Resonance in organic chemistry

Peter Alexander, Chester Beatty Research Institute, Institute of. Cancer Research, Royal Cancer Hospital, London. Academic. Press, Inc., New York, 195...
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JOURNAL OF CHEMICAL EDUCATION RADIOBIOLOGY SYMPOSIUM 1954 (PROCEEDINGS OF THE SYMPOSIUM L I ~ G E AUGUST-SEPTEMBER, , 1954)

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Z. M.Bacq, Professeur a'l'UniversitQ de Lie'ge, Membre Dorrespondant d e 1'AoadQmie Royale de MQdicine d e Belgique, and Peter Alexander, Chester Beatty Research Institute, Institute of Cancer Research, Royal Cancer Hospital, London. Academic Press, Inc., New York, 1955. d x 362 pp. Many figs. and tables. 16 X 25.5 cm. $9.80.

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Trm volume contains the proceedings of the Radiobiology Symposium held in Liege in September, 1954. The meeting was attended hy scientist,s from 12 countries. There were 15 participants from the United States. The stated purpose of these symposia, which are apparently to be held annually, is to promote exchange of information between physicists, chemists, biologists, and clinicians engaged in work involving the use of ionizing radiation. Most of the 50 papers collected in the present volume are by biologists and they describe studies of the response of intact animals, tissues, microorganisms, and isolated cells to ionizing radiation. A large number of these papers relate studies of protective suhstanoes and methods of influencing r e eove~y. There me three papers on the action of radiation on viruses and enzymes and about six papers on radiation effects in chemical systems. The majority of the papers consist of new experimental work and were written primarily for the specialist. However, anyone engaged in radiation research will probably find this volume of interest in that i t provides a fairly reprcsentat,ive cross section of the ourrent literature in radiobioloev.

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RESONANCE IN ORGANIC CHEMISTRY

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A principal difference between this and the earlier edition is the inclusion of an excellent chapter on the Mathematical Basis of Resonance. This chapter represents no primrose path t o the facile calculation of electron distribution in organic molecules, but the careful reader should obtain an umlemlanding of the methematical basis of both the resonance and the molecular orbital theories. Walling's criterion for the copolymerization of styrene-methyl methacrylate mixtures by cationic and anionic reagents is incorreetlv st,ated on naee 476 but oversiehts of this kind and tvoographical errors are practically abmnt. Tables and i~~ustraiibns are elear and well documented. Although the discussions of molecular orbitals m e of r e d value, the treatment suffers somewhat from an inadequate description of atomic orbitals. Furthermore, the lack of three-dimensional representations (there are only s. handful in the entire book) occasionally causes unnecessary difficulty. Far example, in the discussions of carbon dioxide (page 112), the isocyanides (page 181), and the isocyanstes (page 180), the equivalence or nonequivalence of the structures described would be more readily understood through three-dimensional atomic orbital representations of the molecules. The reviewer would also have welcomed a fuller treatment of the relative stability of organic cations and radicals. However these are minor criticisms. The importance of the resonance viewpoint to organic chemists in general and to graduate students in particular is great indeed. Professor Wheland's able and thoughtful portrayal of the subject deserves their serious attention.

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HAWLEY'S TECHNICAL SPELLER

George Willard Wheland, Professor of Chemistry. University of Chicago. John Wiley & Sons, Ino., New York, 1955. dii 846 pp. Figs. and tables. 16 X 23.5 em. $15.

Gessner G. Hawley, Executive Editor, Reinhold Bock Division, and Alice W. Hawley, Consulting Editor. Reinhold Publishing Carp., New York, 1955. 146 pp. 13.5 X 19.5 cm. $2.95.

TEE 11 years which have elapsed since the appearance of "The Theory of Resonance" (reviewed by A. E. Remick, THIS JO~NA 22,207 L + (1945)) have seen no abatement in the interest and application of resonance to problems of organic chemistry. The new edition, of slightly modified title and over two and onehalf times the length of the original, again takes a careful look a t organic chemistry as approached and interpreted from the resonance viewpoint. The farm and outline is similar to the earlier version, but much new material has been added and old materid has been brought up to date. Of equal importance, the critical care in expression in the first edition has, if anything, been replaced by even greater care in this new edition. The diacussion of the length of the carhon-chlorine bond in ohlorobeneene and that of the centre1 carbon-carbon bond in bibenzyl are two out of many instances in which attention is focused on significant but often overlooked considerations. Chapters I-V and VII-The Theory of Resonance, The Nature of ~ n i c n c r ,1lw0,~:mvc t.:ncrp?., SrrrL. liffcrta of Iksonsnre, lkeonnnvr m d i)il.olr hlomrnts, n ~ r dR w m ~ n c r .and Clwnmir:$l I.:auilil,rit~m-ll:l\.e undrreonr - little e l ~ a-r wfrom the fimt d ~ t i o t i wiih a few important exceptions such as the inclusion of a d e scription of the molecular orbital treatment of valence and recent methods for the calculation of heats of combustion. Substantial additions have been made to the chapters dealing with Resonance and Molecular Speotra and with Resonance and Chemical Reaction. The discussion of the speetrs. of specific classes of organic compounds is of particular value as are the discussions of orientation of substituents in aromatic systems, copolymerization, and molecular rearrangements. The appendix of Interatomic Distances in Orwnic Molecules. which has increased ninefold over the original one, strives for completeness up t o 1954. Among other purposes, i t serves as a highly useful supplement to t,he chapter an steric effects.

OVER8000 words, from a b a m to zymurgy, are alphabetically arranged in very clear, eesily-read columns in this almos6 pockebsized volume. Except for two very short pages on chemical notation, and three pages listing preferred prepositions t o use with such words as correlate . . . (with), the book is devoted entirely to the correct spelling and permissible hyphenation of common technical words.

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W. P. K.

PHYSIOCHEMICAL CALCULATIONS

E. A. G u g e n h e i m , Professor of Chemistry, and J. E. Pme, Lecturer in Chemistrv. .. both of Universitv of Readina.-. Holland. lnrerscience Publishers Inc., New York. 1955. mi T 491 pp. 77 figs. 200 tables. 15.5 X 23.3 cm. $7. ~~

THIB interesting book illustrates the methods of c a v i n g out physical chemist,ry cdculations fromdata. published in theliterature. One hundred and seventy-one problems are worked in different hranches of physical chemistry: Each problem gives data taken from a published article and the reference t o the article. The method of cslculation t o be used is outlined, the use of the data is shown, and the significance of the results is usually discussed briefly. The problems are well aelected, and several errors in printing are corrected by n flyer in the front of the book. Teachers and students should learn a great deal from a study of the hook.

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ARTHUR N O ~ T ~ E A ~ T UNIVBRLITP E ~ N BOBTON. MABBACRDSETTB

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VERNON