An algorithm for translating chemical names to molecular formulas

An algorithm for translating chemical names to molecular formulas (Garfield, Eugene). F. A. Landee. J. Chem. .... When Good Bees Go Bad. Honeybee ...
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SAULL. GEFFNER Toleest Hills High Schol Forest Hills. N w York

An Algorithm for Translating Chemical Names to Molecular Formulas

Eugae Gal.field, Institute for Scientific Information, Philsdelphia. Institute for Scientific Information, Philadelphia, 1961. ix 68 pp. Tables. 21.5 X 28 cm. SF.

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This monograph, which is derived from s doctoral dissertation in linguistics, explains an algorithm which may be used to calculate the molecular formula to an organic compound from its chemioel name. The use of this algorithm, upon numerous examples both manually and with an electronic digital computer, illustrates the ~rinciplesand techniques involved.

The paper begins with s discussion of the nature and usage of systematic chemical nomenclature and of the problems of representing chemical structures. The author speaks with knowledge on these matters from his experience as editor of the "Index Chemicus." The linguistir approach to the prohlem is then explained. I n this case this means the study of a large body of chemical names and isolating by this method the basic units of the English language that are used in chemical nomenclature. These units, termed morphemes, are rather less than words and are rather more syllabic in character. The meanings, and relationships, and implications toward molecular formulas, of these morphemes are then studied and an inventory list of 60 such terms presented. Examples are: "aYaa used in ethanal. Implies the presence of one oxygen atom and one double band. "Yne"-ss used in butyne. Implies no atoms, but, doos imply the equivalent of two double bonds. These implications are termed the dictionary or eslculation values of the morpheme. Even within this s m d l lint (which was derived from relatively restricted classes of organic campounde) different classes of morphemes appear, such as bonding, multiplicative, and synomic ( a h ) morphemes. In addition various ambiguities exist and must he recognized and properly treated within the framework of the algorithm. The pentmct ambiguity (ituthor's terms) is a case in point. The

ambiguity here may be illustrated by the name: penta chloro pmtane I t is obvious that here the two uses of the morpheme "pent," have different meanings and are derived from different sources. The algorithm itself is a set of eight rules for systematically recognizing the morphemes in 8 name and substituting for the morphemes their dictionary values in a. multiplying and summing formula. This formula gives the atoms of carbon, of nitrogen, of oxygen and of sulfur, in the molecular formula when the indicated arithmetic is carried out. The hydrogen atoms are then calculated by a separate formale using the indicated atoms and the double bond values from the morphemes. The derivation, in part, of these formulas from previous published work of Soffer (Scimce. 127: 880, 1958) is acknowledged. The paper is very interesting from several standpoints. I t does illustrate the advantages of an interdisciplinary approach to what many might consider strictly a chemical problem, and it does open the door s little wider for the entrance of the computer into these problem itreas. There is no doubt that thousrtnds of compounds of considerable complexity can be G U C C ~ S S ~processed UII~ by the procedures so far devised. The reviewer doubts that m y sizeble fraction of the (Continued on page A558)

Volume 39, Number 7, July 1962

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BOOK REVIEWS known compounds today could be so handled. The eritioal question is this-as the system is extended (as i t certainly should be), which increases the faster, the classes and fractions of known compounds which can be handled, or the "ambiguities," the "exceptions," the "special procedures" and "devices" which must he added to the algorithm? F. A. LANDEE The D m Chemical Cmnpany Midland, Michigan

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Searching the Chemical Litamlure

Edited by Robert F. GmM, American Chemical Society Applied Publications Advances in Chemistry Series, No. 30. ACS, Washington, D. C., 1961. vi 326 pp. Fim. and tables. 16 X 23.5 cm. $6.50.

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The American Chemical Society published the first edition of this book in 1951 as Advances in Chemistry Series No. 4. It contained about 20 articles selected from the 1947 and 1950 symposia. of the Divisions of Chemical Education and Chemical Literature. Four printings failed to satisfy the demand for the guide so T. E. R. Singer scheduled a 1956 symposium to promote the revision now available. This new edition contains almost all of the articles in the earlier volume with additions and changes t o make a wellbalanced, up-to-date group of 31 papers covering sources and techniques of chemical lihrary research. The chapters vary in length from three to 27 pages and contain bibliographies totaling over 800 citations, all brought doto 1960-61. The subjects included are searching techniques, patents, indexes, nomenclature, abstracts, German and Russian literature, reporta and their preparation, older and less familiar periodicals, medicinal chemistry, abbreviations, theses and doctoral diseertationa, house organs, trademarks, government documents, and mechanioal searching. The last four articles are devoted to outstanding libraries-The Chemists' Club, New York Public, KresgeHooker, and John Crerar-their holdings and services. Uniformly high quality and reliability of these papers are assured by the standing of the approximately 40 specialists who m o t e them, from E. J. Crane, requiring no introduction, to Julim F. Smith, the veteran bibliographer a t e m in many languages. Thi. timely survey of techniques, toole, and sources deserves a place in every library fostering chemical research. In addition many of the articles can he used for assignment in chemical literature courses and schools of library science. Everyone interested in promoting the advance of chemistry will find this revision full of helpful material. BYRON A. SOULE University of Michigan Ann Arbor

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Journol of Chemical Education