stlrutlun to be on the clcctrunir prr~pvrties of thr n~olrrule3nd to be simthr to nornml substnucnt eNectr. The vaiionv oi this concept is then examined in detail in terms of formal theorv and exmrimental kinetic
BOOK
REVIEWS
Progress in Physical Organic Chemistry. Volume 1 Edited by Saul C. C o h a , Brandeis University, Waltham, Massachusetts, Andrew Streitzuieser, JY., University of California, Berkeley, and Robert W. Taft, Pennsylvania State University, University Park. Interscience Publishers ( a division of John Wiley .and 411 pp. Sons), Kew York, 1963. ix Figs. and tables. 16 X 23.5 cm. $15.
+
The first volume of the present series consists of five articles. The authors, as is proper, have all been active in the fields they are reviewing. The editors are to be congratulated for their choice of topics. In addition to selecting subjects eunently being investigated, the editors and authors have managed to indicate several areas seriously in need of further study. Future editions will be more u s e ful and reliable if the time lapse between the preparation and publication of the ruticles can be reduced. Judging from the bibliographies in the present volume, this time lapse was at least twelve montha. The most remarkable feature of the book is the variation in scope of the articles. They range from concise summaries to comprehensive reference work. Ionieation Potentials in Organic Chemistry are reviewed in a very succinct, critical and lucid manner by A. Streitwieser, Jr.
-Reviewed
The accomplishments of the field are neatly summarized and the disturbing lack of agreement between experimental methods is clearly indicated. S. D. Ross's chapter on Nucleophilic Aromatic Substitution Reactions deals almost exelusively with the role of an intermediate in the hiomolecular mecbaniem for such reactions. The scope ie thus rather narrow and the arguments and data consequently relatively detailed. Ross's treatment of isotope effects is, at best, misleading. In general, this chapter and the following one by Lichtinlack the aspect of clean, cogent. summary found in Striee wieser's chapter. lonizatition and Dissociation Equilibria in Solution in Liauid Sulfur Dioxide bv N. N. Lichtinp resents a timely and cogstructive review of recent work. The results of conductance investigations of dissociation and ionization equilibria are clearly and critically presented. The reviewer found the results and conclusions instructive with regard to ion behavior in heterolytic reactions. In contrast to the previous chapters, the last two, comprising 75% of the book, should be useful as reference works rather t h m as reviews or summaries. E. A. Halevi's chapter, Secondary Isotope Effects, makes a serious attempt to weave the numerous and seemingly diverse observations concerning secondarydeuterium isotope effects into a coherent fabric. Halevi considers the effect of isoto~icsub-
in this Issue
Saul G. Cohm, Andrezu Sf~eitwieser,Jr., and Robert W. Taft, editors, Progress in Phyaical Organic Chemistry. Volume 1 Wilhelm Foersf, editor, Newer Methods of Preparative Organic Chemistry. Volume 2 Cmwin Hansch and George H e l m h p , An Outline of Organic Chemistry Louis F. Fieaet and Mary Fieaer, Topics in Organic Chemistry Peter Karlsn, Introduction to Modern Biochemistry J . Leggett Bailey, Techniques in Protein Chemietry Roy L. Whistler, M. L. Wolfram, and James N. BeMiUer, editors, Methods in Carbohydrate Chemistry. Volume 2, Reactions of Cmbohydrates Roy L. Whistler and M . L. Wolfrmn, editors, Methods in Carbohydrate Chemistry. Volume 3, Cellulose Dale H . Busch, symposium chairman, Reactions of Coordinated Ligands and Homogeneous Catalmia Herschel Smizh, Chemistry in Nonaqueous Ionizing Solvents. Volume 1, Part 2, Organic Reactions in Liquid Ammonia T m U L. Hill, Thermodynamics of Small Systems. Part 1 Robert K . Willardson and Harry L. Goering, editors, Compound Semiconductors. Volume 1, Preparation of 111-V Compounds C. A. McDowell, editor, Mass Spectrometry Anders Ringborn, Complexation in Analytical Chemistry F. Gordn Smith, Physical Geochemistry Robert H. P m y , Cecil H . Chilton, and Sidney D. Kirlcpat~iek,editors, Chemical Engineer's Handbook
350
/
Journol of Chemical Education
comprehensive reference work. The theoretical foundations of the methods, the experimental methods and the rosults are presented clearly and in detail. The chapter contains extensive tables of basicity data. In spite of the scope and thoroughness of the coverage, the data have been carefully and critically selected.
J. A. &MPMEIER University of Rochester Rochestar, New York
Newer Methods of Preparative Organic Chemistry. Volume 2 Edited by Wilhelrn Foe& Translated by F. K. Kirehne?, Sterling-Winthrop Research Institute, Rensselaer, New York. Academic Press, Inc., New 417 pp. Figs. and York, 1963. xv tables. 10 X 23.5 cm. $14.50.
+
Thk book is a translation of a collection of fourteen review articles originally published in Anoewandte Chemie. Like the
actions, although it contains a generous sprinkling of modern structural and mechanistic concepts. For example, the c h a p ter by R. Criegse on oxidations by lead tetra-acetate might be considered a revision of a similar chapter in Volume I, where several uf the oxidation reactions are now correlated by an ionic mechanism involving the intermediates R P ~ ( O A C ) ~ or ROPb(0Ac)s. Several chapters deal with individual reactions, such as the reduction of carbonyl compounds by complex hydrides, which stresses selective reductions and orotection of functional erouns. Other
we find reviews on syntheses with acetoacetaldehyde, ketene, and ethyl 2-cyclopentanecarboxylate. The unique ortho orientation by aluminum salt catalysts in the nuclear alkyls, tion of aromatic amines and phenols is discussed in two well-written chapters by R. Strob and cc+workers. Amidomethylation as an important adjunct to the Mannich reaction is discussed by H. Hellmann. A review of the chemistry of organic phosphines by L. Homer and H. Hoffman includes evidence far the structure of many adducts. Another interesting chapter is that on selective catalytic oxidation by molecular oxygen over noble metal catalysts. Far those whose interests tend towsrd natural products and biochemical topics, the chemical syntheses of seven intermediate phosphrate esters in the Enlbden-
