J. E. H. Hancock Reed College Portland, Oregon 97202
An Introduction to the Literature of Organic Chemistry Part I: Classes 7-12
Anyone who attempts to write about the organic chemical literature in a journal article runs the risk of being either too ambitious and perhaps tiresomely longwinded, or too limited and therefore superficial. The present paper attempts to steer a middle course and is intended to give some guidelines to the newcomer faced with the necessity of tracking down information. The coverage is meant to be representative rather than comprehensive, and the subject matter is restricted to pure organic chemistry rather than applied. The subject appean to have been last dealt with in THIS JOURNAL in 1944 by Hennion in a three-page article (1). Unfortunately, most of the advice found there is now out of date because of increased publication activity since that time. Many journal articles which have been written on the subject are rather limited in scope; such articles are not particularly useful nowadays, however, since the number of publications has increased tremendously. In addition, the increased role which research plays in today's curricula has necessitated the strengthening of library resources. Further, the increasing importance of photocopying processes has made resource material much more readily available to those who desire it. Although the literature of organic chemistry is still in an evolutionary phase, it would seem useful to provide a survey of its present state as a guide for students. Some of the statistics in this field are startling: since 1750 the number of scientific journals founded and the number of scientists living have doubled every fifteen years. The number of entries in Chemical Abstracts now doubles every eight to twelve years, and the total number of organic compounds now known is about two and a half million, with about eight hundred new ones being added every day (2). It has been estimated that a research chemist needs immediate access to 60&700 relatively common journals, serial publications, and reference works (3). The organic chemical literature is quite well orga-
EDITOR'S NOTE: This is Part I of a three-part article. Part 11, which covers Classes 13-18 and d i s w e s Classes 3 and 4, will appear in April. Part 111, which discusses Classes 5 and 6. will sDDelLr in Mav. The hiblioere~hic style of THIS JOURNALI&been modked slightly Gfit'the intent of the article.
nized. Given a good chemistry library, the practiced student may learn in perhaps an hour or so, depending on the complexity of the pmblem, whether a particular compound has been prepared, and if so a method of synthesis which is probably the preferred one, together with some physical data such as melting point, boiling point, refractive index, and absorption spectra. Several oft-quoted works should be mentioned at the outset, though most of these are not restricted to organic chemistry. Mellon's "Chemical Publications," now in its fourth edition, contains valuable advice on making searches in the chemical literature, a discussion of patent literature, and some library problems (4). It also has a discussion of the organization of all chemical literature from the librarian's point of view (e.g., the Library of Congress and Dewey systems). Dyson has written an admirable little book (5) which contains valuable summaries of information on early journals which have ceased publication. Bottle has edited a series of essays (6) on the chemical literature; this work contains chapters devoted to translations and their sources with special reference to Russian literature, abstracts, abstracting and information retrieval, use of standard tables and handbooks of physical data, and Beilstein, as well as others devoted to miscellaneous aspects of the subject, such as British national libraries. Both Mellon and Bottle give exercises for the student (with hints and answers, respectively), and Dyson gives two complete examples of literature searches of different types-all available data on 4,4'-dimethoxy dibenzyl, and the nitration of hexane. Mellon contains a useful section on nomenclature, though it is mostly restricted to Chemical Abstracts usage; this chapter also contains a valuable discussion of the utility of indexes of all kinds. All of these works pay special attention to the early history of the chemical literature, but that aspect will not come under detailed consideration here. Another book which should be in every library is "A Guide to the Literature of Chemistry," by Crane, Patterson, and Marr (7) ; it contains helpful material on indexes and indexing in addition to many other aspects of the subject. A most valuable source of advice is certain of the volumes of the Advances in Chemistry Series of the American Chemical Society (8); publication no. 30, "Searching the Chemical Literature," is probably the most valuable to the beginner. Volume 45, Number 3, March 1968
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The present analysis of the chemical literature begins with a breakdown into some rather arbitrary classes, listed be lo\^. There might be some dispute as to whether all these divisions belong to L'chemicalliterature," but each has its utility in the collection of specific kinds of information. Further, the nature of the search may vary; occasionally one merely wants to find the boiling point of a compound at a particular pressure, but on another occasion a complete list of preparative methods might be required. Both the highly detailed encyclopedias and the brief handbooks have their own special usefulness.
order by title, and the languages one may encounter are given by the following code: D = Dutch; E = English; F = French; G = German; I = Italian; L = Latin; P = Polish; R = Russian; S = Swedish. Beginning dates of publication are given in those instances in which it is felt that the information is useful. Class 1. Part 1.
A.
Primary Journals
General and Organic Chemistry
Most Commonly Used lournals
A d a Chemical Scandinavica [E, F , GI Annalen der Chemie (sometimes referred to as Liebigs Annalen) rn7 .
LU,
Classes of the Organic Chemical Literature
1 ) Journals in which original work is puhlished, with experimental details. Discussion of previous relevant work may be expected in a given paper. A summary of the results
of experimental detail (and alsd a minimum of delay). I t is understood that authors of such papers will publish full details later in Class 1. 3) Abstracts, in which papers listed in Classes 1 and 2 me summarieed. These abstracts are usually indexed by author, molecular formula, and subject. In comprehensiveabstracts, patent indexes are included. 4) Lists of titles of journal articles, lists of journal contents, and collections of photostated title pages and tables of contents (all of these are sometimes referred to as "alerting services"). These are essentially reproductions only, with no summaries, and are valuable because they contain information collected from many sources and puhlished very quickly. 5 ) Forward-looking alerting services: Sciace Cilationlndez. 6 ) Beilstein: the encyclopedic reference work of organic chemistry, containing all published data on all compounds reported in certain periods of time. 7 ) Other compilations of organic compounds (shorter than Beilstein, less expensive, less comprehensive in coverage, and eontainine less detail). 8) Review journals, covering certain fields of endeavor, usually of topied interest. 9 ) Bibliographies of bibliographies and reviews, and compilations of indexes. 10) Reference works of synthetic procedures, some of tested and proved worth. Some works devoted to inorganic chemistry will be included in this section. 11) Reference works on methodology, technique, and manipulative methods, including glassblowing. 12) Compilations of data on solubility, dipole moment, kinetics, optical rotations, and absorption spectra, as well as the more common data such as melting point, boiling point, and refractive index. 13) Textbooks, classifying information already available in journsls and abstracts. 14) Patent literature: original patents and patent digests. 15) Reports of symposia, special publications of learned societies, international congresses, etc. 16) Government publications and research reports. 17) Miscellaneous publications, some of limited circulation (e.g., university seminars, commercial product bulletins, manufacturers' literature, and theses). 18) Literature useful though not strictly chemical in nature: literature guides, articles on nomenclature, guides to translation, foreign Language dictionaries, articles on ciphering of chemical structures.
-
In the following lists, most of the more important chemical publications are cited, the basis of choice generally being the frequency with which the publication is quoted as a reference, though it should be recognized that some of the entries represent arbitrary choices on the part of the author. The journals are in alphabetical 194
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lournal of Chemical Education
Bulletin ofthe Academy of Sciaces ofthe USSR (Ituestia AkademiiNauk SSSR) [R] *' Bulletin de la Socidtd Chimipue de France [F] Canadian Journal of Chemistry (before 1951, this was published an the Canadian Journal of Research) [E,F] Chemisehe Berichte (before 1946 the title was Berichte der Dmt schen Chemischen Gesellschajt) [GI Collection of Czechoslovak Chemical Communications [E, G, and oec~sionallyR] Helvetica Chimica A d a [G,F, and rarely El Inorganic Chemistry [El Journal of the American Chemical Society [El Jou~nalof the Chemical Society [El Journal of General Chemistry of the USSR ( Z h u m l Obshchei Khimii) [R] * Journal of Heterocyclic Chemistry [E, F, GI Journal of Inorganic and Nuclear Chemistry [E, F, GI Journal oj Organic Chemistry [El Journal ojorganic Chemistry of the USSR (Zhurnal Organieheskoi Kbimii) IR.1 * Monalshejle fiir Chemie [GI Proceedings of the Academy of Sciences of the USSR (Doklady Akademii Nauk SSSR), Chemistry Section (Otdel. Khim. Nmk) ID1 LA*,
*
Recueil des T ~ a v a v Chimipues z des Pays-Baa [E, F, GI Tebahedron [E,F, GI
0.
Some Less Common Journals
A d a Chimica Academiae Scientamm Hungaricae [E,F, G, R] Arkiv fiir Kemi (changed in 1949 from Arkivf& Kemi, Minerabgi och Geologi) [E,S ] Annales de Chirnie [F] Australian Journal of Chemistry [El Bulletin of the Chemical Society of Japan [El Bulletin des Socidtds Chimiques Belges [D, E, F] Gazzetta Chimica Ilaliana [I1 Indian Chemical Journal [El Israeli Journal of Chemistry [El Journal of Chemistry of the U.A.R. (Vols. 1 and 2 known as the Egypthn Journal of Chemistry) [E, Arabic summary] Journal ofthe Indian Chemical Society [El Roezniki Chemii [E, F , G, PI Zeitschrift fik Naturforschung (Ahteilongen A and B) [G,El Part 11.
Biochemistry and Biarganic Chemistry
Archives of Biochemistry and Biophysics [El Biochemical Journal [El BiochPmist~y[El Bioehimica el Biophysics Acta [E, F, GI Biokhimya [R]a Jollrnal of Biological Chemistry [El Journal of Medicinal Chemistry [El Journal of Molecular Biobgy [El Photochemistry and Photobiology [E, F, GI Phytoehemist~y[E, F, GI An asterisk denotes journak available in English translation from Plenum Press, New York.
Steroids [El Zeitsehrift fiC7 Physwlogisehe Chemie [GI
Part Ill.
Physical Organic Chemistry
Journal of Chemical Physies [El Journal of Physical Chemistry [El Molecular Physics [El Proceedings of the National Academy of Seienees [El P~oceedingsof the Royal Society [El Snectroehimica Acla IE. F . GI
Dissertalion Abstmcts Gas Chromatography Abstraete Iodine Abstracts and Reviews Nuclear Science Abstracts Spectrographic Abstracts. Abstrscts of literature on infrared spectroscopy. Published by Her Majesty's Stationery Office, London, Vol. 1,1955. "The Nucleic Acids." An annotated bibliography of the current literature. Compiled and edited by it. S. SCHAFFENRERG AND R. E. BElm, Special Bibliographies, Loma. Linda, Calif., 1962.
Class 4. Part IV. Analytic01 Methods and Results Analytica Chimica Acta [ E , F , GI Analytical Chemistry [El Journal of Chromatogmphy [E, F , GI Journal of Gas Chromatography [El Talanta [E, F, GI The Analyst [El
Class 2.
Communications
Part I. Journols Devoted to Cammunkafions /3ioch~vtirolo,,diliop1,ysrol llraearcb Cummunvutimts [El Chm icnl Comnrvuvatrom ,[.:I I w ~ g , r n xnnrl .Y,rrlmr Ch~,ni.tryI.rftrrs IE, (;I Tetrahedron Letters [E, F , GI
Part 11.
Journols with a CommunicafimsSection
Acta Chemica Scandinavica [E, F , GI Analytical Chemistry [El Angewandte Chemie [GI (after 1961 available in English ss Ange wandte Chemie, Internationl Edition) Chemistry and Zndustll~[El Chimia [E, F , GI Ezperientia [E, F, G, I] Inorganic Chemistry [El1 Jounal of the American Chemical Society [El Journal of Organometallic Chemistry [E, F , GI Nolure [El Naturwissmchaften [GI Proceeding8 of the Chemical Sociely [El (ceased 1964)' Zeitschrifl jiir Chemie [GI Zeitschrift fur Naturforschung, Abteilungen A and B [G,El
Class 3.
Abstracts or Brief Summaries
Part I. Comprehensive Abrtmct Services For discussion of some of these members, see the second part of this paper. British Chemical Abstrack [El (cessed 1953) Chemical Abstracts [El Chemisehes Zentralblatt [GI Referalivnyi Zhurnal, Khimiya [R]
Part fl. Abrtracts in Rertricted Fields4 Analytical Abstracts "Annotated Bibliographyon the Useof OrganolithiumCompounds in Organic Synthesis," Lithium Corporation of America, Minneapolis, Minn., Vol. 1, 1949. Cancer Chemotherapy Abstracts Carbon-14. A comprehensive annual bibliography of applics, tions in chemistry, biology, and medicine. (Editors: R. S. AND J . K. POLLARD, JR.), Cnlbiochem, Los SCHARFFENRERO, Angeles, Calif., Vol. 1, 1963.
Inorganic Chemistry contains two sections s t the rear of each k u e ; one is entitled "Notes" and the other "Correspondence." The former are essentially short papers, but the latter is a section devoted to the brief discunsion of ideas and results, "NOT Communications to the Editor." a Separate indexes for main articles and communications. ' All journals in thissection are in English.
Alerting Services
Seediscussion in the second part of this paper. Chemical Titles Current Chemical Papers Current Contents Indm Chemicus
Class 5.
Forward-Looking Alerting Services
See discussion in the second part of this paper Science Citalion Indez
Class 6.
Beilstein
See discussiw of Classes 5 and 6 in the third part of this paper.
Class 7.
Other Compilations of Organic Compounds
Chemical encyclopedias and dictionaries consist of collections of information of wide diversity, usually spread over many volumes. In many such works only a relatively minor amount of information may be provided on any item, (e.g., the structure and physical properties of a drug, indexed under a trade name) though articles on technical processes may be much more detailed, especially iu works with a technological emphasis. Two of the best-known works of this type are the following "Encyclopedia of Chemical Technology" (Editorial Board: H. F . M.IRIC,J. J. MCKETTA,JR., A N D D. F. OTHMER), (Snd ed.), volume 1, 1963 (to be published in about 20 volumes, of which 12 volumes had appeared by September, 1967). A first edition appeared in 15 volumes (vol. 1, 1947) with a.fimt supplement in 1957, and a. second in 1960. "Thorpe's Dictionary of Applied Chemistry" (4th ed. in 11 volumes), Longman's, Green, and Co., m d Interscience ( a division of John Wiley & Sons, Inc.), Volume 1, 1937Volume 12 (index), 1956.
Useful dictionaries and encyclopedias on non-industrial subjects are listed below. "Chemistry of Carbon Compounds" (Editor: E. H. RODD) Elsevier, New York, in 5 volumes, some of which are subdivided. Volume 1 (aliphatic), 1951-2 Volume 2 (alicyclic), 1953 Volume 3 (aromatic), 1954, 1956 Volume 4 (heterocyclic), 1957, 1959, and 1960 Volume 5 (miscellaneous and index), 1962 A second edition has been announced, edited by S. Caffey and published by Elsevier in 5 volumes. By 1966, four parts of Vol. 1 had been published, with three more -projected, and other volumes to follow. "Dictionary of Organic Compounds," (Editor: J. R. A. POLLOCK AND R. STEVENS).(4th ed.). Oxford Universitv Press. in 5 volumes, 1965. G p l e m e n t 1, 1965; supplement 2,'1966; supplement 3, 1967. This is a revised version of an earlier fourvolume work edited by I. M. Heilbron and H. M. Bunhury, and published in 1953by Eyre and Spottiswoode, London. "The Encyclopedia. of Organic Chemistry" (Editor-i~ehiej: F. RADT),Elsevier. The following outline gives the original plan, mast of which seems to have been abandoned in favor of Rodd, above, snd Beilstein. Only series 111 has been published. ~
Volume 45, Number 3, Morch 1968
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195
Series I, aliphatic oampounds Series 11, cerboisocyclic non-condensed compounds Series 111. carboisocvclic com~ounds Series IV; heterocych compohds Series 111 runs to a Large number of volumes, and volume 14 (Steroids) has seven recent supplements (1951-1965). Since Beilstein is weak in this area, this series can he very useful. AND z F. "Richter's Organic Chemistry" (Edilors: R. ~ ~ s c a u T REINDEL),3rd English edition, from the 12th German edition of 1935, Elsevier, 4 vols. Volume I, aliphatic series, 1934 Volume 11, alicyclic compounds and natural products, 1939 Volume 111,aromatic compounds, 1946 Volume IV, heterocyclic compounds and free radicals, 1947 "The Ring Index." This is s most useful compilation of data on cyclic compounds. Any system devoid of functional groups (e.g., naphthalene, hut not naphthoic acid) which has been mentioned in the literature will he included. A citation in "The Ring Index" does not guarantee that t synthesis has been achieved, however (for example, I is listed, hut a reference is given to Beilstein, where it is merely mentioned as the parent of several variants). H-N
/\ I
N-H I
Chemical Revinus Forlschritte der Chemie Organischer Natursfoffe [E, F, GI Fortschritte der ChemischenForschuno IE. GI Organic Reactia MechanismP Progress in Infrared Spectrosmpy Inorganic Chemistry Nucleic Acid Research Organic C h i s t y Physical Organic Chemistry Reaction Kinetice Stereochemistry
Survey of Progress in Chemistry Topics in Phosphwus C h a i s h y
Pod 11.
Journals with Regulor or Occasional Reviews'
Anomandte Chemie. Now available in Enelish: see Class 2.
Journal of Chnnical Education Nature Zeitsehrift fzir Chemie [GI
Class 9. H I The rings are clsssiiied by sbe (e.g., I would be classified under 6, for &membered ring), and under each such section there are subdivisions by number of r h g members of each element ( I would appenr under GIN#). By December, 1966, the following volumes were wailable, and 14,265 cyclic systems had been catalogued L. T. CAPELL,AND "The Ring Index," by A. M. PAWEESON, D. F. WALKER,(2nd ed.), American Chemical Society, Wasbington, D. C., 1960. Covers the literature through 1956. "Supplement I," by L. T. CAPELLAND D. F. WALKER,1963. Covers the literature from 1957 through 1959. "Supplement 11," by L. T. CAPELLm n D. F. WALKER,1964. Covers the literature from 1960 through 1961. "Supplement 111," (no authors given), 1965. Covers the literature from 1962 through 1963.
Class 8.
Review PublicoBons5
Pori I. Publicdmns Devoiedto Reviews Acwunts of Chemical Research Advances in Carbohydrate C h i s h y Catalusis ChZiCZ ~ h y s i e s Chemistry Series Chemotherapy Chrwnatography Colloid Science Enzymology Free Radical C h i s t y Heterocvclic Chemishv Inorganic Chentislry and l
