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Glossary of Terms Used in Physical Organic Chemistry

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Glossary of Terms Used in Physical Organic Chemistry PUre & AppL. Chem,, Vol. 51, pp. 1725-1801. 0033-4545/79/0801-1725 $02.00/0 Pergamon Press Ltd. 1979. Printed in Great Britain. ©IUPAC PROVISIONAL INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY ORGANIC CHEMISTRY DIVISION COMMISSION ON PHYSICAL ORGANIC CHEMISTRY* GLOSSARY OF TERMS USED IN PHYSICAL ORGANIC CHEMISTRY Compiled and Edited by VICTOR GOLD Comments on these proposals should be sent within 8 months of Publication to the S=etary of the Commission: Dr. J. R. PENTON Technisch-Chenmches Laboratorium der EidgenOssischen Technischen Hochschule Zürich Universitlltstrasse 6 CH-8092 Zürich, Switzerland Comments from the viewpoint of languages other than English are encouraged. These may have special significance regarding the eventual publication in various countries of translations of the nomenclature finally approved by IUPAC. *The mernbership of the Commission during the period in which this Glossary was prepared was as follows: J. F. DUNNETT (Titular Mernber, 1973-79; Chairman, 1978-; USA) A. R. H. COLE (Associate Member, 1974-79; Australia) V. GOLD (Titular Mernber, 1973·79; UK) R. D. GUTHRJE (Associate Mernber, 1977-81; USA) G.ILLUMINATI (Titular Mernber, 1977-81; ltaly) R. A. Y. JONES(AssociateMernber,l977-81; UK) J. MARCH(AssociateMernber,1977-81; USA) J. R. PENTON (Titular Mernber and Secretary, 1973·79; Switzerland) M. J. PERKINS (Titular Mernber, 1977-81; UK) J. REEDIJK (AssociateMernber,1977-81; Netherlands) C. RÜCHARDT (Titular Mernber, 1973-77; Federal Republic ofGermany) K. SCHWETLICK (Titular Mernber, 1977-81; German Dernocratic Republic) A. STREITWIESER(Titular Member, 1973-77; Associate Mernber, 1977-81; USA) J. TOUL!,l!C (TitularMernber,l973-79; France) H. ZOLLINGER (Titular Mernber, 1973-79; Chairman, 1973-78; Switzerland) CONTRIBUTORS TO THE GLOSSARY w. J. Albery V. Gold R. M. Noyes R. w. Al der D. G. Gorenstein G. A. Olah E. M. Arnett F. D. Greene J. R. Penton M. Back E. Grunwald M. J. Perkins P. J. Baldry E. A. Halevi c. L. Perrin A. J. Bellamy R. A. Hancock A. Pross M. L. Bender E. Havinga R. A. Raphael T. w. Bentley A. F. Hegarty A. Rassat c. F. Bernasconi F. Hibbert J. Reedijk L. F. Bertello K. N. Houk w. G. Richards D. Bethell R. Huisgen J. H. Ridd M. J. Blandamer c. D. Hurd c. D. Ritchie E. Buncel G. Illuminati M. J. T. Robinson J. F. Bunnett K. u. Ingold I. H. Sadler D. H. Busch R. A. Jackson o. Samuelson A. R. Butler w. P. Jencks D. P. N. Satchell J. I. G. Cadogan J. L. Jensen w. H. Saunders E. F. Caldin R. A. Y. Jones K. Schaffner B. Capon s. P. Klesney P. von R. Schleyer R. E. Carter J. K. Kochi K. Schofield B. c. Challis G. Köhnstam K. Schwetlick M. Charton G. M. Kramer G. Scorrano P. A. Claret M. M. Kreevoy s. Seltzer J. Cornelisse K. J. Laidler H. J. Shine D. J. Cram J. E. Leonard J. Shorter M. R. Crampton D. R. Lide M. Simonyi L. c. Cross M. Liler P. A. s. Smith A. J. B. Cruickshank J. s. Littler c. J. M. Stirling A. G. Davies K.-T. Liu A. streitwieser E. T. Denisov J. s. Lomas A. Thomas D. F. DeTar A. Maccoll J. Toullec M. J. s. Dewar D. J. McLennan c. Walling M. P. Doyle A. D. McNaught B. M. Wepster w. Drenth R. Mcweeny E. Whalley L. Eberson J. March D. H. Whiffen D. G. Farnum R. A. Marcus M. c. Whiting A. Fava H. Maskill c. F. Wilcox J. H. Fendler L. Melander M. Wolfsberg c. Fernelius s. I. Miller K. Yamasaki R. Foster B. Milligan P. Yates J. F. Garst G. Modena Y. Yukawa· G. B. Gill R. A. More O'Ferrall H. Zollinger E. w. Godly R. 0. c. Norman Editorial help has been given by Miss L. A. Dinsdale. The typescript (in camera-ready form) was prepared by Miss Kathleen Harris. GLOSSARY OF TERMS USED IN PHYSICAL ORGANIC CHEMISTRY INTRODUCTION At its first set of rneetings, in September 1976, the recently constituted IUPAC Cornrnission III.2 (Physical Organic Chernistry) initiated a project an the definition of terrns used in Physical Organic Chernistry. It was noted that the forrnulation of novel scientific concepts was often arbitrary and unclear, and that scientific cornrnunication between physical organic chernists had been harnpered by disagreernent an the rneaning of irnportant terrns. It was agreed that the progress of the subject could be helped by the cornpilation of a glossary of terrns with the cooperation of active research workers, authors, and teachers of the subjec~ With the help of an international group of ca. 30 original contributors a first draft of the glossary was cornpiled in May 1977 and was distributed to 120 chernists for cornrnent. These cornrnents were incorporated into a secend draft (July 1977) which was considered at the secend group of rneetings of the Cornrnission, in August 1977, when it was approved that I should refer sorne difficult and inconsistent sets of definitions to srnall authoritative working groups, again operating by correspondence. The expansion of sorne of the entries by the inclu­ sion of clarifying exarnples was also recornrnended. The resulting third draft, cornpleted in March 1978, was sent for cornrnent to ca. 150 chernists, including a high proportion of experts working in fields other than Physical Organic Chernistry. It was also distributed to the ca. 250 participants of the 4th Inter­ national Conference an Physical Organic Chernistry in September 1978 and discussed during one of the plenary sessions. The Commission considered outstanding policy questions at its rneeting during the sarne period. The responses received, both oral and written, tagether with provisional cornrnents of IUPAC Cornrnissions II.2 (Nornenclature of Inorganic Chernistry) and III.3 (Organic Photochernistry), and individual comments of rnernbers of Cornrnission III.l (Nornen­ clature of Organic Chernistry) and of the Sub-Committee an Nornenclature and Syrnbolisrn in Chernical Kinetics of Commission I.l (Physicochernical Symbols, Terminology, and Units) were full.y taken into account in the preparation of the final draft. The narnes of the rnany people who have so generously helped, either by the forrnulation of draft definitions or by constructive criticisrn, are listed an a following page. However, inclusion in this list should not be taken as an individual's endorsernent of the glossary or responsibility for its rernaining flaws. Apologies are affered in advance for any inadvertent ornission of the narnes of contributors. The following criteria were adopted for the inclusion of a terrn, but it is inevitable that their application rnay be found to be sornewhat subjective: 1. A term rnust be in current use by several independent authors or have been in such.use until recently. 2. There rnust be sorne arnbiguity or uncertainty in its usage by physical organic chernists or fairly widespread ignorance of its rneaning. Alternatively, its specialist usage in Physical Organic Chernistry rnust significantly differ frorn the generally accepted defin~ions givenin non·scientific dictionaries, or in standard chernistry text-books, or be inadequately dealt with in terrninology reports of other IUPAC commissions. The rnost relevant of these reports are cited in the bibliography at the end of the glossary; their contents are intended to be cornplernented (and not repeated) by the present glossary. The airn of the glossary is to provide guidance an physical-organic chernical termi­ nology with a view to achieving a far-reaching consensus an the definition of useful terrns and the abandonrnent of unsatisfactory or redundant ones. The Commission is anxious to ernphasize that it cannot (and would not wish to) irnpose rules or restrictions, which rnight hinder rather than help the precise forrnulation of new ideas. Where the proper definition of other concepts required it, we have, sparingly and with due hesitation, introduced a few new terms, in the hope that they will gain acceptance an their rnerit. Attention is accord­ ingly drawn to the entries chernical species, rnolecular entity, chernical flux and primitive change. 1727 1728 COMMISSION ON PHYSICAL ORGANIC CHEMISTRY As a matter of policy,,named reactions (such as Diels-Alder) and symbolic represen­ tations of mechanisms (SNl' etc.) have been excluded. These topics are currently under consideration by other working parties of the Commission. Generally speaking, operational definitions were preferred to definitions couched in terms of theoretical models. We have tried to avoid taking sides on issues of scientific, as distinct from semantic, disagreement. Similarly, we hope not to have incorrectly attributed named equations. With this kind of danger in mind, we have only sparingly inserted references to individual authors, either to indicate the origin of a term or to direct attention to a helpful, more elaborate discussion of a concept. It was felt justi­ fiable to exclude named equations and effects that, at the time of compilation of this edition of the Glossary, would not normally be found in the literature without a source reference. A dagger (t) against the title of an entry implies that we recommend discontinuation of its use. The arrangement of entries is simply alphabetical. Underlined words in the body of a definition, as well as those cited at the end, point to relevant cross-references1 double underlining implies that the cross-reference is of special importance to the entry in which it occurs. The appearance of a term in quotation marks in the body of a definition indicates that no further information will be found under that heading. A list of symbols used in the Glossary (and not explicitly defined each time they occur) is provided. With a progressively evolving subject it is, of course, impossible to produce a set of definitions of indefinitely lasting validity. The revision of this Glossary of terms is therefore expected to remain a continuing responsibility of the Commission.
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