390 ➤ The ACS Style Guide Absolute conﬁguration D and L forms, 236, 270–271 R and S forms, 270 Absolute constructions, dangling modiﬁers compared with, 45, 112 “Abstract”, capitalization in references, 303 Abstracts abbreviations deﬁned in, 22, 158, 160 abstract number in references, 298–299 datuments as alternative, 88–89 mathematical symbols deﬁned in, 211 references to meetings and conferences, 307–308, 321 scientiﬁc paper format, 21–22 Abuse, ethical considerations, 74 Academic degrees “a” vs “an” before, 53 abbreviations, 310 in bylines, 21 thesis levels, 309–310 Acceptance of submissions communications (journal presentations), 19 manuscripts, 12, 28 notiﬁcation of, 64 peer-review role, 71 Accepted manuscripts, processing, 33–35 See also Editorial process, Electronic submission of manuscripts Accession dates, Internet sources, 315, 317– 321, 324 Accession numbers, U.S. government publications, 312 Acids, capitalization examples, 237t Acknowledgments ethical obligations, 8, 14 scientiﬁc paper format, 24 Acrobat Distiller (software), 351 Acrobat Reader (software), 60, 68, 351 Acronyms abbreviations differentiated from, 158 in abstracts, 22 commonly used in chemistry, 169–202 computer terms, 156, 163–168 editorial style overview, 158–162 period use, 119 for publisher names, 302, 307 See also Abbreviations, Symbols ACS books author guidelines, 29, 343 column dimensions, 354t copyright policy, 30 ﬁgure costs, 350 reference format, 24, 287–290 template downloads, 29 See also Copyright, Editorial process, Peer review ACS committees, capitalization guidelines, 147 ACS Copyright Learning Module Web site, 82 ACS Copyright Ofﬁce contact information, 79b, 84b Copyright Status Form, 86 requesting permission from, 84b ACS copyright policy, 30, 79b, 82 ACS Copyright Status Form, 86 ACS desk references, 127, 135 ACS governing bodies, capitalization guidelines, 147 ACS journals and magazines ASAP articles, 34 author guidelines, 29, 343, 381b, 382b CASSI abbreviations, 288t column dimensions, 354t copyright policy, 30 ethical guidelines, 11–16 ﬁgure costs, 350 ﬁgure guidelines, 343, 347, 351, 364 hazard footnotes in, 23 home pages, 28b numbers style, 208 parameter settings, 381b reference format, 24, 287–290, 291 reference management programs, 327 structure guidelines, 381b, 382b supporting information availability, 25 table guidelines, 374 template downloads, 29 type size, 356 See also Copyright, Editorial process, Peer review ACS local sections, capitalization guidelines, 147 ACS magazines, See ACS journals and magazines ACS Paragon Plus System, 30, 364, 374, 382b ACS Paragon System electronic submission of manuscripts, 60, 62, 69t submission of artwork, 30, 364, 374, 382b ACS periodicals, See ACS journals and magazines ACS Permission Request Form, 84b ACS permission request guidelines, 83–86 ACS publications ASAP articles, 34, 318–319 author guidelines, 29, 343, 381b, 382b column dimensions, 354t copyright policy, 30 credit lines in, 367b ﬁgure costs, 350 ﬁgure guidelines, 343, 346, 364 numeral and word usage, 206 parameter settings, 381b Index ACS publications—continued reference format, 24, 287–290, 291, 300, 317 template downloads, 29 trademark symbols not used in, 23 type size, 356 See also ACS journals and magazines, Copyright, Editorial process, Peer review ACS Publications Division ASAP articles, 318 copyright owner rights, 78 Copyright Status Form, 86 requesting permission from, 79b, 83, 84b Web site, 86 ACS quotation marks policy, 121–122 ACS spelling preferences, 129–133 Active voice, writing style, 42, 54 Adaptation of artwork, 84b, 366 Addition compounds, centered dot use, 261 Addresses, computer, See Electronic mail (e-mail) addresses, Uniform resource locator, World Wide Web sites Adjectives comma use, 115–116 mathematical operators used as, 219 mathematical symbols used as, 215 phrasal, 149 predicate, 143 proper, 137, 143, 152 trademarks as, 146, 157 as unit modiﬁer element, 139–140, 143 See also Unit modiﬁers Adobe software electronic submission of manuscripts, 61, 68 ﬁgure preparation, 350–352, 355b, 363 Advanced Chemistry Development software, 379–380, 380b “Advances” as CASSI keyword, 306 Adverbs hyphenation guidelines, 141 semicolon use, 119–120 as unit modiﬁer element, 140 “Affect” vs “effect” or “impact”, 52 Afﬁliation company name styling, 162 scientiﬁc paper format, 21 Afﬁrmative sentences vs double negatives, 45 Agents, submitting, 62 Agreement, subject–verb, 43–44, 105–108 Alcohols capitalization examples, 237t forms for, 234b Alicyclic compounds, nomenclature, 236 Alignment chemical structures, 379 columnar material in tables, 370, 372, 373, 374 ➤ 391 Alignment—continued columns containing numbers, 207, 372 superscripts and subscripts (stacking), 269 “All”, subject–verb agreement, 108 “Alpha (α) particle”, capitalization of “p”, 149 “Alpha” vs α, 155 Alphabet, Greek, 214 See also Greek letters Alphabetizing CASSI abbreviations, 294 reference citations, 289 reference lists, 325 unnumbered lists, 374 alt inﬁx in copolymer names, 243 “Although” instead of “while”, 46 “a.m.”, 205 American Institute of Physics, 60, 62, 69t American Library Association, 311 American National Standards Institute (ANSI), 276 American Society for Testing and Materials, 276 Amino acids abbreviations, 245t–246 small capital letter use, 236, 245, 270 “Among” vs “between”, 51 Ampersand in Web addresses, 156 “an” vs “a”, See “a” vs “an” Analytical data reporting, 274–276 as supporting information, 25 See also Data, Physical quantities, SI units, Units of measure “And” vs “and/or”, 56 with author citations in text, 289 as coordinating conjunction, 47, 113, 149 vs en dash, 124–125 number of subject, 106 between numbered items, 209 vs plus sign, 55, 211 slash misused for, 56 vs “with” constructions, 56 “And/or”, 56 “And so forth”, 160 Angle brackets, with crystallographic indices, 268 Angular degree or time symbols, 203, 224 Angular vs linear formulas, 267, 376 Anhydrides, capitalization examples, 237t Animations, Web-enhanced objects, 25 Anions, charged, 266 Anomeric conﬁguration of saccharides, 243 Anonymity of peer reviewers, 8, 71–72 ANSI, See American National Standards Institute 392 ➤ The ACS Style Guide Antecedents of pronouns, 45–46, 58 “Any”, subject–verb agreement, 108 Apostrophes plurals of abbreviations, 161 of decades, 205 of mathematical symbols, 211 of numerals used as names, 206 possessives, 127 Apparatus, “Experimental” section contents, 22 “Appendix”, capitalization, 144 Appendixes in scientiﬁc papers, 24–25 Application ﬁles for artwork deﬁnition, 350 Excel ﬁle tips, 353b PDF ﬁle creation, 351 See also Computer ﬁle formats, speciﬁc applications Appositives, restrictive and nonrestrictive, 116–117 Aqueous state, indicating in reactions, 272 Ar designation for aromatic substituents, 246, 250 Arabic numerals, See Numerals Arabic surnames, 152 Area graphs types of artwork, 347 working with, 363 Arguments (mathematical) deﬁnition, 210 enclosing marks for clarity, 216 spacing considerations, 214, 219 Arial typeface, 357b Aries Systems, editorial systems, 60, 69t Aromatic compounds, 240 Aromatic substituents, 246, 250 Arrays, mathematical concept, 210 Arrows in reactions, 272–273, 379 Article numbering in references, 297 Article reprints, 35 See also Permissions Article titles in periodical citations, 291, 292t Articles (journal), See Journal articles Articles (part of speech) “a” vs “an”, 53, 257, 264 at beginning of titles, 20, 154 capitalization in titles and headings, 149 before collective nouns, 106 before element symbols, 257 in foreign names, 152–153 as gender-neutral alternative, 58 before isotopes, 257, 264 “Articles ASAP” page, 34 Artwork ACS copyright policy, 30 adapted, 84b, 366 Artwork—continued article reprint costs, 35 editorial process, 29–30, 363–365 embedding requirement, 30, 364, 374 handling tips, 362, 364–365 numbering of, 206, 345, 365 permission requirements, 30, 85b, 366 sizing, 352–354, 355, 370, 373 types of, 29, 347–349 See also Charts, Figures, Illustrations, Photographs, Schemes, Structures, Tables “As”, capitalization in titles and headings, 149 “As compared to” and “as compared with”, 50 As Soon As Publishable (ASAP) articles, 34, 318–319 “As well as”, 47 Asian surnames, 152–153 Aspartic acid/asparagine mixtures, 245 Assignment of copyright by ACS, See ACS copyright policy Association of American Publishers, 82 “Assuming” as sentence modiﬁer, 112 “Assure” vs “ensure” or “insure”, 52 Asterisk for corresponding author information, 21 for excited electronic state, 262 for multiplication in computer languages, 211 ASTM International, citing standards, 276 Astronomical terms, capitalization, 149 “at.”, unit of measure, 118 At symbol (@) in e-mail addresses, 157 Atomic numbers left subscript use, 262 list of elements, 258t–259t for unnamed elements, 260 Atomic orbitals, chemical conventions, 256 Atomic substituents or residues, designating, 246, 250–251 Atomic weights, list of elements, 258t–259t Atoms datument validation, 96 electronic conﬁguration, 256–257 isotopic, 265 markup languages and the WWW, 91, 92–94 nuclide descriptors, 261–263 symbols and SI units, 277 Attributes (markup language component), 91–94, 96, 97 Attribution, ethical considerations for, 7 Audience considerations for draft manuscripts, 28b in popular science, 16 word choice, 50 Index Author–date citations multiple references by same author, 290 reference collation, 290, 325 reference format, 30, 287, 289–290 Author guidelines ACS publications, 29, 343, 381b, 382b additions or corrections, 35 CIF format, 286 conventions in chemistry, 255 datument validation, 96 electronic submission of manuscripts, 30, 60, 63 ﬁgure submission, 343, 363–365 numeral and word usage, 206 peer-review process, 75 reference format, 31, 291 references to books, 300 standard format, 20, 25, 26, 28–29 structure submission, 381 table preparation, 370 Author home page, 62, 63, 64, 68 Author names in references books, 300–301 e-mail messages, 322 editorial process overview, 30 organization or committee as author, 301, 307, 308, 312, 321 periodicals, 291, 297–299 reference collation, 290, 325–326 theses, 309 U.S. government publications, 312 Author names in text byline format, 21, 152 citation guidelines, 30, 287, 289–290 period use and spacing, 119 Author responsibility checking proofs, 33–35, 36 datument potential, 98–99 datument validation, 96 ethical considerations, 3–8, 13–15, 16, 27 graphics insertion, 379 paperwork submission, 32, 33 peer-review process, 75–76 reference accuracy, 24, 30, 31, 290 See also Author guidelines, Copyright entries, Permissions Author’s complimentary copy, 35 Author’s proof, 33–35, 36 Authorship copyright considerations, 79, 81, 86 determining, 6–7, 14, 21 order of names as issue, 6 See also Coauthors, Multiple authors Auxiliary verbs, in compound sentences, 108 ➤ 393 Axes crystallographic notation, 268, 269 mathematical use and italic type, 212, 223 orbital, 256 scaling and labeling, 225, 359–360 b inﬁx in copolymer names, 243 Bar graphs color use, 345b examples, 359f types of artwork, 347 when to use, 344 working with, 363 Base pairs, representation of, 244 “Based on” vs “on the basis of ”, 52, 111 Bases, numbering in nucleotide sequences, 244t “Because” instead of “since”, 46 “Because of ” instead of “due to”, 112 Behavioral guidelines, See Ethical guidelines Beilstein references, 299 Bench>Press (software), 60, 62, 69t Berkeley Electronic Press, editorial systems, 60 “Beta (β) particle”, capitalization of “p”, 149 “Beta” vs β, 155 “Between” vs “among”, 51 “Between … and”, 125, 209 “bi” in element names, 260 Bias bias-free language, 57–58 and peer reviews, 9, 15, 75 Bibliographic citations, See Reference entries Bibliographic indexes, foreign surname format, 152 Bibliographies, abbreviation use in, 160 See also Reference entries Biblioscape (software), 326–327 Billions, 204 BinHex ﬁles, 62 Binomial terms, See Taxonomic terms Bio-Rad software, 379–380, 380b Biochemistry, reference format exceptions, 291, 300, 301 Biological structure data sources, 284 Biological test data as supporting information, 25 “Bis” as multiplying preﬁx, 235 Black-and-white (B&W) mode, 350, 351, 352t, 362 Blackboard boldface letters, 214 blend inﬁx in copolymer names, 243 block inﬁx in copolymer names, 243 BMP format, 381 Boiling points, reporting analytical data, 274 Boldface type with CASSI abbreviations, 295 chemical name numbering, 206 394 ➤ The ACS Style Guide Boldface type—continued chemical structure identiﬁcation, 274, 376–377 combinatorial chemistry representation, 246 for Greek letters, 214 in mathematical copy, 213 references to periodicals, 296 superatom representation, 246 Bonding orbitals, chemical conventions, 256 Bonds punctuation, 244, 267 symbols, 243, 244 Book as reference author names, 300–301 book title and editions, 301–302, 306 books with editors, 292t, 300–301, 320 books without editors, 292t, 300, 319–320 chapter title, 301, 306 computer program citation format, 323–324 editor names, 300–302, 320 examples, 292t–293t meetings and conferences, 307–308 miscellaneous information, 305 online books, 293t, 314, 319–320 organization or committee as author, 300, 307 pagination information, 304 place of publication, 303 publisher name, 302–303 series publications, 292t, 304, 305–306 special situations, 305–306 volume information, 303–304, 306 year of publication, 303 See also References Book titles in book citations, 301–302, 306 italic type for, 154 in presentation citations, 307–308 U.S. government publications, 312 Books (in general) artwork sizing, 354, 370, 373 table footnotes, 373 types of, 17–18 word choice, 50 See also ACS books, Manuscript entries, Scientiﬁc papers Borrowed material, See Adaptation of artwork, Copyright, Permissions “Both”, subject–verb agreement, 108 “Both … and”, 47 Boughton system, isotopic naming, 265–266 Braces with crystallographic indices, 268 in mathematical copy, 212, 214, 216 in mathematical equations, 219–220 Braces—continued nesting order, 216 in set notation, 222 with syllabic portion of chemical names, 240 Brackets, See Angle brackets, Curly brackets, Square brackets Bragg reﬂection, crystallography, 267 Branched residues of saccharides, 244 Brand names editorial style, 157 scientiﬁc paper format, 23 in titles, 20 See also Trademarks Bravais lattices, 269 Breaks at end of line, See Line breaks Bridged compounds, nomenclature, 236 Browsers, See Web browsers Bulletins, technical, 292t, 314, 324 Bureau International des Poids et Mesures, 255 “But” as coordinating conjunction, 113 parallel construction, 47, 48 in titles and headings, 149 B&W mode, 350, 351, 352, 362 Bylines foreign surname format, 152 scientiﬁc paper format, 21 See also Authorship Cadmus Systems, editorial systems, 60, 62, 69t Callouts, See Citations in text Cambridge Crystallographic Data Centre, 284, 286 Cambridge Structural Database, 284 Cambridgesoft software, 350–351, 379–380, 380b, 381b, 382b Camera-ready artwork deﬁnition, 343 preparation guidelines, 346 submission guidelines, 364–365 See also Hard copy Canada, province and territory abbreviations, 162 Canadian Domestic and Non-Domestic Substance Lists, 254 Canonical building blocks of nucleic acids, 244 Capitalization abbreviations, 146, 150, 156, 159, 227, 228, 272 amino acid abbreviations, 245 axis labels on ﬁgures, 360 case-sensitive abbreviations and symbols, 159 chemical element symbols, 145, 240–241, 257 chemical names, 143, 145, 151, 233, 235– 241, 237t–239t Index Capitalization—continued chemical reaction types, 273 after colons, 120, 144 company and organizational names, 147 computer and Internet terms, 156, 163–168 computer languages, 155 computer protocols, 156 computer software, 156 event names, 148 “ﬁgure”, “table”, “chart”, and “scheme”, 143, 345, 369 parenthetical sentences, 123 parts of a book, 144 planet names, 149 polymer names, 146, 150, 237t, 242–243 professional titles, 147 references to periodicals, 291, 299 regions of the country, 148 SI units, 228 small capital letters, 233, 236, 238t, 245, 270–271 spelling recommendations list, 129–133 surnames, 151–152, 153, 225 taxonomic names, 145–146, 150 in text, 143–148 in titles and headings, 148–151, 227, 237t–239t trademarks, 147, 157 units of measure, 150, 225, 227 words preceded by element symbols, 145 Captions abbreviation use, 160 colon use, 120 as copyright ownership indicator, 81 manuscript submission, 364 parallelism, 48 preparing, 355, 365 sizing artwork, 354 symbol keys, 365 Carbohydrates, small capital letter use, 236, 270 Cardinal numbers, 203–204, 308 See also Numbers CAS, See Chemical Abstracts Service Cascading Style Sheets (CSS), 90 Case sensitivity for abbreviations, 159 Cases regarding copyright, 80, 82 CASSI, See Chemical Abstracts Service Source Index Catalysts, indicating in reactions, 272 Cations, charged, 266 “Caution:”, “Experimental” section contents, 23 CD-ROM publications cited as references, 293t, 322–323 illustration preparation, 346 Celsius, capitalization, 225 ➤ 395 Centered dot for bond formation or breaking, 267 in chemical formulas, 260 with compound units of measure, 224 in mathematics, 215, 219 nucleic acid representation, 244 spacing guidelines, 215, 219, 261 Centering of text and artwork, See Alignment CG Information software, 327 CGS system, background of, 228 “Chapter”, capitalization, 144, 303 Chapter number in book references, 303 Chapter titles in book references, 301, 306 in U.S. government publications, 312 Charges electric, 256 ionic, 262, 266 “Chart”, capitalization, 143 Charts citing, 143 editorial process, 29 groups of structures as, 376, 377, 379 numbering, 206, 377 permissions, 83 titles, 148 types of artwork, 347 when to use, 344 working with, 363 See also Artwork Check-CIF utility, 63, 286 Checking proofs, 33–35, 36 Chemaxon software, 380, 380b ChemDraw (software), 350–351, 379–380, 380b, 381b, 382b Chemical Abstracts (CA) Boughton system for isotopes, 265 and CAS Registry Numbers, 253, 254 citing references in text, 298–299 datuments as alternative, 89 patent citation format, 310 Chemical Abstracts Service (CAS) chemical nomenclature, 233 Chemical Registry System, 91, 94, 253–254 Chemical Abstracts Service Source Index (CASSI) computer program citations, 324 meeting and conference presentation citations, 308 publisher names and addresses, 302 sample entry, 340–341 series publications, 306 Chemical Abstracts Service Source Index (CASSI) abbreviations of ACS periodicals, 288t commonly cited journals list, 328–339 government agency references, 313 396 ➤ The ACS Style Guide Chemical Abstracts Service Source Index (CASSI) abbreviations—continued sample entry, 340–341 series titles, 306 use guidelines, 291, 292–293 Chemical apparatus, describing, 22 Chemical descriptors capitalization, 145, 238t–239t, 240 style guidelines, 234–236, 240, 241, 270–271 in titles and headings, 150 types of, 233 See also Stereochemical descriptors Chemical elements chemical conventions, 257–261, 264 crystallographic indices, 268 isotopes, 263–266 list, 258t–259t nuclide descriptors, 262–263 unnamed, 260 See also Element symbols Chemical formulas bonds, 267 Chemical Abstracts index of, 254 chemical conventions, 257–261 concentrations, 271 “Experimental” section contents, 22, 23 isotopic nuclides, 264 linear vs angular forms, 267, 376 nuclide descriptors, 262–263 preﬁx treatment, 235 roman numerals in, 262 in titles, 20 Chemical inventories, commercial, 254 Chemical kinetics, symbols and SI units, 277–278 Chemical literature, popular, 16 Chemical markup language, See CML Chemical names boldface numbering sequence, 206 capitalization, 143, 145, 151, 233, 235–241, 237t–239t CAS Registry Numbers, 253–254 components of, 233–240 “Experimental” section contents, 22 hyphenation at end of line, 233, 241, 247–249 hyphenation of preﬁxes and sufﬁxes, 138, 235–236, 270 isotopic labeling, 264–266 locant and descriptor portion of, 234–240, 238t–239t multiword examples, 237t numeral and word usage, 206 punctuation in, 241 specialized groups of chemicals, 242–246 syllabic portion of, 233, 240, 241 Chemical names—continued as unit modiﬁers, 141, 143 See also Chemical descriptors, Chemical nomenclature, Locants Chemical nomenclature authoritative sources, 233 and CAS Registry Numbers, 254 published updates, 255 punctuation, 124 roman type use, 212 systematic vs trivial, 22 See also Chemical names Chemical purity, degree of and criteria for, 22 Chemical reactions abbreviation use, 272, 273 arrows in, 272–273, 379 concentrations in, 271 displayed vs run in, 272, 376 grouped as schemes, 376, 377f numbering, 272, 377 preparing, 378–381 spacing guidelines, 272, 379 submitting, 381–382 See also Schemes Chemical Registry System, CAS, 253–254 Chemical research, ethical guidelines, 11–16 Chemical safety information in abstracts, 21 ethical guidelines, 13 “Experimental” section contents, 23 Chemical structures, See Structures Chemical symbols case sensitivity, 159 element names used with, 260 list, 169–202, 258t–259t published updates, 255 roman type use, 212, 259 See also Abbreviations, Element symbols, SI units, Symbols, Units of measure, speciﬁc symbols Chemical terms capitalization, 143 datument vocabularies, 97 Greek letter use, 155 hyphenation of preﬁxes, 137 See also Chemical descriptors, Chemical names, Chemical nomenclature Cheminnovation (software), 379–380, 380b Chemistry 4-D Draw (software), 379–380, 380b ChemSet notation, 246, 251–252 ChemSketch (software), 379–380, 380b ChemWindow (software), 379–380, 380b Child elements (markup language component), 91, 93 Chime (plug-in), 25 Index Chinese surnames, 152 Chirality, 270–271 CIF, See Crystallographic information ﬁles Circling of charges, 262 Circuit diagrams as supporting information, 25 “Cis”, italicization and capitalization, 145 Citation manager programs, 326–327 Citations in text in abstracts, 22 of equations, 221 of ﬁgures, 143, 345–346 of footnotes, 373 of numbered items, 209 of structures and schemes, 143, 376–378 of tables, 143, 369–370 See also Reference entries City and state names for place of publication, 294, 295, 303, 310, 328 Class names (taxonomic), capitalization, 145–146 Classroom use of copyrighted materials, 80 Clause, deﬁnition, 42 CML (chemical markup language) datument validation, 96–97 display of, 94, 96 examples of, 92–94, 93s structure submission, 382 CMYK color mode, 350, 352, 362 “Co.”, 162, 303 co inﬁx in copolymer names, 243 “Co-workers” in textual citations, 289 Coauthors ethical obligations, 14 reference citation wording, 289 See also Authorship, Multiple authors Code of Federal Regulations, cited as reference, 313 CODEN abbreviation, 340 Collating references, 290, 325–326 “Colleagues” in textual citations, 289 Collective nouns, 106–107 Colon capitalization after, 120, 144 with display equations, 221 in ﬁgure captions, 120 general use, 120 misuse with components of mixture, 121, 261 in ratios, 121, 215, 222 references to U.S. government publications, 312 between verb or preposition and object, 121 Color artwork, and reprint costs, 35 Color combinations, hyphen use, 125, 140 Color modes, 350–352, 362 Color photographs, 362 ➤ 397 Color use in ﬁgures, 344, 345b, 346, 350, 353b Column number in references, 298 Column widths for ACS publications, 354t Columns in tables, See Tables Combinatorial chemistry, representation of, 246, 250–252 Combinatorial libraries, 246, 250–252 Combos (artwork) deﬁnition, 347 example, 349f ﬁle formats, 352t working with, 347, 363 Comma between adjectives, 115–116 with appositives, 116–117 in chemical names, 241 with compound predicates, 115 with coordinating conjunctions, 113, 114, 115 with dates, 118 and display equations, 221 with “et al.”, 117–118, 289 with geographical locations, 118 with introductory words and phrases, 48, 114 with “Jr.” and “Sr.”, 117 between modiﬁer and subject, 110 with nonrestrictive clauses, 44, 109, 116 in numbers with ﬁve or more digits, 207–208 in numbers with four digits, 207 with quotations, 118 reference citation guidelines, 289–290 with reference citation numbers, 117, 209, 289 references to books, 301–302 references to meetings and conferences, 308–309 references to periodicals, 296–299 references to U.S. government publications, 312–313 serial, 114, 115, 119 with subordinate clauses, 114 with subordinating conjunctions, 116 with two or more adjectives, 115–116 with units of measure in tables, 371 verb separated from subject, object, or predicate noun by, 114–115 Commercial chemical inventories of regulatory agencies, 254 Committee on Nomenclature, Terminology, and Symbols of the American Chemical Society, 233 Committees as authors, 301, 307 Communications (journal presentation type), 18–19 See also Personal communications 398 ➤ The ACS Style Guide Companion publications, cited as reference, 299 “Company”, when to abbreviate and when to spell out, 162 Company logos, copyright basics, 83 Company names capitalization, 147 MSDS citation, 315 parentheses use, 22, 124 spelling and styling, 127 in titles, 20 when to use, 162 Comparatives, hyphenation in unit modiﬁers, 141 “Compared to” vs “compared with”, 48, 50 Comparisons sentence structure, 48–50 word choice, 50–51 Complementary base pairs, representation, 244 Complex sentences, deﬁnition, 42 Complimentary copies, 35 Components of mixtures, punctuation, 121, 126, 222, 261 Components of vectors and tensors italic type use, 212 as mathematical concept, 210 “Composed of ” vs “comprised”, 53 Compound predicates, 115 Compound sentences, deﬁnition, 42 Compound subjects, 106–107 Compound surnames, hyphenation, 139, 152–153 Compound units of measure, 224, 226, 230t Compound words capitalization, 150 deﬁnition, 138 hyphenation, 138–139 See also Phrasal verbs, Unit modiﬁers Compression of computer ﬁles, 62, 351 “Comprised” vs “composed of ”, 53 Computer addresses, See Electronic mail (e-mail) addresses, Uniform resource locator, World Wide Web sites Computer databases, See Databases Computer disks for ﬁgure ﬁles, 364 Computer ﬁle formats application ﬁle deﬁnition, 350 compressed ﬁles, 62 crystallographic information ﬁles, 25, 63, 97–98, 270, 284–286 datument potential, 98 e-mailed ﬁles, 61–62 electronic submission of manuscripts, 59–63, 68, 69t ﬁgure preparation, 346, 350–353b, 357b, 361, 363 manuscript templates, 20, 29, 60 Computer ﬁle formats—continued reference management programs, 326 structure preparation, 381 word-processing vs PDF ﬁles, 60–61 Computer languages asterisk use, 211 capitalization, 155 Computer monitors ﬁgure preparation issues, 346, 347, 350, 352 font tips, 357b Computer platforms PDF ﬁle portability, 61 reference manager programs for, 327 templates for, 29 Computer programs, See Software programs Computer protocols, capitalization, 156 Computer software, See Software programs Computer terminology list, 163–168 Computerized title searches, 20 Concentrations conventions in chemistry, 271–272 square brackets use, 124, 271 “Conclusions” section in scientiﬁc papers, 7, 23 Conduct guidelines, See Ethical guidelines Conference proceedings description, 17 reference format, 292t, 307–309, 321, 323 standard reporting format, 19 Conﬁdentiality of submitted manuscripts, 9, 12, 15, 16, 73–74 Conﬁgurational preﬁxes, chemical names, 235, 241, 243, 245, 270–271 Conﬂicts of interest author responsibility to reveal, 8, 12, 15 in editorial process, 12–13 in review process, 9, 15, 75 Confusable words and phrases, 51–53, 111–112 Conjunctions, See Coordinating conjunctions, Correlative conjunctions, Subordinating conjunctions Conjunctive adverbs, semicolon use, 119–120 Conseil Européen pour la Recherche Nucléaire (CERN), 89 Constants deﬁning symbols in text, 211 Greek letter use, 214 italic type use, 212 mathematical abbreviations and symbols, 211, 217–218 as mathematical concept, 210 roman type use, 213 Contents page, hazard footnotes on, 23 Context of research, ethical considerations, 7–9 Continuous-tone art, See Halftone art Contractions, avoiding, 55 Index Contracts and copyright, 78, 82 Controlled vocabularies, 97–98 Conventions in chemistry atoms and molecules, 261–266 bonds, 267 chemical elements and formulas, 257–261 chemical reactions, 272–274 chirality, 270–271 concentration, 271–272 crystallography, 267–270, 284–286 electronic conﬁguration, 256–257 periodic table, 261 physical quantity symbols, 277–283 radicals, 266 reporting analytical data, 274–276 subatomic particles and quanta, 256 Coordinating conjunctions capitalization in titles and headings, 149 comma use, 113, 114, 115 deﬁnition, 47 number of subject, 106 parallelism, 46, 47, 48 Coordination compounds capitalization examples, 237t square brackets use, 260 Coordination numbers, 270 Copolymer names, 243 Copy editors (in general) proofreaders’ marks, 36–39 role, 33 See also Editorial process, Editors Copyright basic rights, 79 copyright notice, 79–80, 83 duration of, 81, 82 electronic media, 81, 82, 83 excerpts, 80 fair use, 80–81 font software, 357b, 363 materials not protected by, 78 materials protected by, 77–78, 81–82 misconceptions about, 81–82 ownership, 78, 81–82, 83, 84b, 86 permission request guidelines, 83–86, 366 photographs, 81–82, 361, 366 public domain status, 81, 83 registration, 79–80 reproduced artwork, 29, 83–86, 366 transferring, 32, 33, 78, 82, 86 U.S. government works, 81, 366 U.S. law, 77–82 works made for hire, 78, 82 See also Permissions Copyright infringement, 80, 82, 357b Copyright laws, 77–82 Copyright notice, 79–80, 83 ➤ 399 Copyright policy, ACS publications, 30, 79b, 82 Copyright registration, 80 Copyright Status Form, ACS, 86 Copyright transfer, 32, 33, 78, 82, 86 Corel Draw (software), 351 “Corporation”, when to abbreviate and when to spell out, 162 Corrections to draft manuscripts, 36 to proofs, 34, 36 to published manuscripts, 35 See also Errors entries Correlative conjunctions deﬁnition, 47 parallelism, 46, 47 Correlative constructions, for parallelism, 46, 47 Correspondence (journal presentation type), 18 Corresponding author author home page, 62, 63 contact information, 21 role in editorial process, 33, 34 Country names for place of publication, 294, 295, 303, 310 Court cases on copyright, 80, 82 Cover letters for manuscripts, 32, 76 Credit lines ﬁgure captions, 366, 367b for previously published material, 84b, 85b, 86, 366, 367b Critical review of manuscripts, See Peer review Criticism, in scientiﬁc writing, 7–8, 14, 16, 74 Cropping of photographs, 352, 360, 362 cross inﬁx in copolymer names, 243 CrossRef application, 317 Crystallographic information ﬁles (CIF) basic principles, 284–285 and datument vocabularies, 97–98 editors for, 286 electronic submission of manuscripts, 63 journal submission requirements, 285–286 as supporting information, 25 validation reports, 63, 286 WWW resources, 284, 286 Crystallography CIF format, 25, 63, 97–98, 270, 284–286 crystallographic point groups, 269 lattice types, 269 planes and directions in crystals, 267–268 space groups, 269–270 symmetry operations and structural point groups, 269 CRYSTMET database, 284 CSS (cascading style sheets), 90 Cultivar names, capitalization, 145–146 Curly brackets, combinatorial chemistry representation, 246, 251–252 400 ➤ The ACS Style Guide Curves, plotting in ﬁgures, 358–359 Cyan–magenta–yellow–black (CMYK) color mode, 350, 352, 362 “cyclo” preﬁx, style for, 236 D in chemical names, 236, 245, 270–271 dA•dT and dG•dC pairings, 244 Dangling modiﬁers, 45, 109–113 Dashed lines for ﬁgures, 345f, 358 for structures, 378 Dashes, See Em dash, En dash Data (in general) CIF format requirements, 284–286 CIF terminology, 284–285 embedding in Excel ﬁles, 353b ethical considerations in presentation, 5 reporting analytical data, 274–276 as source of original ﬁgure or table, 84b, 366 as supporting information, 25 and types of artwork, 344, 369 See also Databases, Datuments “Data” as singular or plural noun, 106 Data entry numbers, reference format, 314, 320, 324 Data sets, reference format, 314–315 Databases CAS Chemical Registry System, 253–254 crystal structure data sources, 284 data set citation, 314 datuments as alternative, 89 disclosure of research results via, 16 reference collation and management, 326 reference format, 293t, 318, 320, 324 XML display example, 94, 96 Date of access for Internet reference citations, 315, 317–321, 324 Dates comma use, 118 month abbreviations, 160–161 numeral and word usage, 160, 205 See also Year of publication Datuments authoring and editing tools, 98–99 cost-saving potential, 99 documents compared with, 87–89, 96 identiﬁer use, 94 markup language display, 94–96 markup language examples, 90–94 markup languages and the WWW, 89–90 as scientiﬁc grid component, 99–100 subsets, 94 validation, 96–97 vocabularies, 97–98 “D.C.”, CASSI spacing exception, 294 Deadline concerns, See Timeliness as issue Decades, numerals and plural forms, 205 Deceased authors, acknowledgment of, 14 Decimals and decimal point use, 208, 372 Declarative sentences period use, 118 writing style, 41–42 Deﬁnitions used by markup languages, 93, 97–98 Degree of accuracy, numbers style, 208–209 Degree of rotation, crystallographic point groups, 269 Degree symbol decimals use, 208 not used with kelvin, 227 spacing, 203, 224 Degrees, academic, See Academic degrees “Delta (∆)”, spelling out, 155 Demonstrations, citation guidelines, 307, 321 Deoxyribonucleic acid, abbreviations, 244t Dependent clauses, See Subordinate clauses Derivations, mathematical, 23, 25 Derivative works and copyright, 78 Descriptors, See Chemical descriptors, Nuclide descriptors, Stereochemical descriptors Designation digits for superatoms, 246, 250–251 Determinants italic type for elements, 212 as mathematical concept, 211 roman type for determinants, 213 Deuterium, representation, 264, 266 Dictionaries ACS desk references, 127, 135 as CIF component, 97–98, 284 as markup language component, 93, 97 “Different from” in comparisons, 49 Digital Object Identiﬁer (DOI) system, 317, 319 Digital photographs, 360, 361f See also Photographs Digits, See Numerals Dimensions of ACS publications, 354t Directions in crystals, 267–268 “Discussion” section in scientiﬁc papers, 7, 23 Disks for ﬁgure ﬁles, 364 Display equations in abstracts, 22 numbering of, 220 punctuation before and after, 221 style and usage guidelines, 211, 218 See also Equations Displayed chemical reactions, See Chemical reactions Dissertations, cited as reference, 292t, 309– 310, 321, 325 Distiller (software), 351 Index Ditto marks in tables, 372 Division, slash or negative exponent use, 220, 224 DNA, abbreviations, 244t Document root elements (markup language component), 91 Document titles, U.S. government publications, 312 DOI (Digital Object Identiﬁer) system, 317, 319 Dollar sign, spacing, 203 Dot, centered, See Centered dot Dot, superscript, 266 Dot-matrix printers avoiding for artwork, 353b, 360 TrueType font format, 357b Dot size and spacing in halftone art, 347 Dots per inch (dpi), in ﬁgure preparation, 346 Dotted lines in ﬁgures, 358 Double-blind peer reviews, 71 Double bonds in chemical formulas, 267 Double negatives, avoiding, 45 Double surnames, hyphenation, 139, 152–153 Doubled letters, hyphenation rules, 136 Draft manuscripts, processing of, 27–31 See also Editorial process, Electronic submission of manuscripts Drawing programs, 350–352, 363, 378–383 Drawing settings for ACS publications, 381b Drawings, 347 See also Artwork, Figures, Illustrations, Structures DrawIt (software), 379–380, 380b Drug names capitalization, 145 in titles, 20 Dublin Core Schema, 90 “Due to”, 51, 111–112 DVDs, cited as references, 293t, 322–323 e (base of natural logarithm) “exp” vs e, 217 roman type use, 213 “e” for negative electron, 256 “e” or “E” in scientiﬁc notation, 210 E preﬁx in chemical names, 236 “Each”, subject–verb agreement, 107 “Earth”, capitalization, 148 “Ed.” vs “ed.”, 301, 302 EdiKit (software), 60 Editable fonts, description, 357b Editing services, 75 Edition numbers for books, 301 Editor names in references, 292t, 293t, 300– 302, 320 Editorial computer systems, See Electronic submission of manuscripts ➤ 401 Editorial lists, See Lists, editorial Editorial Manager (software), 60, 62, 69t Editorial process accepted manuscripts, 33–35 CIF format and text editors, 286 datument potential, 98–99 draft manuscripts, 27–31 editing services, 75 electronic submissions process, 31, 32, 59–69 ﬁgure submissions, 343, 346–347, 363–365 ﬁnal manuscripts, 32–33 proofreaders’ marks, 36–39 reference management programs, 326 review of manuscripts, 31 structure submissions, 381–382 table submissions, 374 Editorial style, See speciﬁc aspects, e.g., Capitalization Editors (in general) CIF validation reports, 286 ethical guidelines, 12–13 proofreaders’ marks, 36–39 role, 33 See also Editorial process Educational use of copyrighted materials, 80 “Effect” vs “affect” or “impact”, 52 “e.g.”, 117, 160 “Either”, subject–verb agreement, 107 “Either … or”, 47 eJournal Press, editorial systems, 60, 69t EJPress (software), 60, 62, 69t Electric charges, indicating, 256 Electricity and magnetism, symbols and SI units, 278–279 Electrochemistry, symbols and SI units, 279 Electron charges, indicating, 256 Electron shells and subshells, chemical conventions, 256 Electronic bulletin boards, 16 Electronic ﬁle formats, See Computer ﬁle formats Electronic lists and newsgroups, 293t, 322 Electronic mail (e-mail) manuscript submission via, 31, 59, 61–64 messages cited as references, 293t, 316, 322 permission requests via, 84b word usage, 50 Electronic mail (e-mail) addresses for author home pages, 62 for corresponding author, 21 format of, 157 line break guidelines, 157 word choice, 50 Electronic media, See Internet, Web entries, World Wide Web sites 402 ➤ The ACS Style Guide Electronic reprints, 35 Electronic source citation CD-ROMs and DVDs, 293t, 322–323 computer programs, 314, 323–325 data sets, 314 e-mail messages, 293t, 316, 322 examples, 292t–293t Internet sources, 292t–293t, 314, 316–322 lists and newsgroups, 293t, 322 online books, 293t, 314, 319–320 online periodicals, 292t, 297, 298, 317–319 Web sites, 293t, 314, 320–321 Electronic submission of manuscripts acceptance of manuscripts, 64 advantages of, 59 author home page, 62, 63, 64, 68 CIF format issues, 63, 284–286 editorial process overview, 30, 31, 32 format and procedural issues, 61–62 preparation of ﬁgures, 343, 346–347, 360, 363–365 preparation of materials, 60–61 preparation of structures, 382b revision of manuscripts, 63–64 software and URLS for selected systems, 60, 65t–67t submission process, 63 text and image formats for selected systems, 61, 68, 69t tracking of manuscripts, 62, 63, 64 Element symbols capitalization, 145, 240–241, 257 concentrations, 271 crystallographic indices, 268 isotope speciﬁcation, 263–266 in locants and descriptors, 233, 234, 238t, 240 nuclide descriptor speciﬁcation, 261–263 oxidation number spacing, 262–263 roman type use, 159, 234, 241 spectroscopy data reporting, 276 See also Symbols Elements, chemical, See Chemical elements Elements (markup language component), 91–94, 96–97 Elements of determinants and matrices italic type use, 212 as mathematical concept, 210 Ellipses in mathematical equations, 219 within quotations, 126 with series items, 127 Elliptical clauses as sentence modiﬁers, 113 Elsevier software, 379–380, 380b, 381 Em dash with CASSI abbreviations, 295 for clarity, 126 Em dash—continued with nonrestrictive clauses, 126 in tables, 372 Embedding artwork in text, 30, 364, 374 data in Excel ﬁles, 353b font software in ﬁles, 357b, 363 En dash for bonds, 267 between components of mixture, 121, 126, 222, 261 in multiword concepts, 124–125 in phrases used as unit modiﬁers, 143 with range of three or more items, 117, 125, 209, 289 with reference citation numbers, 117, 209, 289 with surnames, 125, 139 Encapsulated PostScript format, See EPS format enCIFer program, 286 Enclosing marks in mathematical copy, 212, 214–216, 217 in mathematical equations, 219–220 nesting order, 216 with ranges in scientiﬁc notation, 209 roman type use, 212 in set notation, 222 with syllabic portion of chemical names, 240 with units of measure in tables, 371 See also Angle brackets, Braces, Parentheses, Square brackets Encyclopedias, citation guidelines, 293t, 305–306, 320 End-of-line breaks, See Line breaks End-of-line hyphenation, chemical names, 233, 241, 247–249 End-of-line punctuation, display equations, 221 EndNote (software), 326–327 Energy levels, indicating, 256 English units system, background of, 228 “enn” in element names, 260 “Ensure” vs “assure” or “insure”, 52 Enumerated lists, 123, 206–207 Enzymes, 155 Eponyms, capitalization, 144 EPRESS (software), 60 EPS format, 61, 351–352, 357b, 363 “eq” or “eqs”, 221 “Equals” vs equal sign, 211 Equations abbreviation use, 160, 211, 217 in abstracts, 22 citing in text, 221 concentrations in, 271 Index Equations—continued deﬁnition of variables following, 225 displayed, 22, 211, 218, 220, 221 “Experimental” section contents, 23 identiﬁer use and placement, 220 letters for sequencing, 220 numbering, 206, 220, 272, 377 as part of sentence, 221 running into text, 220 spacing guidelines, 219 See also Structures Equilibrium reactions, arrows for, 272 Equipment capitalization of names, 147 identiﬁcation in text, 22, 23 Errata, publication of, 8, 35 Error analysis, 6 Errors corrections, 34–35, 36 in manuscript submission, 60 by printers, 34 in references, 24, 30, 31 in research author obligations, 3–4, 6, 8 editor obligations, 13 peer-review purpose, 72 reader obligations, 9–10 “Erythro”, italicization and capitalization, 145 ESPERE (software), 60 Esters, capitalization examples, 237t “et al.”, 117–118, 289, 291, 312 Eta (η) in chemical names, 235 “etc.”, 160 Ethers, capitalization examples, 237t Ethical guidelines authors, 16 editors, 12–13 purpose of, 11–12 reviewers, 15–16 scientists publishing in popular literature, 16 Ethics in scientiﬁc publication attribution and context concerns, 7–8 author obligations, 3–8, 13–15, 16, 27 authorship determination, 6–7 editor obligations, 12–13 full disclosure of results, 5–6, 8 reader obligations, 9–10 reviewer obligations, 8–9, 15–16, 73, 74, 76 signiﬁcance and timeliness concerns, 4–5 when to publish, 4–6 European Inventory of Existing Commercial Chemical Substances, 254 Event names, capitalization, 148 “Ever”, hyphenation in unit modiﬁers, 141 “Every”, subject–verb agreement, 107–108 Excel (software), 61, 352, 353b ➤ 403 Excerpts, See Extracts (textual) Excited electronic states, 262 Exclusive rights, copyright ownership, 78 “exp” vs “e”, 217 Experimental details in scientiﬁc papers, 22–23, 25 in tables, 373 Exponents “exp” vs “e”, 217 negative, for division, 224 scientiﬁc notation, 210 after subscripts, 216 Extensible markup language, See XML Extensible stylesheet language, 90 Extracts (textual) copyright basics, 80, 83–86 indentation and punctuation, 122 See also Quotations Extraneous words and phrases in article titles, 20 examples, 54–55 “f ” and “ff ” in pagination, 297, 304 Fabrication or falsiﬁcation of data, 4, 10 Faces, crystallographic notation, 267–269 Fahrenheit, capitalization, 225 Fair use, interpretation, 80–81 Family names (personal), See Surnames Family names (taxonomic), capitalization, 145–146 Fax, permission requests via, 84b Federal government publications, See U.S. government publications Federal Register, cited as reference, 313 Fences, See Enclosing marks “Few”, subject–verb agreement, 108 “Fewer” vs “less”, 51 Fictitious names, not to be listed as authors, 14 “Figure”, capitalization, 143, 345 Figure captions, See Captions Figures abbreviation use, 225, 365 abstract guidelines, 22 ACS copyright policy, 30 adapted, 84b, 366 citing, 143, 345–346 color use, 344, 345b, 346, 350, 353b combos, 347, 349f, 352t, 363 credit lines, 366, 367b data set references, 314 deﬁnition, 344 editorial process, 29–30, 363–365 electronic ﬁle formats, 350–352 electronic submission of manuscripts, 61 “Experimental” section contents, 23 grayscale line art, 347, 349f, 352, 363 404 ➤ The ACS Style Guide Figures—continued halftone art, 347, 348f, 360–362, 363 labeling for editorial processing, 364 line art, 347, 348f, 349f, 352, 354–360, 363 vs lists, 374 numbering, 206, 345, 365 permission requirements, 30, 83–86, 366 photograph reproduction, 360–362, 363 preparing, 343, 346–354, 360 problems to avoid, 358f, 359f, 361f publication costs, 344 publication medium, 346, 351–352 references in, 289 scanning tips, 353b, 354, 355b, 360, 362 sizing, 352–354, 355 submitting, 343, 346–347, 363–365 as supporting information, 25 symbol use, 353b, 356, 358f, 363, 365 type sizes and fonts, 353b, 356b, 357b, 358f, 360, 363, 365 types of artwork, 29, 347–349 Web-enhanced objects, 25–26 when to use, 344, 370 See also Artwork, Captions, Illustrations, Photographs, Structures File formats, See Computer ﬁle formats File names for ﬁgure ﬁles, 364 File transfer protocol sites cited as reference, 320 electronic submission of manuscripts, 61–64 Filters, reference manager programs, 326–327 Final manuscripts, processing of, 32–33 See also Editorial process, Electronic submission of manuscripts Financial aid, “Acknowledgments” section contents, 24 Firefox Web browser, markup language display, 94 First person as gender-neutral alternative, 58 writing style, 43–44 Five-digit numbers, 207–208 5′ to 3′ direction for nucleotide sequences, 244 FIZ Karlsruhe, ICSD database, 284 Flow charts, 347 “fold” as sufﬁx, 138, 205 Fontisworks (software), 60 Fonts copyrights, 357b, 363 in ﬁgures, 356b, 357b, 358f, 363, 365 in structures, 380 for symbols, 365 Footnotes abbreviation use in, 160 for charts and schemes, 377, 378 Footnotes—continued for contributor information, 14 for corresponding author information, 21 for hazard indication, 23 for references, 24, 152 in tables, 371, 372–373 “For” as coordinating conjunction, 47, 113 “For example”, 117, 160 Foreign-language journals, cited as reference, 299 Foreign (non-U.S.) patents, 208, 310–311 Foreign phrases as unit modiﬁers, 139 Foreign surnames, 139, 152–153 Formal names, foreign, 152–153 Formal tables deﬁnition, 370 submitting, 374 See also Tables Formats computer ﬁles, See Computer ﬁle formats scientiﬁc papers, See Standard format for scientiﬁc papers Formulas, See Chemical formulas Four-color format, 350 Four-digit numbers, 207 Fractions vs decimals, 208 hyphenation, 139 numeral and word usage, 205 spacing when built-up, 219 subject–verb agreement, 108 in subscripts and superscripts, 217 Fragmentation of research reports, avoiding, 13–14 Fraud, ethical considerations, 74 Free radicals, 266 Free style format for computer program citation, 324–325 Freehand (software), 351–352, 363 Freeware drawing programs, 379–381 “From … to”, 125, 209 FTP sites cited as reference, 320 electronic submission of manuscripts, 61–64 Full disclosure of research results, 5–6, 8 Full papers, See Journal articles Functions italic type use, 212 as mathematical concept, 210 spacing considerations, 214–215, 219 G for general labeling, 265 g inﬁx in copolymer names, 243 Galleys, marking of, See Proofreaders’ marks and sample markups “Gamma (γ) ray”, capitalization of “r”, 149 Index “Gamma” vs γ, 155 Gas state, indicating in reactions, 272 Gender-neutral language, 57–58 General chemistry, symbols and SI units, 279–280 Generic names, 23, 157 Generic structures, in combinatorial chemistry, 246, 250–251 Genotypes, italic type use, 154 Genus names abbreviating vs spelling out, 160 capitalization, 145–146, 150 italic type use, 154 Geographical locations capitalization, 148 comma use, 118 postal abbreviations, 161–162 See also Place of publication Geometric lines and points, roman type use, 213, 223 Geometric planes, italic type use, 212, 223 GIF format, 351–352, 357b, 361, 381 Giorgi system, background of, 228 Given names byline format, 21 foreign name format, 152 hyphenation, 139 See also Author names in references, Author names in text, Initials, Personal names Glutamic acid/glutamine mixtures, 245 “Gold book” (IUPAC), 97 Gossett, W., and Student t test, 223 Government, U.S., See U.S. entries Government publications, cited as reference, 292t, 295, 311–314, 321 graft inﬁx in copolymer names, 243 Grammar overview, 41–50, 105–108 See also speciﬁc aspects Grammatical rank, deﬁnition, 46 Grant agencies’ manuscript submission systems, 60, 65, 67t Grant numbers, in “Acknowledgments” section, 24 Graphic artwork, See Artwork, Illustrations Graphics Interchange Format, See GIF format Graphs editorial process, 29 examples, 358f, 359f types of artwork, 347 when to use, 344 working with, 363 Grayscale line art deﬁnition, 347 example, 349f ﬁle formats, 352 working with, 347, 363 ➤ 405 “Greater than” vs “in excess of ” or “over”, 51 Greek letters alphabet, 214 for bonding orbitals, 256 in Boughton system for isotopes, 266 for chemical and physical terms, 155 in locants and descriptors, 233, 235, 238t, 240 in mathematical copy, 214 for subatomic particles, 256 in titles and headings, 150 in unit modiﬁers, 142 See also speciﬁc letters Greek multiplying preﬁxes, hyphenation, 136–137 “Green book” (IUPAC), 255 Grid marks in ﬁgures, 359 “Group” as collective noun, 106 lowercased for periodic table references, 261 Group names, isotope position, 265 Group numbers, periodic table references, 261 Grouping of digits in long numbers, 207–208 Grouping words, 50–51 Gunda, Tamas, software reviews by, 380 H in chemical names, 235 η (eta) in chemical names, 235 Halftone art deﬁnition, 347 example, 348f working with, 347, 360–362, 363 See also Figures, Photographs Handbooks description, 18 standard format, 19 Hapticity, η to indicate, 235 Hard copy checking proofs, 34b, 36 ﬁgure printing, 353b, 360 ﬁgure submission, 364 manuscript submission, 31 proofreaders’ marks and sample, 36–39 reprint orders, 35 table submission, 374 Hard returns, avoiding in tables, 374 Hazards, identiﬁcation of, 13, 21, 23 “He”, gender-neutral alternatives, 57, 58 Headings capitalization, 148–151, 227, 237t–239t parallelism, 48, 371 Hebrew surnames, 152 Helping verbs, in compound sentences, 108 Helvetica typeface, 356b, 363 Hermann–Mauguin symbols, 269 HighWire Press, editorial systems, 60, 69t 406 ➤ The ACS Style Guide “His”, gender-neutral alternatives, 57, 58 “Home Page” designation for citations, 320 Host organization information for Web sites, 321 HTML (hypertext markup language), 89–90, 98 “http://”, See Uniform resource locator HTTP protocol, electronic submission of manuscripts, 61 Hungarian surnames, 153 Hydrogen, H in chemical names, 235 Hydrogen bonds, representation, 244, 267 Hydrogen ion concentration, negative logarithm of, 271–272 Hydroxide ion concentration, negative logarithm of, 271–272 Hydroxyl group, attachment of, 244 Hyperlinks reference errors as issue, 24, 30, 31 supporting information availability, 25 Hypertext markup language, 89–90, 98 Hyphenation ACS desk reference use, 135 in amino acid sequences, 245 in CAS Registry Numbers, 254 with CASSI abbreviations, 295 chemical names at end of line, 233, 241, 247–249 color combinations, 125, 140 compound words, 138–139 e-mail addresses, 157 foreign phrases as unit modiﬁers, 139 with isotope names or symbols, 264–266 locants and descriptors, 234–236, 240, 241, 270–271 of position numbers, 246 preﬁxes, 135–137, 152, 240, 247–249 proper nouns and adjectives, 137, 138, 143, 152 spelling recommendations list, 129–133 sufﬁxes, 137–138, 151, 152, 247–249 surnames, 139, 152–153 syllabic portion of chemical names, 233, 240, 241 two-word vs phrasal verbs, 139 unit modiﬁers, 138, 139–143 with unit of measure, 141–143 Web addresses, 156 “I”, writing style, 43–44 i (imaginary number), 213 “Ibid.” in reference lists, 298, 326 “-ics” ending for nouns, 107 ICSD database, 284 “Idem” in reference lists, 298, 326 “Identical to” and “identical with”, 49 Identiﬁcation numbers, CAS Registry Numbers, 91, 94, 253–254 Identiﬁers in markup languages, 92, 94 Idioms used in comparisons, 49–50 “i.e.”, 117, 160 “II” or “III” in personal names, 117, 291, 301, 309, 312 “Ill”, hyphenation in unit modiﬁers, 141 Illustrations adapted, 84b, 366 combinatorial chemistry representation, 251 datument potential, 98 editorial process, 33, 363–365 electronic submission of manuscripts, 60, 61, 69t, 364 handling tips, 364–365 labeling for editorial processing, 362, 364 permission requirements, 83–86, 366 prescreened and rescreened, 362, 363 submitting, 363–365 types of, 29, 347–349 See also Artwork, Figures, Photographs Illustrator (software), 351–352, 363 Image ﬁle formats, See Computer ﬁle formats “Impact” vs “affect” or “effect”, 52 “In”, with titles in reference citations, 300, 301 “In excess of ” vs “greater than” or “more than”, 51 “In press” references, 315 “in.”, unit of measure, 118, 223 “Inc.” in publisher name, 303 InChI (International Chemical Identiﬁer), 91, 94, 101–102, 383 “Including”, restrictive and nonrestrictive uses, 116 Indeﬁnite pronouns, subject–verb agreement, 107–108 Independent clauses deﬁnition, 42 semicolon use, 119–120 Independent contractors and copyright, 78 See also Works made for hire and copyright “Independently”, 55 Index, mathematical concept, 211 Indexes of chemical substances and formulas, 253, 254 Indexing and abstract content, 21 and byline format, 21 and foreign surname format, 152 and title wording, 20 of U.S. government publications, 312 Web-based search engine use, 383 Indices, crystallographic, 267–268 Inﬁnitive phrases as sentence modiﬁers, 113 Index Inﬁnitives capitalization, 149 as sentence modiﬁers, 113 split, 43 Informal tables deﬁnition, 370 submitting, 374 See also Tables Information components, description, 99 Information for authors, See Author guidelines Information retrieval abstract content as factor, 21 title wording as factor, 20 See also Databases, Indexing, Literature searches Initials byline format, 21 in e-mail addresses, 157 in foreign names, 152, 153 for genus name, 160 period use and spacing, 119 reference format, 153, 291, 301, 309, 312 Ink cartridges for ﬁgure artwork, 353b, 360 Inkjet printers Excel ﬁgure speciﬁcations, 353b TrueType font format, 357b Inorganic compounds, capitalization examples, 237t Inorganic crystal structures, data sources, 284 Inorganic molecules, CIF format requirement, 284 Institutional and organizational names byline format, 21 capitalization, 147 reference format, 301, 307, 308, 312, 321 See also Company names, Publisher names Instructions for authors, See Author guidelines Instrumental diagrams as supporting information, 25 “Insure” vs “assure” or “ensure”, 52 Integrity issues, See Ethics entries Intellectual property and DOI use, 317 See also Copyright, Patents, Permissions inter inﬁx in copolymer names, 243 Interchange of structure data, 381 Intermediates, in combinatorial chemistry, 251 Intermetallics, crystal structure data sources, 284 International aspects of research and publishing, 59 International Bureau of Weights and Measures, 255 International Chemical Identiﬁer, See InChI International CODEN Directory, 340 International Committee on Weights and Measures, 228 ➤ 407 International Organization for Standardization (ISO), 255, 276, 294 International System of Units, See SI units The International System of Units (SI), 255 International Union of Biochemistry and Molecular Biology, 233 International Union of Crystallography (IUCr), 63, 284, 286 International Union of Pure and Applied Chemistry (IUPAC) centered dot spacing style, 261 chemical conventions, 255 chemical terminology, 97 compound nomenclature, 233 and InChI, 101–102, 383 structure representation standards, 383 unnamed elements, 260 Internet citation of Internet sources, 292t–293t, 314, 316–322 terminology list, 163–168 See also Electronic source citation, Web entries, World Wide Web sites Interviews, punctuation, 122 Introductions in scientiﬁc papers, 7, 22 Introductory words and phrases, 48, 114 Investigator integrity issues, See Ethics entries Iodine symbol, avoiding confusion with numerals, 262 Ion concentrations, negative logarithms of, 271–272 Ionic charges, indicating, 262, 266 IR spectroscopy, reporting analytical data, 275 “Is” instead of equal sign, 211 ISIS/Draw (software), 379–380, 380b, 382b ISO, See International Organization for Standardization “iso” preﬁx, style for, 236 Isolation of products and intermediates, 251 Isotopes “a” or “an” before, 257, 264 labeling, 264–266 mass numbers, 261, 263 modiﬁed vs unmodiﬁed compounds, 264 substituted compounds, 264, 265 Issue information in references, 296 Italic type in Boughton system for isotopes, 266 with CASSI abbreviations, 295 for chirality symbols and symmetry site terms, 270 combinatorial chemistry representation, 246 in copolymer names, 243 in crystallography, 269–270 for deﬁnitions, 154 for emphasis, 153 408 ➤ The ACS Style Guide Italic type—continued for genotypes, 154 group names indicating isotope position, 265 in locants and descriptors, 233, 234–236 m for molal, 155 in mathematical copy, 160, 212, 223 for orbital axes, 256 plurals of abbreviations ending in, 161 in polycyclic aromatic compounds, 240 reference citation guidelines, 30, 287 references to books, 154, 301, 306 references to computer programs, 323 references to meetings and conferences, 308 references to periodicals, 154, 294, 296, 298–299 references to technical reports and bulletins, 314 references to U.S. government publications, 312 for restriction endonucleases, 155 in subscripts or superscripts, 216, 373 for taxonomic names, 154, 160 for word’s ﬁrst occurrence, 154 IUCr, See International Union of Crystallography “ium” in element names, 260 IUPAC, See International Union of Pure and Applied Chemistry Japanese surnames, 153 Jargon, avoiding, 20, 54 JMol (software), 379, 380b Joint Photographic Experts Group format, 351, 352t, 357b Journal articles (in general) artwork sizing, 354, 370, 373 CIF format, 285–286 description, 18 standard format, 19 structure representation future, 383 translations, 299 word choice, 50 See also ACS journals and magazines, Manuscript entries, Scientiﬁc papers Journal as reference article titles, 291, 292t author names, 291, 297–299 CASSI abbreviations, 291, 292–293, 328–339 CASSI sample entry, 340–341 commonly cited journals, 328–339 examples, 292t–293t foreign-language journals, 299 generic format, 291 multiple parts, sections, and series, 295 repeated information, 297–298 same main title, 295 Journal as reference—continued special situations, 299 volume information, 295, 296, 297–298 See also Periodical as reference, References Journal editors, See Editors Journal of Combinatorial Chemistry, 246, 251 Journal presentations standard format, 19–20 types of, 18–19 See also ACS journals and magazines, Manuscript entries, Scientiﬁc papers Journal titles foreign-language journals, 299 italic type use, 154 series titles as, 306 JPEG format, 351, 352t, 357b “Jr.” and “Sr.”, 117, 291, 301, 309, 312 Judicial decisions on copyright, 80, 82 Kappa (κ) in chemical names, 235 “Kappa” vs κ, 155 Kelvin, degree symbol not used with, 227 Ketones, capitalization examples, 237t Keys to artwork symbols, 356, 365 Keywords in article titles, 20 for series publications in CASSI, 306 Kinetics, symbols and SI units, 277–278 Kingdom names (taxonomic), capitalization, 145–146 Kirk-Othmer Encyclopedia, cited as reference, 305–306 Korean surnames, 153 L in chemical names, 236, 245, 270–271 Labeling of axes on illustrations, 225, 359–360 of computer disks, 364 of illustrations for editorial processing, 362, 364 isotopic, 264–266 numeral use, 206, 289, 325, 345, 365 of speculations, 7 See also Numbering Laboratory reagents, See Reagents Language issues, See Word usage Laser printers Excel ﬁgure speciﬁcations, 353b TrueType font format, 357b Latin multiplying preﬁxes, hyphenation, 136–137 Latin terms abbreviations, 158–159 plural forms, 128 roman type use, 154 See also Taxonomic terms Index Lattices, crystallography, 268, 269 Laue indices, crystallography, 267 Laws cited as reference, 313 copyright laws, 77–82 Laymen, word choice for, 16 Legends for artwork symbols, 356, 365 Length of manuscript, limiting, 5, 25, 32 “Less” vs “fewer”, 51 Letters (journal presentation type), 18 “Levels” with plurals of symbols, 211 Libraries, combinatorial, 246, 250–252 Licensing arrangements and copyright, 82 Ligating atom, κ to designate, 235 Ligation sites, 234 “like”, hyphenation as sufﬁx, 138 Limits, mathematical spacing, 219 Line art deﬁnition, 347 example, 348f ﬁle formats, 352 working with, 347, 354–360, 363 See also Figures Line breaks e-mail addresses, 157 equations, 220 reaction schemes, 379 Web addresses, 156 Line graphs color use, 345b examples, 358f types of artwork, 347 when to use, 344 working with, 363 Line returns, avoiding hard returns in tables, 374 Line styles for ﬁgures, 345b, 358 for structures, 378 Line width for ﬁgures, 353b, 355, 358, 363 for structures, 378 Linear vs angular formulas, 267, 376 Lines (geometric) in mathematical copy, 213, 223 Liquid state, indicating in reactions, 272 Lists numbered, 123, 206–207 parallelism, 48 vs tables, 370, 374 See also References, Series items Lists, editorial abbreviations, acronyms, and symbols, 169–202 abbreviations not needing deﬁnition, 158– 159, 217–218, 260 ➤ 409 Lists, editorial—continued CASSI journal abbreviations, 328–339 chemical name hyphenation, 247–249 computer and Internet terms, 163–168 geometric notation symbols, 223 Greek alphabet, 214 mathematical operators and symbols, 217–218 multiplying preﬁxes, 136–137, 240 non-SI units, 231t, 232t physical quantities and symbols, 277–283 plurals, tricky, 128 polymer names, 242 postal abbreviations, 161–162 preﬁxes not to be hyphenated, 135–136 scientiﬁc preﬁxes, 135–136, 235 set notation symbols, 222 SI and SI-derived units, 229t–230t spelling and capitalization recommendations, 129–133 statistical symbols, 223 surnames as modiﬁers, 152 surnames as units of measure, 152, 225 transport properties, 212 trigonometric and other functions, 213 unit modiﬁers, 140 words and phrases to avoid, 54–55 Literary vs scientiﬁc writing, 28 Literature reviews, See Review articles Literature searches author obligation for, 13 reference management programs, 326 “Little”, hyphenation in unit modiﬁers, 141 Local government publications, cited as references, 313–314 Locants capitalization, 145, 238t–239t, 240 and chirality, 270 hyphenation, 234–236, 240, 241, 270–271 and isotopic labeling, 264–266 for saccharides, 243 style guidelines, 234–236 types of, 233 Logarithms of ion concentrations, 271–272 Loose-leaf services, 314 “-ly” words, hyphenation, 141 m for molal, 155 M for molar, 155, 271 Machine-understandable information and data, See Datuments, InChI Macintosh platform reference manager programs for, 327 templates for, 29 Macromedia software, 351–352, 363 Macromolecular CIF format, 284 410 ➤ The ACS Style Guide Macromolecular structure data sources, 284 Magazines, See ACS journals and magazines, Periodical as reference Magnetism and electricity, symbols and SI units, 278–279 “Man”, gender-neutral alternatives, 57–58 Manufacturer names, parentheses use, 22, 124 See also Company names Manuscript Central (software), 60, 62, 69t Manuscript conﬁdentiality, 9, 12, 15, 16, 73–74 Manuscript format standards, See Standard format for scientiﬁc papers Manuscript marking by proofreaders, 36–39 Manuscript processing stages accepted manuscripts, 33–35 draft manuscripts, 27–31 ﬁnal manuscripts, 32–33 proofreaders’ marks, 36–39 resubmission of manuscripts, 76 review, 31, 71–76 See also Editorial process, Electronic submission of manuscripts Manuscript review, See Peer review Manuscript submission, See Electronic submission of manuscripts, Manuscript processing stages Manuscript templates, See Templates “Many”, subject–verb agreement, 108 Marking proofs, 34b, 36–39 Markup languages, See Datuments, speciﬁc languages Mass numbers, 261, 263–264 Mass spectrometry, symbols, 266 Mass spectroscopy, reporting analytical data, 275 Material Safety Data Sheets (MSDSs), 292t, 315 Materials, identiﬁcation in text, 22 “Materials and Methods” sections, 22–23 Mathematical arguments, See Arguments (mathematical) Mathematical concepts, deﬁnitions, 210–211 Mathematical constants as concept, 210 deﬁning symbols in text, 211 Greek letter use, 214 italic type use, 212 roman type use, 213 standard abbreviations and symbols, 211, 217–218 Mathematical derivations, 23, 25 Mathematical derivatives, 219, 220 Mathematical equations, See Equations Mathematical expressions in superscripts and subscripts, 217 Mathematical expressions in text numeral and word usage, 205, 206 punctuation, 124 when to use, 220 Mathematical operators as concept, 210 link breaks after, 220 roman type use, 212 spacing considerations, 214–215, 217, 219, 222 standard abbreviations and symbols, 217–218 See also Mathematical symbols, Minus sign, Plus or minus sign (±), Plus sign, Times sign (×) Mathematical papers, sentence modiﬁers in, 112 Mathematical symbols abbreviations differentiated from, 160, 211 case sensitivity, 159 deﬁning in text, 211 italic type use, 160, 212, 216 not needing deﬁnition, 211, 217–218 plural forms, 211 spacing as adjectives, 215 specialized notation, 222–223 See also Abbreviations, Mathematical operators, Symbols, Units of measure, speciﬁc symbols Mathematical variables as concept, 210 deﬁnitions after equations, 225 deﬁnitions in text, 211 Greek letter use, 214 italic type use, 212 roman type use, 213 spacing between, 215, 219 Mathematics usage and style abbreviations, 211, 217 boldface type, 213 enclosing marks, 214–216, 217 equations, 218–222 geometric notation, 223 Greek letters, 214 italic type, 160, 212, 223 mathematical concept deﬁnitions, 210–211 ratio and mixture notation, 222 roman type, 212–213, 214, 223 script and open-faced letters, 214 set notation, 222 spacing, 214–215 statistics, 223 subscripts and superscripts, 216–217 symbols, 211, 217–218 Index Matrices boldface type for matrices, 213 italic type for elements, 212 as mathematical concept, 210, 211 roman type for transposes, 213 MDL molﬁle format, 382 MDL software, 380b “Me” vs “myself ”, 51 Measure, units of, See Units of measure Mechanics, symbols and SI units, 280 Meeting and conference presentations reference format, 56–57, 292t, 307–309, 321, 323 standard reporting format, 19 types of books, 17 Meeting references, “Acknowledgments” section contents, 24 Melting points, reporting analytical data, 274 Members, in combinatorial chemistry, 250–252 Merriam-Webster’s Collegiate Dictionary, 127, 135 Metadata datument as scientiﬁc grid component, 99–100 deﬁnition, 89–90 Metal-organic crystal structures, data sources, 284 Metals, crystal structure data sources, 284 “Methods” as CASSI keyword, 306 “Methods” sections, 22–23 Metric system, background of, 228 Metric units, technical documents usage, 223 Microsoft font format, 357b Microsoft software electronic submission of manuscripts, 61 ﬁgure prepration, 352, 353b, 363 structure preparation, 379 table preparation, 373 Miller indices, crystallography, 267 Millions, 204, 210 Minus sign and chirality, 271 for electric charge, 256 for ionic charge, 262, 266 for optical rotation, 270 as stereochemical descriptor, 236 structure preparation, 379 Minutes symbol, spacing, 203, 224 Mirror plane, crystallographic symbols, 269 Misplaced modiﬁers, 44 Mixtures amino acid representation, 244 combinatorial chemistry representation, 246, 250–252 notation, 222 punctuation, 121, 126, 222, 261 ➤ 411 MKSA system, background of, 228 mmCIF format, 284 Model numbers capitalization, 147 numerals used as names, 206 parentheses use, 22 Modeling programs as supporting information, 25 Modiﬁcation, isotopic, 264 Modiﬁers dangling, 45, 109–112 misplaced, 44 prepositional phrase, 49 sentence, 44–45, 112–113 surnames as, 151 See also Adjectives, Unit modiﬁers Mol Draw (software), 380b Molecules CIF format requirement, 284 datument potential, 88, 99 electronic conﬁguration, 257 InChI identiﬁers, 91, 94, 101–102 isotopic substitution, 264 markup languages and the WWW, 91, 92–94, 95f, 96 modeling coordinates as supporting information, 25 nuclide descriptors, 261–263 symbols and SI units, 277 molﬁle format, 382 Monetary values, U.S., 208 Monographs description, 18 editorial process, 33 standard format, 19 Monosaccharides, abbreviations, 243t Month abbreviations, 160–161 “Moon”, capitalization, 148 “More than” vs “in excess of ” or “over”, 51 “Most”, subject–verb agreement, 108 Movies still shot permissions, 83 Web-enhanced objects, 25, 26 MSDSs (Material Safety Data Sheets), 292t, 315 “Mu” (µ), spelling out, 155 Multidimensional physical quantities, boldface type use, 213 Multiple authors author home page, 62 book categories, 17, 18 byline format, 21 editorial process, 33 ethical issues, 6–7, 14 reference citation format, 289 reference collation, 325 references to books, 300–301 412 ➤ The ACS Style Guide Multiple authors—continued references to periodicals, 291 U.S. government publications, 312 See also Authorship Multiple preﬁxes, hyphenation, 136 Multiplication asterisk use, 211 with compound units of measure, 224 spacing guidelines, 215, 219, 224 Multiplication sign (×), 215 Multiplying preﬁxes hyphenation, 136–137, 240 numbers style, 207 SI system, 229t spacing considerations, 226 Multisyllabic words, hyphenation of sufﬁxes, 138 Multiword concepts, en dash use, 124–125 Mutation, designation of, 246 “My”, writing style, 44 myICAAP (software), 60 “Myself ” vs “me”, 51 N- vs N-, when to italicize, 235 n before volume number in CASSI, 295 N for normal, roman type use, 155, 271 “Namely”, comma use, 117 Names of persons, See Author names in references, Author names in text, Personal names Namespaces (CML component), 92 Naming of chemical compounds, See Chemical names, Chemical nomenclature National Academy of Sciences, 4 National Institute of Standards and Technology, 228, 255 National Institutes of Health, 10 National Science Foundation, 10 Negative electrons, indicating, 256 Negative exponents for division, 224 Negative logarithms of ion concentrations, 271–272 Negative numbers, “to” or “through” with, 125, 209 “Neither”, subject–verb agreement, 107 “Neither … nor”, 47 “neo” preﬁx, style for, 236 Nesting order for enclosing marks, 216 Net plane, crystallographic symbols, 268–269 Newsgroups, electronic, 293t, 322 Newspapers nonscientiﬁc periodicals, 292t, 299 special typefaces, 154 “nil” in element names, 260 NMR spectroscopy reporting analytical data, 274–275 symbols and SI units, 281 “No one”, subject–verb agreement, 107 “No.” in references, 295, 304 “no.” in unit of measure, 118 “Non”, hyphenation as preﬁx, 137 Non-English terms, plural forms, 128 Non-native English speakers as writers, 28, 75 Non-SI units, lists, 231t, 232t “None”, subject–verb agreement, 108 Nonexclusive rights arrangements, 82 Nonhyphenated preﬁxes, 135–136 Nonrestrictive phrases or clauses comma use, 44, 109, 116 em dash use, 126 grammar overview, 109 Nonscientiﬁc periodicals, citing, 292t, 299 Nontechnical style for numbers, 203, 204, 205 “Nor” as coordinating conjunction, 47, 113, 149 “Not … but”, 47 “Not only … but also”, 47 Notation ChemSet notation, 246, 251–252 mathematical, 222–223 scientiﬁc, 207, 209–210 See also Abbreviations, Symbols “Note” line in table footnotes, 373 Notes (journal presentation type), 18 Nouns “-ics” ending, 107 collective, 106–107 hyphenation and proper nouns, 137, 138 phrasal verbs as, 139 possessives, 127 predicate, 108 proper, 137, 138, 143, 152 as unit modiﬁer element, 139–140, 143 Nuclear chemistry, atomic number use, 262 Nuclear reactions, reaction scheme, 273 Nucleic Acid Database, 284 Nucleic acids, abbreviations, 244t Nucleosides, abbreviations, 244t Nucleotides, sequence presentation, 244 Nuclide descriptors, atoms and molecules, 261–263 Nuclides, isotopic, 264 Number of atoms, 263 of the subject, 44, 105–108 “Number” as collective noun, 106 Number–unit of measure combination as singular, 51 Numbered lists, 123, 206–207 Numbering of charts, 206, 377 of chemical species in text, 206 of equations and reactions, 206, 220, 272, 377 Index Numbering—continued of ﬁgures, 206, 345, 365 in nucleotide sequences, 244 of references, 206, 289, 325 of schemes, 206, 346, 378 of structures, 206, 246, 346, 375–377 of tables, 206, 369 Numbers agency report numbers, 312 atomic numbers, 258t–259t, 260, 262 at beginning of sentence, 204 CAS Registry Numbers, 91, 94, 253–254 charge numbers for ions, 262 chemical concentrations, 271–272 comparison words, 51 coordination numbers, 270 crystallographic point groups, 269 data entry numbers, 314, 320, 324 en dash use, 125, 209 of ﬁve or more digits, 207–208 of four or more digits, 207 fractions, 108, 139, 205, 208, 217, 219 government publication numbers, 312 group numbers, 261 hyphenation as unit modiﬁers, 141–143 large numbers, 204, 207–208, 210 mass numbers, 261, 263–264 model numbers, 22, 147, 206 negative, “to” or “through” with, 125, 209 nontechnical style, 203, 204, 205 numeral and word usage, 203–207 ordinal numbers, 203–204, 205, 308 oxidation numbers, 262–263 parallelism in sentence, 204 patent numbers, 208, 310 position numbers, 246 position of atoms, 263 quantum numbers, 257 retaining parts of in ranges, 209–210 single, in unit modiﬁers, 142, 143 of species in reactions, 272 species numbers, 272 spelling out vs numerals, 160, 203–205 of standards, 276 style overview, 207–210 unit of measure spacing with, 203, 223–224, 271–272 See also Fractions, Numerals, Reference citation numbers Numbers of atoms, subscript use, 263 Numerals with “a.m.” and “p.m.”, 205 arabic vs roman, 206, 369, 375–378 for artwork labeling, 206, 345, 365 in Boughton system for isotopes, 265–266 in bridged and spiro alicyclic compounds, 236 ➤ 413 Numerals—continued chemical species identiﬁcation, 206 crystallographic point groups, 269 in dates, 160, 205 decimal point guidelines, 208, 372 designation digits for superatoms, 246, 250–251 ellipses use, 127 en dash use, 125 for equation labeling, 289 expressions used in mathematical sense, 205 hyphenation of preﬁxes and sufﬁxes, 137, 138 in locants and descriptors, 233, 234, 236, 238t, 240 mathematical use and italic type, 212 as names, 206 numeral and word usage, 203–207 for oxidation numbers, 262–263 in ranges, 125, 204, 209–210, 296 in ratios, 205 for reference labeling, 206, 289, 325 in series, 123, 127, 204, 206–207, 209 for species numbers, 272 spelling out vs numerals, 160, 203–205 See also Numbers, Reference citation numbers Numerical roots in element names, 260 “N.Y.”, CASSI spacing exception, 294 o- vs O-, when to capitalize and italicize, 145 O- vs O-, when to italicize, 235 O for products separate, 246, 251, 252 Ofﬁce of Research Integrity, U.S. Department of Health and Human Services, 4 Ofﬁcial titles in bylines, 21 capitalization, 147–148 Oligonucleotides, data sources, 284 Oligosaccharides, representation of, 244 “On the basis of ” vs “based on”, 52, 111 Online books, 293t, 314, 319–320 See also Web-based publications “Online” designation for citations, 318–319 Online information, See Electronic source citation, Internet, Web entries, World Wide Web sites Online periodicals, 292t–293t, 297, 298, 317–319 See also Web-based publications Online submission of manuscripts, See Electronic submission of manuscripts “Only”, placement effects on meaning, 45 Ontologies datument as scientiﬁc grid component, 99 deﬁnition, 98 414 ➤ The ACS Style Guide Open-faced letters, 214 Open Journal Systems, 60 OpenType fonts, 357b Operators, See Mathematical operators Optical rotation in chemical names, 270 “Or” vs “and/or”, 56 as coordinating conjunction, 47, 113, 149 number of subject, 106 slash misused for, 56 Oral presentations citation guidelines, 307, 321 converted to scientiﬁc papers, 57 Orbitals, chemical conventions, 256–257 Order names (taxonomic), capitalization, 146 Ordinal numbers, 203–204, 205, 308 See also Numbers Organic compounds, capitalization examples, 237t Organic crystal structures, data sources, 284 Organic groups, common abbreviations for, 260 Organic Syntheses, cited as reference, 305 Organizational names, See Institutional and organizational names Orientation of artwork on page, 353b, 364, 370 Original research, reports of, See Scientiﬁc papers “Our”, writing style, 44 “Over” vs “greater than” or “more than”, 51 Overbar for crystallographic point groups, 269 Overview chapters in proceedings volumes, 17 Oxidation numbers, chemical conventions, 262–263 “p” and “pp” in pagination, 304 Page lengths for ACS publications, 354t Page number citations books, 304 data sets, 314 DOI use, 317 numbers style, 208 periodicals, 296–297 U.S. government publications, 312 Page proofs, marking of, See Proofreaders’ marks and sample markups Paper copy, See Hard copy “Paper” in references, 304 Paper number, references to meetings and conferences, 308 Paper stock for ﬁgure artwork, 353b Paragon Plus System, 30, 364, 374, 382b Paragon System electronic submission of manuscripts, 60, 62, 69t submission of artwork, 30, 364, 374, 382b Paragraphs, numbered, 207 Parallel constructions numeral and word usage, 204 in tables, 48, 371 writing style, 46–48, 50 Parallel synthesis, description, 252 Parameter settings for ACS publications, 381b Paraphrasing, ethical considerations, 7 Parent elements (markup language component), 91 Parentheses with abbreviations, 158, 160, 225 in axis labels on ﬁgures, 359 with chemical preﬁxes, 236 with chemical reactions, 272, 377 comma use, 115 with compound units of measure, 224 with credit lines, 367b with crystallographic indices, 267–268 with enumerations, 123, 206–207 with generic names, 23 for isotopic substitution, 264 with manufacturer names, 22, 124 in mathematical copy, 124, 212, 214–216, 219 in mathematical equations, 219–220 nesting order, 216 for oligosaccharides, 244 with optical rotation indicators, 270 with oxidation numbers, 262–263 in polymer or complex chemical names, 146, 151 with ranges in scientiﬁc notation, 209 reference citation guidelines, 30, 124, 209, 287, 289–290 references to books, 305 references to periodicals, 296 with standard deviations or standard errors, 208–209 with syllabic portion of chemical names, 240 Parenthetical expressions abbreviation use, 160 capitalization in titles and headings, 151 comma use, 117 hyphenation as unit modiﬁers, 143 parentheses use, 123 Parenthetical sentences, 123 Part number in book references, 304, 306 Participles as unit modiﬁer element, 140, 142, 143 Particles in foreign names, 152–153 Parts of a book, capitalization, 144 Passive voice avoiding, 42, 54 and dangling modiﬁers, 109, 110–111 as gender-neutral alternative, 58 Index Passwords for author home pages, 62, 68 Past participles as unit modiﬁer element, 142 Past tense, 42–43 Patent numbers citation guidelines, 310 style guidelines, 208 Patents cited as reference, 292t, 310–311 and publication timing, 5 PDF documents electronic submission of manuscripts, 60–61, 68 ﬁgure preparation, 351, 353b, 357b, 363 font tips, 357b Peer review author requests regarding, 13, 15–16, 72, 75 author responsibilities, 75–76 CIF validation reports, 63, 286 double-blind reviews, 71 editorial process, 29, 31, 32 electronic submission of manuscripts, 31, 59, 60, 63, 68 encouragement to new investigators, 76 ethical considerations, 5, 8–9 ethical guidelines, 15–16, 73, 74, 76 of journal presentations, 19 online article regarding, 71 PDF ﬁle suitability, 60–61 process of, 72–73 purpose of, 71–72 review forms, 73 reviewer ratings, 73 reviewer responsibilities, 73–74 topic suggestions, 74b Peer X-Press (software), 60, 62, 69t People as photographic subjects, 82, 361 “Per” in spelled-out units of measure, 225, 226 per inﬁx in copolymer names, 243 Percent sign, spacing, 203, 224, 271 Period with abbreviations or acronyms, 118, 119, 223, 294 in bridged and spiro alicyclic compounds, 236 with CASSI abbreviations, 294 as decimal point, 208 in declarative sentences, 118 in e-mail addresses, 157 with ellipses, 126 with “et al.”, 289 with parenthetical sentences, 123 with quotation marks, ACS policy, 122 reference citation guidelines, 289–290 references to books, 301–306 references to periodicals, 291, 294, 297–299 references to theses, 309 ➤ 415 Period—continued references to U.S. government publications, 312–313 with units of measure, 118, 223 in Web addresses, 156 “Periodic table”, capitalization, 261 Periodical as reference abstracts, 298–299 article titles, 291, 292t author names, 291, 297–299 CASSI abbreviations, 291, 292–293, 328–339 CASSI sample entry, 340–341 examples, 292t–293t Federal Register citations, 313 generic format, 291 nonscientiﬁc magazines and newspapers, 292t, 299 online periodicals, 292t–293t, 317–319 organization or committee as author, 307 pagination information, 296–297 place of publication, 294, 295 repeated information, 297 special situations, 299 volume information, 295, 296, 297–298 year of publication, 296, 297–298 See also References Periodical titles, italic type for, 154 Periodicals, ACS, See ACS journals and magazines Permission request form, ACS, 84b Permission request guidelines, ACS, 83–86, 366 Permission request guidelines, non-ACS copyrighted material, 83–86 Permissions from ACS Copyright Ofﬁce, 84b ACS copyright ownership beneﬁts, 86 from ACS Publications Division, 79b, 83, 84b credit line preferences, 85b, 86, 367b for e-mail and personal communications, 7, 14, 316 for electronic media, 81, 82, 83 fair use guidelines, 80–81 paperwork submission by author, 32, 33 for photographs of people, 82, 361 for previously published material, 30, 80, 83–86, 366 for unpublished material, 7, 12–13, 16 U.S. government works and public domain, 81 written request necessity, 83–86, 84b, 366 Person, agreement in, 44 Personal communications author obligation to obtain permission, 7, 14 e-mail citation format, 293t, 316, 322 general citation format, 292t, 316 See also Electronic mail (e-mail) 416 ➤ The ACS Style Guide Personal criticism, in scientiﬁc writing, 7–8, 14, 16, 74 Personal names byline format, 21 comma use, 117–118 in e-mail addresses, 157 en dash use, 125 foreign name format, 139, 152–153 hyphenation, 139, 152–153 period use, 119 possessives, 127 professional titles with, 21, 147–148, 152 as taxonomic name element, 146 See also Author names in references, Author names in text, Surnames Personal opinions, avoiding in writing, 44 pH, style for, 155, 271–272 Phenotypes, roman type use, 154 Phosphate group, attachment of, 244 Photocopying copyrighted material fair use and restrictions, 80 Photographs color prints, 362 combos, 347, 349f, 352t, 363 copyright, 81–82, 361, 366 example, 361f ﬁgure preparation, 360–362, 363 ﬁle formats, 350–352, 363 handling and labeling, 362, 364–365 of people, 82, 361 permissions, 82, 83, 361, 366 prescreened, 362 scanning tips, 355b, 362 types of artwork, 347 when to use, 344 See also Artwork, Illustrations Photon frequency, indicating, 272 Photoshop (software), 350–352, 355b Phrasal adjectives, 149 Phrasal verbs, 139, 149 Phrases, deﬁnition, 42 Phrases to avoid, 54–55 Phylum names, capitalization, 145–146 Physical quantities boldface type use, 213 italic type use, 216 as mathematical concept, 210 non-SI units, 231t SI-derived units, 229t, 230t SI units, 228, 229t symbols, 277–283 Physical terms, Greek letter use, 155 pi (π) as mathematical constant, 213 for positive proton, 256 Picas as space measure, 353b, 354t, 356b Pie charts color use, 345b types of artwork, 347 when to use, 344 working with, 363 Piece fractions, when to use, 205 See also Fractions Pixels per inch as measure, See Resolution of ﬁgure ﬁles Place of publication books, 303 data sets, 314 meetings and conferences, 308 periodicals, 294, 295 theses, 310 U.S. government publications, 312 Plagiarism, ethical considerations, 7, 10, 74 Planck’s constant, indicating, 272 Planes in crystals, 267–269 Planes (geometric) in mathematical copy, 212, 223 Planets, capitalization, 148 Plural forms of abbreviations, 161 of decades, 205 “eq” or “eqs”, 221 as gender-neutral alternative, 58 of mathematical symbols, 211 of numerals used as names, 206 possessives of, 127 taxonomic names, 146, 154 of trademarks, 157 tricky plurals, 128 of units of measure, 224, 225 Plus or minus sign (±) with standard error or standard deviation, 208–209 as stereochemical descriptor, 236 Plus sign vs “and”, 55, 211 with D and L forms, 271 for electric charge, 256 for ionic charge, 262, 266 for optical rotation, 270 as stereochemical descriptor, 236 structure preparation, 379 “Plus” vs “and”, 55 “p.m.”, 205 pOH, deﬁnition, 271 See also pH Point groups, crystallographic, 269 Points as type size measure in ﬁgures, 353b, 355, 356b, 358, 363 in structures, 378 in tables, 373 Index Points (geometric) in mathematical copy, 213, 223 “poly” preﬁx, capitalization, 146, 150 Polyatomic molecules, 257 Polycyclic aromatic compounds, 240 Polymer beads, representation of, 251 Polymer chemistry, symbols and SI units, 281 Polymer names capitalization, 146, 150, 237t, 242–243 copolymers, 243 nucleic acids, 244 roman type use, 242 Pools, in combinatorial libraries, 251–252 Popular literature, ethical guidelines for publication, 16 Portable Document Files, See PDF documents Position designations for stereochemical descriptors, 270 Position numbers after amino acid abbreviations, 246 Positional preﬁxes, 145, 235, 238t–239t, 240 Positions of atoms, 263 isotopic substitution and labeling, 264, 265 of nuclides, 264 of substituents, 246, 250 on sugar residues, 243 Positive protons, indicating, 256 Possessives, tricky, 127 Postal abbreviations, 161–162, 303, 310 Postdoctoral students and peer review, 9, 75 Poster presentations, citation guidelines, 307, 321 PostScript ﬁles, 351–352, 353b PostScript font format, 357b Powder diffraction analysis, CIF format requirement, 284 PowerPoint (software), 61, 352, 353b Powers of 10, 210 ppi as measure, See Resolution of ﬁgure ﬁles Predicate adjectives, 143 Predicate nouns, 108 Predicates, compound, 115 Preﬁxes to chemical names, 145, 235–236, 240–241, 245, 247–249, 270 to chemical terms, 137 to drug names, 145 hyphenation, 135–137, 152, 240, 247–249 multiplying preﬁxes, 136–137, 207, 226, 229t, 240 to numerals, 137 to proper nouns and adjectives, 137, 152 Prepositional phrases, with split idioms, 49 Prepositions, capitalization in titles and headings, 149, 150 ➤ 417 Preprint servers, citing articles retrieved from, 293t, 317, 319 Preprints citation format, 308 Prescreened illustrations, 362 Present participles as unit modiﬁer element, 142 Present tense, 43 Presentations, See Journal presentations, Meeting and conference presentations, Oral presentations “Press” in publisher name, 303 Press releases, disclosure of research results, 16 Primed numbering, 244 Primes, spacing considerations, 219 Printed copy, See Hard copy Printer’s errors, 34 Private communications, See Personal communications Proceedings volumes description, 17 reference format, 292t, 307–308, 321, 323 standard reporting format, 19 ProCite (software), 326–327 Production editing, role, 33 See also Editorial process, Editors Products, in combinatorial chemistry, 246, 251–252 Professional titles in bylines, 21 capitalization, 147–148 foreign surnames, 152 Programs, computer, See Software programs “Progress” as CASSI keyword, 306 Pronouns antecedents of, 45–46, 58 reﬂexive, 51, 113 Pronunciation, “a” vs “an”, 53, 257, 264 Proofreaders’ marks and sample markups, 36–39 Proofs checking, 33–35, 36 marking, 34b, 36–39 Proper adjectives, hyphenation, 137, 143, 152 Proper names adjectives formed from, 144 hyphenation in unit modiﬁers, 142, 143 hyphenation of preﬁxes and sufﬁxes, 152 possessives, 127 spelling recommendations, 127 See also Author names in references, Author names in text, Company names, Personal names Proper nouns, hyphenation, 137, 138, 143, 152 Proportionality in artwork, 355, 356, 358f See also Sizing of artwork 418 ➤ The ACS Style Guide Protein Data Bank, 284 Proteins, representations of, 154 Proton charges, indicating, 256 Province abbreviations, 161–162 Public domain status, determining, 81, 83 Public pronouncement of research results, 16 Publication information in references, See Place of publication, Publisher names in references, Year of publication Publication number, U.S. government publications, 312 Publication phase of editorial process, 34–35 Publication volume information in references, 295, 296, 297–298, 303–304, 306 Publicon (software), 99 “Publish or perish” mentality, 5 PublishASAP (software), 60 Publisher names in references acronym or abbreviation use, 302, 307 books, 302–303 data sets, 314 meetings and conferences, 308 organization or committee as author, 301, 307, 308, 312, 321 U.S. government publications, 312 Publishers’ guidelines, See Author guidelines Publishers’ manuscript submission systems, 60, 65t–66t, 68, 69t Publishers’ templates, See Templates Publishing agency information, U.S. government publications, 312 Punctuation in chemical names, 241 with display equations, 221 e-mail and Web addresses, 156–157 with quotation marks, ACS policy, 121–122 roman type in mathematical copy, 212 unit modiﬁers with same ending base, 141 See also Colon, Comma, Em dash, En dash, Period, Semicolon, Slash Pure and Applied Chemistry, 255 Qualiﬁers of personal names, 117, 291, 301, 309, 312 Quality vs quantity of research, 5 Quanta, chemical conventions, 256 Quantitative analysis, reporting data, 276 Quantities, Units and Symbols in Physical Chemistry, 255 Quantities and Units, 255 Quantum numbers, chemical conventions, 257 Quotation marks ACS policy on, 121–122 square brackets within, 124 use guidelines, 122 Quotations added material, 124 colon use, 144 comma use, 118 ellipses use, 126 ethical considerations, 7 interviews, 122 quotation marks use, 121–122, 124 spelling recommendations, 127 See also Extracts (textual) R and R∗ preﬁxes in chemical names, 236, 270 R for sets of substituents or residues, 246, 250–251 “rad” vs “rd” and “radian”, 225 Radiation, symbols and SI units, 282 Radical sign in running text, 217 Radicals, free and charged species, 266 ran inﬁx in copolymer names, 243 Ranges en dash use, 117, 125, 209, 289 numeral and word usage, 204, 209–210 pagination information in references, 296, 304 units of measure as ﬁnal item, 226 Rank, grammatical, 46 Rapid Review (software), 60, 62, 69t RasMol (helper application), 25 Ratios isotopic, 265 notation, 222 numeral use, 205 punctuation, 121, 222 spacing considerations, 215, 219 “rd” vs “rad” and “radian”, 225 RDF (Resource Description Framework), 99–100 RDF Site Summary (RSS), 100 Reaction names preceded by element symbols, 145, 234, 240–241 Reactions, See Chemical reactions, Nuclear reactions, Schemes Readers, ethical obligations of, 9–10 Reading column in tables, 371, 372t Reagents in combinatorial chemistry, 246, 250–252 identiﬁcation in text, 22, 23 Recasting sentences for active voice, 42, 54 to avoid beginning with number, 204 for gender-neutral language, 57–58 words and phrases to avoid, 54 “Recently”, 57 Red–green–blue (RGB) color mode, 350, 352, 362 Refereeing of scientiﬁc papers, See Peer review Index Reference books used by ACS staff, 127, 135 Reference citation numbers formatting, 30, 287 punctuation, 117, 124, 209, 289 See also Reference numbering Reference citations in text abstract guidelines, 22 ACS styles, 287–290 citation manager programs, 326–327 editorial process, 30–31 multiple references by same author, 290 parentheses use, 124 permission requests, 85b, 366 placement in sentence, 290 reporting analytical data, 276 spacing of page numbers, 208 Reference Manager (software), 326–327 Reference manager programs, 326–327 Reference numbering arabic numeral use, 206 citation guidelines, 289 collating references, 325 See also Reference citation numbers References “a” and “b” references, 290, 297–298, 325 abstracts, 298–299, 308, 321 article titles, 291, 292t author names in, See Author names in references author responsibility, 24, 30, 31, 290 books, 290, 292t–293t, 300–306, 319–320, 323–324 CASSI abbreviations, 291, 292–293, 313, 328–339 CASSI format for abstracts and proceedings, 308 CASSI format for computer programs, 324 CASSI sample entry, 340–341 chapter titles, 301, 306, 312 collating, 290, 325–326 committees as authors, 301, 307 as copyright ownership indicator, 81 data sets, 314–315 editor names, 292t, 293t, 300–302, 320 editorial process, 30–31 electronic sources, 292t–293t, 297, 298, 316–325 errors in, 24, 30, 31 ethical obligations of authors, 7, 13, 14 ethical obligations of reviewers, 15 examples, 292t–293t foreign surname format, 152 government publications, 292t, 295, 311– 314, 321 in illustrations, 289, 373 management programs for, 326–327 ➤ 419 References—continued Material Safety Data Sheets, 292t, 315 material without publication information, 308–309 meeting and conference proceedings, 56–57, 292t, 307–309, 321, 323 minimum data, 290, 306, 309, 310 miscellaneous information, 305 nonscientiﬁc periodicals, 292t, 299 organizations as authors, 301, 307, 308, 312, 321 pagination information, 208, 296–297, 304 patents, 292t, 310–311 periodicals, 290–299, 292t–293t, 317–319 place of publication, 295, 303 placement in manuscript, 24 publisher names in, See Publisher names in references repeated information, 290, 297–298 series publications, 292t, 304, 305–306 special situations, 299, 305–306 technical reports and bulletins, 292t, 314, 324 theses, 292t, 309–310, 321, 324 unpublished materials, 308–309, 315–316, 321 volume information, 295, 296, 297–298, 303–304, 306 year of publication, 296, 297–298, 303 See also Book as reference, Journal as reference, Periodical as reference “References therein”, use in citations, 297 Reﬂexive pronouns, 51, 113 RefWorks (software), 326–327 Regions of the country, capitalization, 148 Registered trademark symbol, See Trademark symbol Registry Numbers, CAS, 253–254 Regulatory agencies, commercial chemical inventories of, 254 Rejection of manuscripts author guidelines, 75 ethical considerations, 12 reasons for, 72, 73, 75–76 “Relative to”, 50 Religious titles in bylines, 21 Repetitive research reports, 5 Report numbers, U.S. government publications, 312 Reports, technical, 292t, 314, 324 Reports of original research, See Scientiﬁc papers Reprinting, permissions for, See Permissions Reprints, for authors, 35 Reproducibility of results ethical considerations, 5–6, 8, 13 mathematical detail in papers, 23 420 ➤ The ACS Style Guide Reproduction artwork, 29, 83–86, 366 photographs, 360–362, 363 See also Permissions Rescreening of illustrations, 363 Research articles, See Journal articles Research errors, See Errors Research ethics issues, See Ethics entries Research grant agencies’ manuscript submission systems, 60, 65, 67t Research reports, See Scientiﬁc papers Residues in combinatorial chemistry, 246, 250–251 of saccharides, 243, 244 Resolution of ﬁgure ﬁles Excel tips, 353b and ﬁle formats, 351–352 graphics from Web sites, 364 photographs and halftone ﬁgures, 360–362 and publication medium, 346 scanning tips, 355b structure graphics, 378, 379, 382b and type of artwork, 347 Resonance structures, arrows for, 272 Resource Description Framework (RDF), 99–100 “Respectively”, 50, 55 Restriction endonucleases, 155 Restrictive phrases or clauses comma use, 44, 116–117 grammar overview, 109 writing style, 44 Results integrity issues, See Ethics entries “Results” section in scientiﬁc papers, 7, 23 Review articles description, 19 standard format, 20, 21 Reviewers of manuscripts anonymity of, 8, 71–72 author requests regarding, 13, 72, 75 editorial process, 29, 31, 32 electronic submission of manuscripts, 60, 63, 68 ethical considerations, 5, 8–9 ethical guidelines, 15–16, 73, 74, 76 peer-review process, 72–73 responsibilities of, 73–74 selection of, 15, 72–73, 75 See also Peer review Revising your manuscript, 31, 32b, 63–64, 75–76 RGB color mode, 350, 352, 362 Ribonucleic acid, abbreviations, 244t Rich Site Summary (RSS), 100 Ring size, structure preparation, 378 RNA, abbreviations, 244t Roman numerals vs arabic, 206, 369, 375–378 chemical structure identiﬁcation, 376–377 for oxidation numbers, 262 Roman type in abbreviations and symbols, 154–155, 159–160, 212–213, 216, 241, 271–272 for chemical compounds, 259 for chemical element symbols, 159, 234, 241 combinatorial chemistry representation, 246 for electronic conﬁguration, 256 in ﬁgures, 356b in locants and descriptors, 234 in mathematical copy, 212–213, 214, 223 for phenotypes, 154 for polymer names, 242 references to books, 301–304, 306 references to meetings and conferences, 308–309 references to periodicals, 291, 297–299 references to theses, 309 references to U.S. government publications, 312 for restriction endonucleases, 155 in subscripts or superscripts, 216 superatom representation, 246 for syllabic portion of chemical names, 233, 240 for trigonometric and other functions, 219, 220 See also Boldface type, Italic type Rotation crystallographic point groups, 269 optical, 270 speciﬁc, 274 RSS (RDF Site Summary or Rich Site Summary), 100 Rules, straddle, 371, 372t S- vs S-, when to italicize, 235 S and S∗ preﬁxes in chemical names, 236, 270 s orbitals for polymer bead representation, 251 Saccharides, abbreviations, 243t–244 Safety information, See Chemical safety information Scalar, mathematical concept, 210 Scalar variables, single-letter, 215 Scaling of artwork, See Proportionality in artwork, Sizing of artwork Scanning programs, 350–352, 355b Scanning tips for ﬁgures, 353b, 354, 355b, 360, 362 Scatter plots, 347 Scheduling concerns, See Timeliness as issue Index Schemas in CML, 95, 96 in XML, 90–91, 96, 98, 99 “Scheme”, capitalization, 143 Schemes in abstracts, 22 citing, 143 CML example, 93s in combinatorial chemistry, 246, 251–252, 252f deﬁnition, 376 editorial process, 29 footnotes, 378 numbering, 206, 346, 378 preparing, 379 titles, 148, 378 types of artwork, 347 when to use, 376, 377f XML example, 91s See also Chemical reactions Schoenﬂies symbols, crystallography, 269 ScholarOne, editorial systems, 60, 69t Scientiﬁc and technical information exchange (STIX) fonts, 357b Scientiﬁc method, relation to format of scientiﬁc paper, 19 Scientiﬁc notation, 207, 209–210 Scientiﬁc papers (in general) book categories, 17–18 ﬁgure use, 343, 344 journal presentations, 18–19 standard format, 19–26, 28 structure use, 375 table use, 369 word choice, 50 Scientiﬁc publication, ethics in, See Ethical guidelines, Ethics in scientiﬁc publication Scientiﬁc publishers, See Publisher entries Scientiﬁc search services, 72 Scientiﬁc vs other writing styles, 16, 28, 50 SciFinder (search service), 72, 254 SciFinder Scholar (search service), 72 Screening (printing process), 347, 362, 363 Script letters, 214 Search engines, Web-based, 99, 383 Search services, 72, 254 Seasons, capitalization, 148 Second person as gender-neutral alternative, 58 Seconds symbol, spacing, 203, 224 “Section”, capitalization, 144 Semantic web concept, 89, 96 See also Datuments Semantics, in markup languages, 93–94, 96–99 Semicolon between independent clauses, 119–120 reference citation guidelines, 289 ➤ 421 Semicolon—continued references to books, 301–305 references to meetings and conferences, 308–309 references to patents, 310 references to periodicals, 291, 297–299 references to U.S. government publications, 312–313 with series items, 119 Semiotics, deﬁnition, 98 Sentence modiﬁers, 44–45, 109–113 Sentence structure comparisons, 48–50 parallelism, 46–48, 50 sentence modiﬁers, 44–45, 109–113 split inﬁnitives, 43 subject–verb agreement, 43–44, 105–108 verb omissions, 108 verb tenses, 42–43 voice, 42 word order, 45–46 “Separately”, 55 Sequences, nucleotide, 244 Sequential numbering, See Numbering Serial comma, 114, 115, 119 Serial data sets, 314–315 Serial unit modiﬁers with same base, 141 “Series” as CASSI keyword, 306 as collective noun, 306 Series items comma use, 114, 115, 119 ellipses use, 127 en dash use, 209 enumerations, 123, 206–207 numeral and word usage, 123, 127, 204, 206–207, 209 parallelism, 48 semicolon use, 119 units of measure as ﬁnal item, 226 Series publications, reference format, 292t, 304, 305–306 Series titles, 20, 305–306 Service mark symbol, 157 Set notation, 222 “Several”, subject–verb agreement, 108 Sexist language, avoiding, 57–58 SGML (Standard Generalized Markup Language), 90 Shades of gray, types of artwork, 347 Shading in artwork, 345b, 347, 359f, 363 Shareware, public domain status, 81 SI-derived units, 229t, 230t SI units atomic and molecular, 277 base units, 228, 229t 422 ➤ The ACS Style Guide SI units—continued capitalization, 228 chemical kinetics, 277–278 electricity and magnetism, 278–279 electrochemistry, 279 general chemistry, 279–280 mechanics, 280 multiplying preﬁxes, 229t NMR spectroscopy, 281 polymer chemistry, 281 radiation, 282 space and time, 282 supplementary units, 228, 229t system background, 228 technical documents usage, 223 thermodynamics, 283 transport properties, 283 Signiﬁcance of results as publication issue, 4–5 “Similar to” in comparisons, 49 Simple past tense, 43 Simple sentences, deﬁnition, 42 Simultaneous manuscript submissions, 5, 14, 16 “Since”, usage guidelines, 46 Single-crystal analysis, CIF format requirement, 284 Single letters or numbers in unit modiﬁers, 142, 143 Sizing of artwork, 352–354, 355, 370, 373 Sketches, 347 See also Artwork, Figures, Illustrations Slang, avoiding, 54 Slash between components of mixture, 121, 126, 222, 261 with compound units of measure, 224, 226 for division, 220, 224 misuse for “and” or “or”, 56 in ratios, 121, 222 spacing considerations, 215, 217, 219–220 and spelled-out units of measure, 225, 226 and units of measure in tables, 371 in Web addresses, 156 Small capital letters in chemical names, 233, 236, 238t, 245, 270–271 Small-molecule crystal structures, data sources, 284 SMILES identiﬁers, 94 “So” as coordinating conjunction, 47, 113, 149 Software processing of data, See Databases, Datuments Software programs capitalization, 156 and CIF format, 285–286 citation management, 326–327 cited as references, 314, 323–325 combinatorial chemistry representation, 251 Software programs—continued data set citation format, 314 datument potential, 98–99 editorial process, 29, 30 electronic submission of manuscripts, 60, 65t–67t ﬁgure preparation, 343, 346, 350–352, 354, 355b, 363 font copyrights, 357b structure preparation, 375, 378–383 table preparation, 373–374 Web-enhanced object viewing, 25 See also speciﬁc software Solid state, indicating in reactions, 272 Solid supports, in combinatorial chemistry, 251 Solidus, See Slash Soluble supports, in combinatorial chemistry, 251 “Some”, subject–verb agreement, 108 Sound ﬁles, Web-enhanced objects, 25 Source ﬁle formats, See Computer ﬁle formats “Source” line in table footnotes, 373 “sp.”, capitalization, 146 Space and time, symbols and SI units, 282 Space groups, crystallographic, 269–270 Spacing in CASSI abbreviations, 294 with centered dots, 215, 219, 261 in chemical reactions, 272, 379 in citations of standards, 276 with compound units of measure, 224 between curves in ﬁgures, 358 between display fractions, 219 between element and spectral line, 276 with ellipses, 219 with “exp”, 217 around geometric notation, 223 of indices and element names or symbols, 268 mathematical copy guidelines, 210–223 around mathematical functions and operators, 214–215, 217, 219, 222 around mathematical variables, 215 in multiplication, 215, 219, 224 in numbers with ﬁve or more digits, 207–208 in numbers with four digits, 207 between numerals and units, 203, 223–224, 271–272 of oxidation numbers, 262–263 with percent sign, 203, 224, 271 of periods after initials, 119 of position numbers, 246 with ratio colons, 215, 219 reference citation guidelines, 117, 209, 289 Index Spacing—continued references to books, 304 references to periodicals, 296–297 with slashes, 215, 217, 219–220 in standard deviation or standard error, 208–209 Spanish surnames, 153 Spans, See Ranges Special characters, See Greek letters, Symbols Special event names, capitalization, 148 Special materials used in research, distribution of, 8 Special Publication 330, National Institute of Standards, 255 Special sections, standard format, 24–25 Special typefaces, See Boldface type, Italic type Species names abbreviating vs spelling out, 160 capitalization, 146, 150 italic type use, 154 Species numbers, 272 Speciﬁc rotation, reporting analytical data, 274 Spectra, Web-enhanced objects, 25 Spectral characterization data as supporting information, 25 Spectral information, datument potential, 99 Spectroscopy data types and representation, 274–276 symbols and SI units, 281 Speculations, labeling in papers, 7 Speeches, converted to scientiﬁc papers, 57 Spelling ACS desk reference use, 127 company names, 127 computer and Internet terms, 163–168 in direct quotations and titles, 127 plurals, 128 possessives, 127 recommended spelling list, 129–133 Spelling out abbreviations, 158, 160 “equation” in text, 221 fractions, 139 numbers vs numerals, 160, 203–205 taxonomic names, 160 terms in titles, 20 units of measure, 160, 225–226 Spin multiplicity, chemical conventions, 257 Spiro alicyclic compounds, nomenclature, 236 “spiro” preﬁx, style for, 236 Split idioms, 49 Split inﬁnitives, 43 Sponsors, “Acknowledgments” section contents, 24 “spp.”, capitalization, 146 ➤ 423 Square brackets in bridged and spiro alicyclic compound names, 236 with concentrations, 124, 271 with coordination entities, 260 with crystallographic indices, 268 isotopic labeling, 264–265 in mathematical copy, 124, 212, 214–216 in mathematical equations, 219–220 nesting order, 216 for oligosaccharides, 244 in polycyclic aromatic compounds, 240 in polymer or complex chemical names, 151 with quotation marks, 124 references to online sources, 315, 318 with syllabic portion of chemical names, 240 Square roots, radicals vs superscripts, 217 “Sr.” and “Jr.”, 117, 291, 301, 309, 312 Stacking (aligning) subscripts and superscripts, 269 Staggering subscripts and superscripts conventions in chemistry, 269 for ionic charge, 262 mathematical copy preferences, 216 Standard deviation or standard error, numbers style, 208–209 Standard format for scientiﬁc papers abstract, 21–22 acknowledgments, 24 byline and afﬁliation, 21 conclusions, 23 discussion, 23 editorial process, 28, 29 experimental details or theoretical basis, 22–23 introduction, 22 references, 24 results, 23 special sections, 24–25 summary, 24 supporting information, 23, 25 title, 20 Web-enhanced objects, 25–26 Standard Generalized Markup Language (SGML), 90 Standards for chemical symbols and nomenclature, 255 citing in reports, 276 for structure representation, 383 stat inﬁx in copolymer names, 243 State abbreviations with CASSI abbreviations, 294 U.S. Postal Service, 161–162, 303, 310 State and city names for place of publication, 294, 295, 303, 310 424 ➤ The ACS Style Guide State government publications, cited as references, 313–314 Statistical notation, 223 Stereochemical descriptors in chemical names, 235, 236, 239t, 240 and chirality, 270 See also Chemical descriptors, Locants Stereochemical preﬁxes, 235 Stereoisomer descriptors, 145 “Still”, hyphenation in unit modiﬁers, 141 STIX fonts, 357b STM publishing, deﬁnition, 27, 90 STN International, 254 Straddle rules, 371, 372t Structural descriptors, 236, 238t–239t Structural point groups, crystallography, 269 Structural preﬁxes, chemical names, 235–236 Structure data for crystals, See Crystallographic information ﬁles (CIF) Structure numbers in ChemSet notation, 246, 251–252 Structures in abstracts, 22 CAS Chemical Registry Numbers, 253–254 citing, 376–378 in combinatorial chemistry, 246, 250–252 description, 375 editorial process, 29 font selection, 380 freeware for drawing, 379–381 future of representation, 382–383 grouped in charts, 376, 379 as illustrations, 273 InChI identiﬁers, 101–102, 383 numbering, 206, 246, 346, 375–377 organic group abbreviations, 260 preparing, 378–381 submitting, 381–382 in tables, 374, 378 types of artwork, 347 unique label possibility, 383 Web-enhanced objects, 25 when to use, 375–376, 377f See also Artwork, Illustrations Stub in tables, 371, 372t Student t test, 223 Subatomic particles, chemical conventions, 256 Subheadings capitalization, 148 parallelism, 48 Subject–verb agreement, 43–44, 105–108 Submission of manuscripts, See Electronic submission of manuscripts, Manuscript processing stages Submitted materials in reference lists, 315–316 Submitting agents, 62 Subordinate clauses comma use, 114 deﬁnition, 42 as sentence modiﬁers, 113 Subordinating conjunctions comma use, 116 in comparisons, 48 in titles and headings, 150 writing style, 46 Subscripts for atomic numbers, 262 in Boughton system for isotopes, 265–266 with chemical reactions, 273 for electronic conﬁguration, 257 fractions in, 217 “index” deﬁnition, 211 for ionic charge, 262 italic vs roman type, 216 in mathematical copy, 160, 215–217 mathematical expressions in, 217 in mathematical symbols, 211 for number of atoms, 263 for orbital axes, 256 plurals of abbreviations ending in, 161 spacing around operators, 215, 219 staggering and stacking with superscripts, 216, 262, 269 in superatom designations, 246, 251 in titles, 20 Subspecies names capitalization, 146 italic type use, 154 Substituents, in combinatorial chemistry, 246, 250 Substitution, isotopic, 264–266 Subtitles, capitalization, 148 “Such as”, restrictive and nonrestrictive uses, 116 Sufﬁxes hyphenation, 137–138, 150, 152, 247–249 to proper nouns and adjectives, 152 subject–verb agreement, 107 Sugars nucleic acid abbreviations, 244t saccharide abbreviations, 243t, 244 Summaries, scientiﬁc paper format, 24 See also Abstracts “Sun”, capitalization, 148 Superatoms, designation, 246, 250–251 Superlatives, hyphenation in unit modiﬁers, 141 Superscripts with chemical reactions, 274 for corresponding author information, 21 for electric charge indicators, 256 Index Superscripts—continued for electronic conﬁguration, 256–257 fractions in, 217 “index” deﬁnition, 211 for ionic charge, 262, 266 italic vs roman type, 216, 373 for mass number, 261, 263 in mathematical copy, 160, 215–217 mathematical expressions in, 217 in mathematical symbols, 211 misuse in isotopic labeling, 265 for oxidation numbers, 262–263 plurals of abbreviations ending in, 161 vs radical signs, 217 reference citation guidelines, 30, 117, 209, 287 references to periodicals, 298 spacing around operators, 215, 219 staggering and stacking with subscripts, 216, 262, 269 in table footnotes, 373 in titles, 20 Supplements, reference format, 296 Supporting information datument potential, 98–99 datument validation, 96 electronic submission of manuscripts, 63, 69t, 382b ethical considerations, 5 for lengthy derivations, 23 manuscript revisions, 32b standard format, 23, 25 Supports, in combinatorial chemistry, 251 Surnames byline format, 21 capitalization, 151–152, 153, 225 foreign, 139, 152–153 hyphenation, 139, 152–153 as modiﬁers, 151 reference collation, 290, 325–326 reference format, 153, 291, 301, 309, 312 as units of measure, 151–152, 225 See also Author names in references, Author names in text, Personal names Syllabic portion of chemical names, 233, 240, 241 Symbols atomic and molecular symbols, 277 capitalization guidelines, 145 case sensitivity, 159 chemical kinetics symbols, 277–278 in chemical reactions, 272 commonly used in chemistry, 169–202 crystallography symbols, 269 electricity and magnetism symbols, 278–279 electrochemistry symbols, 279 ➤ 425 Symbols—continued en dash use, 125, 209 in ﬁgures, 353b, 356, 358f, 363, 365 font availability, 365 general chemistry symbols, 279–280 for isotopes, 264–266 isotopic labeling, 264–266 mathematical notation, 222–223 mechanics symbols, 280 NMR spectroscopy symbols, 281 for non-SI units, 231t nonmathematical symbols, 212 for physical quantities, 277–283 polymer chemistry symbols, 281 for positions of atoms, 263 radiation symbols, 282 reporting analytical data, 274 Schoenﬂies, 269 for SI-derived units, 229t, 230t for SI units, 229t sizing of, 353b, 356 space and time symbols, 282 spacing guidelines, 203 in tables, 370, 371, 373, 374 thermodynamics symbols, 283 in titles, 20 for trademarks, 23, 157 transport properties symbols, 283 See also Abbreviations, Acronyms, Chemical symbols, Element symbols, Mathematical symbols, speciﬁc symbols Symmetry operations, crystallography, 269 Symmetry site terms and chirality, 270 Symposia, See Meeting and conference presentations “Syn”, italicization and capitalization, 145 Synonymous terms, word choice considerations, 50 Syntax and CIF format, 286 Synthesis, combinatorial, See Combinatorial chemistry Systematic chemical names, 22 Système International d’Unités, See SI units t test, 223 Tab key, avoiding in table preparation, 373 “Table”, capitalization, 143, 369 Table feature of software, 373–374 Tables abbreviation use, 160, 225, 370, 371, 372, 373 abstract guidelines, 22 adapted, 84b, 366 citing, 143, 369–370 column entry guidelines, 207, 371–374 column heading guidelines, 225, 371, 372t 426 ➤ The ACS Style Guide Tables—continued column width guidelines, 370 editorial process, 29–30, 33 “Experimental” section contents, 23 footnotes, 371, 372–373 formal vs informal, 370, 374 vs lists, 370, 374 numbering, 206, 369 parallelism, 48, 371 parts of, 371, 372t permission requirements, 83–86, 366 preparing, 370–374 references in, 289, 373 repeated entries, 372 row heading guidelines, 371 section heading guidelines, 48 section widths, 371 sizing, 370, 373 standard deviations or standard errors, 209 structures in, 374, 378 submitting, 374 as supporting information, 25 symbol use, 370, 371, 373, 374 titles, 148, 371, 372t typesetting cost, 370 unit of measure guidelines, 207, 225, 371, 373 when to use, 344b, 369, 370 word-processing software use, 373–374 See also Artwork Tagged Image File Format, See TIFF format Tags, markup described, 89 HTML limitations, 90 “tag soup” problem, 93 See also Datuments “Taking” as sentence modiﬁer, 112 Tangible medium of expression, deﬁnition, 77 Tarred ﬁles, 62 Taxonomic terms abbreviating vs spelling out, 160 capitalization, 145–146, 150 italic type use, 155, 160 Technical editing datument potential, 98–99 editing services, 75 reference accuracy, 30 role, 33 See also Editorial process, Editors Technical reports and bulletins, reference format, 292t, 314, 324 Television commercials, still shot permissions, 83 Telnet sites, cited as reference, 320 Temperature, units of, See Units of temperature Temperature scale names, capitalization, 225 Templates editorial process, 29 electronic submission of manuscripts, 60 reference management programs, 326–327 standard format, 20 structure preparation, 380–381 Temple Peer Review Manager (software), 60 Tenses, 42–43 Tensors boldface type for tensors, 213 deﬁnition, 210 italic type for components, 212 Territory abbreviations, 161–162 TeX (software), 61 Text editors and CIF format, 286 Text ﬁle formats, See Computer ﬁle formats Text settings for ACS publications, 381b Thai surnames, 153 “Than” in comparisons, 48 “That” antecedent clarity, 46 with restrictive clauses, 109 “That is”, 117, 160 “The” before collective nouns, 106 as gender-neutral alternative, 58 in journal names, 294 in titles, 20, 149, 154 Theoretical papers, standard format, 20, 23 Thermodynamics, symbols and SI units, 283 Theses, cited as reference, 292t, 309–310, 321, 325 “This”, antecedent clarity, 46 Thomson Scientiﬁc products, 327 Three-dimensional art, structure preparation, 378 “Through”, vs en dash, 125, 209 Tick marks in ﬁgures, 353b TIFF format, 61, 351–352, 353b, 357b, 363, 381, 382b Tilde (~) for polyatomic molecules, 257 Time, units of, See Units of time Time and space, symbols and SI units, 282 Timeliness as issue ASAP articles, 34, 318–319 for authors, 4–5, 75 checking proofs, 33, 34 datument potential, 99 for editors, 12 and full disclosure, 5–6 and nonstandard formats, 20 for peer reviewers, 9, 16, 73 permission requests, 30, 84–86 and signiﬁcance of results, 4–5 and word choice, 57 “Times”, nonmathematical sense, 205 Index Times New Roman typeface, 357b Times Roman typeface, 356b, 363 Times sign (×), use guidelines, 215 Titles (in references), See Article titles in periodical citations, Book titles, Chapter titles, Journal titles Titles (in text) abbreviation guidelines, 20, 150, 159, 160 artwork guidelines, 371, 377, 378 capitalization, 148–151, 227, 237t–239t quotation marks use, 122 spelling recommendations, 127 standard format, 20 trademarks not used in, 157 unnumbered lists in manuscripts, 374 Titles (professional or personal) in bylines, 21 capitalization, 147–148 foreign surnames, 152 “To” capitalization in inﬁnitives, 149 vs en dash, 124–125, 209 “To be” verb forms, 51, 111, 143 Toner cartridges for ﬁgure artwork, 353b, 360 Top-level elements (markup language component), 91 “torr” vs “Torr”, 225 Toxic Substances Control Act Inventory, 254 Trade names vs generic names, 157 Trademark symbol, 23, 157 Trademarks capitalization, 146, 157 deﬁnition, 157 scientiﬁc paper format, 23 in titles, 20 use guidelines, 157 “Trans”, italicization and capitalization, 145, 150 Transcripts of speeches, 57 Transfer of copyright, 32, 33, 78, 82, 86 Transitional phrases comma use, 117 semicolon use, 119–120 Translations, citation formats, 299 Transliteration of foreign names, 153 Transport properties, 212, 215, 283 Transposes of matrices, 213 Tree view of markup languages, 94, 95f “tri” in element names, 260 Tricky possessives and plurals, 127–128 Trigonometric and other functions line breaks, 220 roman type use, 213, 220 spacing considerations, 213 Trim size for ACS books, 354t Triple bonds in chemical formulas, 267 Tritium, representation, 264, 266 ➤ 427 Trivial chemical names, 22 TrueType font format, 357b Truncation in e-mail addresses, 157 Two-letter initials, foreign names, 153 Two-letter variables, italic type use, 212 Two-word compounds, hyphenation, 137, 138 See also Compound words Two-word concepts, en dash use, 124–125 Two-word verbs, hyphenation, 139 Type and photograph combinations, See Combos (artwork) Type size chemical reactions, 272 ﬁgures, 353b, 356b, 357b, 358f, 360, 365 structures, 378 tables, 373 Type weight, deﬁnition and examples, 356b Typefaces, See Boldface type, Fonts, Italic type, Roman type U for uniform labeling, 265 “U.K.” in references, 294, 303, 310 when to abbreviate, 161 Undergraduate students and peer review, 9, 75 Underscore in e-mail addresses, 157 Unhyphenated preﬁxes, 135–136 Uniform resource identiﬁer (URI), 92 Uniform resource locator (URL) in Internet reference citations, 315, 317–320 line break guidelines, 156 persistent URLs, 317 WWW address format, 156 WWW history, 89 See also World Wide Web sites Unit cells, crystallographic types, 269 Unit modiﬁers capitalization in titles and headings, 150, 225, 227 deﬁnition and types of, 139–140 editorial list, 140 foreign phrases as, 139 hyphenation, 138, 139–143 phrasal verbs as, 139 as predicate adjectives, 143 serial, with same ending base, 141 three or more words, 142–143 Unit of measure–number combination as singular, 51 United Kingdom in references, 294, 303, 310 when to abbreviate, 161 United States commercial chemical inventories, 254 when to abbreviate, 161 See also U.S. entries 428 ➤ The ACS Style Guide Units of measure abbreviating vs spelling out, 160, 225–226 axis labels on illustrations, 359 capitalization, 150, 225, 227 case sensitivity, 159 as collective nouns, 107 comparison words, 51 compound, 224, 226, 230t decimals use, 208 deﬁnition not required, 224 discipline-speciﬁc preferences, 207 hyphenation of unit modiﬁers, 141–143 large numbers with, 207 non-SI units list, 231t, 232t not having abbreviations, 225 numeral and word usage, 203, 204 period use, 118, 223 plural forms, 224, 225 in ranges and series, 226 roman type use, 212 spacing, 203, 223–224, 271–272 spelling out, 160, 225–226 surnames as, 151–152, 225 systems overview, 228 in tables, 207, 225, 371, 373 usage overview, 223–227 See also SI units Units of temperature capitalization, 225 degree symbol guidelines, 203, 208, 224, 227 non-SI units lists, 231t SI units list, 229t Units of time decimals use, 208 hyphenation of unit modiﬁers, 141 minute and second symbol spacing, 203, 224 month abbreviations, 160–161 non-SI units lists, 231t numeral and word usage, 160, 203, 205 roman type use, 212 seasons capitalization, 149 SI units list, 229t University name and location in thesis citation, 310 Unknown quantities deﬁning symbols in text, 211 italic type use, 212 Unnamed chemical elements, 260 Unprimed numbering, 244 Unpublished materials ethical obligations authors, 7 editors, 12–13 reviewers, 9, 16 reference format, 308–309, 315–316, 322 URI (uniform resource identiﬁer), 92 URL, See Uniform resource locator “U.S.” in references, 294 when to abbreviate, 161 U.S. Code, cited as reference, 313 U.S. Copyright Ofﬁce, 79–80, 82 U.S. Department of Health and Human Services, Ofﬁce of Research Integrity, 4 U.S. government authorship, ACS copyright policy, 81 U.S. Government Printing Ofﬁce, 311, 312 U.S. government publications cited as references, 292t, 295, 311–313, 321 Code of Federal Regulations, 313 copyright, 81, 366 Federal Register, 313 U.S. Code, 313 U.S. laws, 313 U.S. laws, cited as reference, 313 U.S. monetary values, 208 U.S. National Institute of Standards and Technology, 101 U.S. patents cited as reference, 292t, 310–311 style guidelines, 208 U.S. Postal Service abbreviations, 161–162, 303, 310 U.S. regulatory agencies, 254 “U.S.A.”, CASSI spacing exception, 294 Usage of words, See Word usage User names for author home pages, 62 Uuencoded ﬁles, 62 UV–visible spectroscopy, reporting analytical data, 276 Valence conﬁgurations, 256 Validation of datuments, 96–97 Validation reports for CIF compliance, 63, 286 “Values” with plurals of symbols, 211 Vanadium symbol, avoiding confusion with numerals, 262 Variables in combinatorial chemistry, 246, 250 deﬁning, 211, 225, 371 Greek letter use, 214 italic type use, 212 as mathematical concept, 210 roman type use, 213 spacing between, 215, 219 Variety names capitalization, 146 italic type use, 154 “Variety of ” as collective noun, 106 Vectors boldface type for vectors, 213 Greek letter use, 214 Index Vectors—continued italic type for components, 212 as mathematical concept, 210 Verb–subject agreement, 43–44, 105–108 Verb tenses, 42–43 Verbs, phrasal, 139, 150 Verbs, two-word, 139 “Versus”, 50, 124–125, 160 Video still shot permissions, 83 Web-enhanced objects, 25, 26 Vietnamese surnames, 153 Vocabularies, controlled, 97–98 Voice, See Active voice, Passive voice “Vols.” vs “vols.” in book citations, 304 Volume number books, 303–304, 306 meetings and conferences, 308 periodicals, 295, 296, 297–298 “vs”, 160 Water of hydration, centered dot use, 261 “We”, writing style, 43–44 Web-based applets for drawing, 379 Web-based publications caption preparation, 365 font tips, 357b illustration preparation, 344, 346, 350–352 reference accuracy, 24, 30, 31 supporting information, 25 See also Electronic source citation, Online books, Online periodicals Web-based search engines, 99, 383 Web-based systems manuscript submission via, 31, 32, 59–69 permission requests via, 83–84 proof return via, 34b reference management programs, 326–327 supporting information on, 5, 25 Web browsers electronic submission of manuscripts, 61, 68 markup language display, 94 markup languages and the WWW, 90 Web-enhanced objects (WEOs), 25–26 Web sites, See World Wide Web sites WebLab Viewer (helper application), 25 Webster’s New World College Dictionary, 127, 135 Webster’s Third New International Dictionary, 127, 135 “Well”, hyphenation in unit modiﬁers, 141 When to publish, See Timeliness as issue “Whereas”, usage guidelines, 46 “Whether” vs “Whether or not”, 52–53 “Which”, with nonrestrictive clauses, 109 “While”, usage guidelines, 46 ➤ 429 “Who”, with nonrestrictive clauses, 109 “wide”, hyphenation as sufﬁx, 138 “Wife”, gender-neutral alternatives, 58 Windows platform reference manager programs for, 327 templates for, 29 “With”, alternatives to, 56 Word (software), 61, 352, 363, 373, 379 Word choice, See Word usage Word deﬁnitions, italic type use, 154 Word omissions in comparisons, 48–49 verbs and auxiliary verbs, 108 Word order in comparisons, 48–49 sentence construction, 45–46 Word-processing ﬁle formats, See Computer ﬁle formats Word-processing software electronic submission of manuscripts, 61 ﬁgure preparation, 352, 363 reference management programs, 326 structure preparation, 379 table preparation, 373–374 Word-processing templates, See Templates Word spacing, See Spacing Word usage in captions, 365 confusable words and phrases, 51–53, 111–112 gender-neutral language, 57–58 grouping and comparison words, 50–51 and manuscript revisions, 32b numeral and word usage, 160, 203–207 in scientiﬁc vs other writing, 16, 28, 50 in titles, 20 units of measure guidelines, 223–227 words and phrases to avoid, 54–57 Wordiness in article titles, 20 examples, 54–55 WordPerfect (software), 61, 352, 363, 373 Works made for hire and copyright, 78, 82 World Wide Web and markup languages, 89–96 URL forms, 156 World Wide Web sites ACS author guidelines, 29, 343, 381b ACS ethical guidelines, 11 ACS permission requests, 83 ACS publication home pages, 28b ACS Publications Division, 86 ASAP articles, 34 author guidelines on, 75 Cambridge Crystallographic Data Centre, 284, 286 430 ➤ The ACS Style Guide World Wide Web sites—continued Chemical Abstracts Service, 253 citation of Internet sources, 293t, 314, 320–321 company sites, 127 computer and Internet terms on, 163–168 copyright issues, 79, 81, 82, 83 CRYSTMET database, 284 data set citation format, 314 DOI system, 317 drawing software resources on, 380, 380b Dublin Core Schema, 90 electronic submission of manuscripts via, 60, 65t–67t graphics resolution on, 364 ICSD database, 284 International Organization for Standardization, 255 International Union of Crystallography, 284, 286 International Union of Pure and Applied Chemistry, 97, 102, 255, 383 molﬁle format information on, 381 National Academy of Sciences, 4 National Institute of Standards and Technology, 228, 255 Nucleic Acid Database, 284 Ofﬁce of Research Integrity, 4 Organic Syntheses, 305 peer-review information, 71 Protein Data Bank, 284 STIX font downloads on, 357b structure representation standards on, 383 supporting information on, 25 templates on, 29 XML-related information, 90 Writing process, getting started, 27–28 Writing style scientiﬁc vs other styles, 16, 28, 50 sentence structure guidelines, 41–50, 105–113 Writing style—continued usage guidelines, 50–58, 111–112, 160, 203–207, 223–227 See also speciﬁc aspects WWW, See World Wide Web entries X for products mixed, 246, 251, 252 “X-ray”, capitalization, 144, 149 X-ray diffraction spectroscopy, reporting analytical data, 276 XML (extensible markup language) datument as scientiﬁc grid component, 99 datument potential, 99 datument validation, 96 datument vocabularies, 98 display of, 94–96 examples of, 90–94, 91s WWW history, 90 XML Query protocol, 99 Xpress Track (software), 60 XSL (extensible stylesheet language), 90 XSLT technology, 94 Year of publication books, 303 editorial process overview, 30 periodicals, 296, 297–298 theses, 310 U.S. government publications, 312 See also Author–date citations “Yet” as coordinating conjunction, 47, 113, 149 Z preﬁx in chemical names, 236 Zero before decimal point, 208 as electric charge indicator, 256 Zipped ﬁles, 62 Zones, crystallographic notation, 268

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