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Book Review The Molecular Orbital Theory of Organic Chemistry. By M. J. S. Dewar

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The numerous illustrations and tables enhance the value of
this book, which combines experiment, theory, and individual results (including crystal structure and crystal chemistry).
The reviewer has read it with considerable interest, and has
formed the opinion that it will be found very useful by student
R. Hoppe [NB 845 IE]
and teacher alike.
The Molecular Qrbital Theory of Organic Chemistry, By M.
J. S . Dewur. From the “McGraw-Hill Series in Advanced
1969.
Chemistry”. McGraw-Hill Book Corp., _NeE-,,Y&
1st Edit., xiv + 484 pp.. numerous figures and tables,
bound, approx. D M 74.-.
The book is highly ambitious right from the word go. It represents a n attempt to derive organic chemistry from the
principles of quantum mechanics. By bringing in such heavy
artillery as Dirac’s Bra-Ket formalism in the very first chapter
th’e author risks frightening away readers who would be
quite capable of following the rest of the book. Quantumchemical approximation methods are discussed in Chapter 2,
semi-empirical methods of quantum chemistry in Chapter 3,
and a n outline of the theory of atoms and small molecules is
presented in Chapter 4. Two-thirds of the book deals with
the properties of organic molecules, e.g. their bond energies
and their stability, as well as the problem of aromatic character (Chapter 5), and the mechanisms of chemical reactions
(Chapter 8). The theory of U V spectra is deliberately omitted,
but o n the other hand we find something on the MO theory
of electron spin resonance (Chapter 7). A separate chapter
(9) is reserved for aromatic systems with heteroatoms, and
finally, in Chapter 10, we are told something of the topical
field of the quantum chemistry of a-bonds.
As regards methods, the central position in the book is occupied by Dewar’s version (i.e. the one parametrized for
properties of the ground states) of the semi-empirical PariserParr-Pople method for x-electrons, abbreviated by the author
to “Pople method”, for the usefulness of which he adduces
convincing comparisons from experiment and theory. However, the justification for the Pople method (in particular for
the neglect of differential overlapping) is not entirely convincing. The Hiickel MO (HMO) method is very elegantly derived
from that of Pople, the derivation clearly revealing both the
limitations and the possibilities of the H M O method (provided, of course, that one has previously allowed oneself to
be persuaded of the admissibility of Pople’s approximations).
4 s a n alternative to the Pople method the author offers a
perturbation-theory simplification o f the H M O method
(called PMO), which makes use in particular of the properties of alternant hydrocarbons. This method is very neat and
no doubt quite useful since it yields important results with-
out computation, but it is not so straightforward as one might
think after reading Chapter 6.
The book disposes of a number of traditional misconceptions, although the discussions sometimes tend to get out of
hand.
One will not begrudge the author his tendency to highlight
his own work, in many cases to excess, but he would have
done better to resist the temptation to include the “SPO
method”, which can claim no more than historical interest
either in its first or in its second formulation.
Despite any reservations that one may have o n points of
detail, one must in fairness admit that there exists n o other
textbook of theoretical organic chemistry on a comparable
Werner Kutzelnigg [NB 859 IE]
level.
The Chemistry of the Nitro and Nitroso Groups. Part 1.
Edited by H . Feuer. From the series “The Chemistry of
Functional Groups”. John Wiley and Sons Ltd., k . n d m
New York 1969. 1st Edit., xii + 771 pp., numerous formulas and tables, 281 s.
This book, the first of two volumes to be devoted to the nitro
and nitroso groups, forms part of the series “The Chemistry
of Functional Groups” edited by S. Putui. It contains nine
chapters, written by a total of ten authors, on theoretical
aspects of C-NO and C-NOz bonding, the spectroscopy
and photochemistry of the two groups, the formation and the
reactions of the nitroso group, the formation of aliphatic and
alicyclic nitro compounds, of nitronic acids and esters, and
of nitroamino groups. There is also a chapter on the activation of nucleophilic aromatic substitution by nitro groups.
The introduction includes a summary of the chapters and
authors of the still awaited second volume. Among other
things, it indicates that the formation of aromatic nitro compounds, the effect of nitro groups o n electrophilic and radical
aromatic substitutions, and the Meisenheimer complexes of
nitro compounds will be discussed only in this future volume.
It can be seen that the final topic of the first volume fits more
properly within the overall framework of the second. From
remarks in the preface i t may be gathered that this faulty arrangement of chapters is due to the late arrival of some of the
manuscripts. In our opinion the publisher should have found
a way of avoiding this fundamental weakness of multi-author
publications. Since a critical discussion of the first (fragmentary) volume without a knowledge of the contents of the
second volume would not be altogether fair to the authors
whose contributions have already appeared, the review of the
entire work will be held over until the publication of the
Heinrich Zollinger [NB 858 IE]
second volume.
Registered names, trademarks, etc. used in this journal, even withour specific indication thereof, are not to be considered unprotected by law.
Q Verlag Chemie, GmbH, Weinheim 1970.
- Printed in Germany by Druckerei
Winter, Heidelberg.
All rights reserved. N o part of this journal may be reproduced in any form whatsoever, e.g. by photoprint, microfilm, or any other means, without
written permission from the publishers.
Editorial office: Ziegelhauser Landstrasse 35, 6900 Heidelberg 1 , Germany, Telephone 45075, Telex 46 18 55 kemia d, Cable address: Chemieredaktion
Heidelberg.
Editor: H . Grunewald
‘
Translation Editors: A. J . Rackstraw and A . Stimson.
Publisheis: Verlag Chemie, GmbH. (Presidents Jijrgen Kieuzhage and Hans S c h e m e r ) , Pappelallee 3 , 6940 Weinheim/Bergstr., Germany, and
Academic Press Inc. (President Wolrer J. Johnson), 111 Fifth Avenue, New York 3, N.Y., USA, and Berkeley Square House, Berkeley Square,
London, W. l . , England.
Correspondence concerning advertisements should be addressed to Verlag Chemie, GmbH. (Advertising Manager W.Thiel), 6940 Weinheim/Bergstr.,
Pappelallee 3, Germany, Telephone Weinheim (06201) 3635, Telex 4655 16 vchwh.
180
Angew. Chem. infernat. Edit.
1 Vol. 9 (19701 I No. 2
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