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Book Review Molecular Symmetry and Group Theory. By A. Vincent

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techniques by which the problems of assignment can be solved.
Particularly useful is the section entitled “Second Order Effects
in Off-Resonance Spectra”, in which the authors explain why
off-resonance spectra exhibit unusual splitting in certain cases.
The fourth chapter, “Nuclear Spin Relaxation” (23 pages,
33 references), gives a very concise account of 3C spin relaxation, which differs from the otherwise less theoretical approach
used in the book. However, the statement that 13C-NMR
signals relax with a single exponential time constant (p. 129)
is true for methylene and methyl groups only if the cross
correlation is ignored.
Chapter 5 , “Applications”(124 pages, 136 references), constitutes the main part of the book and will soon find its way
into courses on I3C resonance spectroscopy. The principles
given elsewhere in the book can here be put into practice
in numerous aptly chosen exercises, some of which relate
to polymers and biopolymers. The solutions to these exercises
are discussed in detail in an Appendix. This chapter could
be even more useful if it had a better layout. There is only
a subject index, but that contains all the important entries.
An altogether successful, high quality book, essential for
libraries and recommended as a manual to those who deal
routinely with I3C-NMR spectra.
Stefan Berger [NB 400 IE]
Organic Chemistry of Drug Synthesis. By D. Lednicer and
L. A . Mitscher. John Wiley and Sons, New York-London
1977. 1st Edit., xvii, 471 pp., bound, L 16.90.
This book is intended for undergraduates studying medicinal chemistry (where this is offered as a course), pharmaceutical chemists, and organic chemists interested in medical problems. After a short introduction, the authors describe in 21
chapters (432 pages) the synthesis and biological action of
common drugs tested and/or used in the United States. The
book differs from comparable accounts in that, apart from
the chapter on local anesthetics, the chemical structure forms
the basis of the classification and discussion of the pharmacological action. More specifically, we can learn here e.g. about
prostaglandins, steroids, tetracyclines, morphine derivatives,
benzodiazepines, phenothiazines, p-lactam antibiotics, benzyl
and benzhydryl derivatives, phenethyl- and phenylpropylamines, arylacetic and arylpropanoic acids, arylethenes, monocyclic and polycyclic arenes, acyclic compounds, and heterocyclic compounds with five- or six-membered (condensed)
rings. The book ends with a 15-page Cross Index of Drugs
and an 8-page Glossary of the relevant terms. The literature
is covered up to 1971172, and in some cases up to 1974.
Though compact, the work is often stimulating and can
be considered to complement the standard works of Burger
and Ehrhart-Ruschig, to which one should turn for a more
detailed study, even according to the authors of this book.
A particular shortcoming of the latter is that the chemical
formulas are often numbered wrongly.
Bernard Unterhalt [NB 403 IE]
Applications of Biochemical Systems in Organic Chemistry.
Vol. 10. Edited by J . B. Jones, C. J . Sih, and D. Perlman.
John Wiley and Sons, New York-London 1976. Part I:
1st Edit., xii, 505 pages, bound, E 24.25. Part 11: 1st Edit., x,
pages 506-1065, bound, E 26.65.
Part I was written by the editors and three other authors,
and Part I1 by 14 authors; These are either organic chemists
with special interest in enzyme catalysis and particularly its
steric aspects, or biochemists sailing close to chemistry. Since
most organic chemists still largely ignore techniques of biological nature, this work is not without certain missionary zeal.
218
The stress, particularly in Part I, is on the use of enzymes
for asymmetric syntheses, while biotransformations by microorganisms, surveyed in the latest books, are treated only
briefly.
The first chapter in Part I is aimed at familiarizing chemists
with the utilization of biochemical systems. Many readers
will profit from the section on the specificities of enzyme
reactions.
Chapters 2 and 3 (59 and 38 pages, respectively) describe
the use of microorganisms and survey the possible reaction
types.
Chapter 4, with 394 pages the longest in the book, deals
with asymmetric syntheses and enzymatic resolution of racemates. The authors describe in particular proteases oxidoreductases (especially the various alcohol dehydrogenases).
There is extensive tabulated material relating to substrate
specificity and stereospecificity, collected from widely scattered
sources. Much space is devoted to the preparation of compounds that are made chiral by stereospecific isotope substitution. The authors also discuss in detail the application of
biochemical methods to the determination of configurations.
Part I1 is less uniform than Part I. Most of the chapters
are less instructive for practical work, but the book makes
stimulating reading. Rose and Hanson give an excellent 45-page
account of the stereochemistry of enzyme reactions from the
mechanistic and evolutionary points of view, this being an
extended version of an article published in 1975 in Accounts
of Chemical Research.
A . I. Scott gives a 63-page treatment of biogenetic reaction
types, and particularly oligomerization and cyclization with
the incorporation of C--C double bonds, as well as rearrangements.
Guthrie devotes a long chapter (103 pages) to numerous
aspects of catalysis, and deals with enzyme models and related
subjects. In a 60-page account, Cram first discusses the bonds
in complex formation and then mainly his work on host-guest
chemistry, where he mentions many previously unpublished
results as well. Hamilton describes enzymatic redox reactions
and their models in the hope that these enzymes will gain
application as reagents in organic chemistry. The last five
chapters are again devoted mainly to practical aspects, such
as the use of cell-free enzyme systems for organic syntheses
on a large scale, affinity chromatography, immobilized
enzymes, syntheses with reagents on solid carriers, and enzymatic syntheses of compounds labeled with isotopes other
than 2H or 3H.
In all, there are more than 2600 references to research
papers and review articles. Each volume has a subject index
for Parts I and 11. The two Parts are independent, but the
distribution of the material between them is somewhat unclear.
For the specialist this work brings together many facts and
ideas; for the newcomer it can be an excellent catalyst for
using biological systems in preparative organic chemistry.
Helmut Simon [NB 405 IE]
Molecular Symmetry and Group Theory. By A . Vincent. John
Wiley and Sons, London-New York 1977. 1st Edit., ix,
156 pp., bound, E 5.90.
The author first describes the symmetry elements and symmetry groups, and then deals in the next chapters with the
representation of these groups by matrices, determination of
the characters ofa representation, and resolution of a reducible
representation into irreducible ones. He then demonstrates
how group theory can give valuable information about chemical bonds and molecular vibrations. All this is presented
by the method of programmed learning, i.e. in small steps,
each followed by a progress-test question and the correspondAngew. Chem. I n t . Ed. Engl. 1 7 ( 1 9 7 8 ) No. 3
ing answer. If the reader does not give the right answer,
he is told which part of the book he should consult again.
In some cases no mathematical proof is offered, but the author
does state expressly that he finds it more important for the
reader to use the mathematical method correctly than to
be able to prove all the theories.
The book is a really successful attempt at presenting the
scientist with this important and relevant mathematical subject
in the most rational manner possible, in such a way that
the methods can be used correctly for the solution of problems.
It is therefore highly recommended to everyone interested
in molecular structure.
H. G. Zachmann [NB 406 IE]
Iminium Salts in Organic Chemistry. Part 1. Edited by H .
Bohme and H . G. Viehe. Vol. 9 in the series Advances
in Organic Chemistry, Methods and Results. John Wiley
and Sons, New York-London, 1976. 1st Edit., xi, 631 pp.,
bound, $ 32.00.
In the first chapter, entitled “The Electronic Structure of
Iminium Ions” (21 pages), P . A . Kollman gives the results
of quantum-mechanical calculations on the electronic structure, geometry, rotation barriers, and spectroscopic properties
of these ions. In the second chapter, “Structure Determination
of Iminium Salts by Physical Methods” (82 pages), R. M e r h y i
discusses experimental results given in tabulated form and
examines possible equilibria of the type:
H . Bohme and M . Haake’s third chapter, “Methyleniminium
Salts” (1 17 pages), is fundamental from the preparative point
of view. The authors concentrate on the dissociated “N-chloromethylamines”, and their full account of the methods of preparation will impress even the expert, with its brief description
of the physical properties and comprehensive treatment of
the reactions.
In the fourth chapter, “The Vilsmeier-Haack-Arnold Acylations. C-C Bond-Forming Reactions of Chloromethyleniminium Ions” (117 pages), by C . Jutz, the emphasis is placed
on the reactions between dissociated “dichloromethylamines”
(derived from amides) and aliphatic compounds. They go
beyond the Vilsmeier-Haack formylation, since they give not
only aldehydes but also many other products. In Chapter
5, “Chemistry of Dichloromethyleniminium Salts (Phosgeniminium Salts)”(77pages),Z . Janousek and H . G. Viehe discuss
the dissociated “trichloromethylamines”, which are in the same
oxidation state as carbamic acid and whose study did not
start until 1970. The three replaceable chlorine atoms and
the ease of chlorination and aminomethylation open up very
wide synthetic possibilities.
The sixth chapter, “cc-Haloenamines and Keteniminium
Salts” (1 12 pages), by L. Ghosez and J . Marchand-Brynaert,
deals with covalent cc-chloroenamines,which very readily dissociate into ketenimmonium chlorides. Their chemistry is characterized by nucleophilic substitutions of the chlorine atom
(aminoalkylenation), enamine-type reactions, and cycloadditions. Chapter 7, “N-Heteroiminium Salts” (54 pages), by J .
Elguero and C. Marzin, is devoted to immonium salts with
heteroatoms (0,S, N) attached to the nitrogen, examples
being derivatives of hydrazines, hydroxylamine, and sulfenic
acid amides.
This outstanding book is the first to give such a comprehensive and authoritative account of immonium salts. However,
in places one would welcome a more elegant use of formulas
and a word or two about the contents of Part 2.
Giinter Opitz [NB 398 IE]
Angew. Chem. I n t .
Ed. Engl. 1 7 (1978) N o . 3
Fundamentals of Chemical Relaxation. By H . Strehlow and
W Knoche. Vol. 10 of the series “Monographs in Modem
Chemistry”. Edited by H . F. Ebel. Verlag Chemie, Weinheim
1977. x, 133 pp., bound, DM 68.-.-ISBN
3-527-25722-5
Das Arbeiten mit ionenselektiven Elektroden. By K . Cummann.
Vol. 13 of the series “Anleitungen fur die chemische Laboratoriumspraxis”. Edited by F. L. Boschke, V: A . Fussel, W
Fresenius, J . F. K . Huber, E. Pungor, W Simon, and 7:
S. West. Springer-Verlag, Berlin 1977. 2nd, revised and
enlarged edition, xii, 227 pp., bound, DM 76.--.-ISBN
3-540-07947-5
The Use of Chemical Abstracts: A Descriptive Guide to the
Organisation. Development and Use of Chemical Abstracts
and its Associated Indexes. By M . B. M . Campbell. Grifith
University Library, Nathan, Queensland 1977. vi, 37 pp.,
paperback, $ 3.50.-ISBN 0-86857
ESR Spectroscopy in Polymer Research. By R . Riinby and
J . F. Rabek. Vol. 1 of the series “Polymers-Properties
and Applications”. Edited by H.-J. Cantow, H . J . Harwood,
J . P . Kennedy, J . Meissner, S , Okumura, G . Olivi, and S.
Olive. Springer-Verlag, Berlin 1977. xiv, 410 pp., bound,
DM 112.--.-ISBN
3-540-08151-8
Grundlagender TechnischenElektrochemie. Erweiterte Fassung
eines Dechema-Experimentalkurses. By E. Heitz and G.
Kreysa. From the “reprotext” series. Verlag Chemie, Weinheim 1977. xiv, 290 pp., paperback, DM 48.-.--ISBN
3527-25754-3
Gmelin Handbuch der Anorganischen Chemie. Springer-Verlag,
Berlin 1977, 8th edition.
Erganzungswerk, Band 45 : Borverbindungen. Teil 14: BorWasserstoff-Verbindungen I.xxii, 310 pp., bound, DM
704.-.-ISBN
3-540-93341-7
Hauptwerk, System-Nr. 14: Kohlenstoff. Tell D : Die Verbindungen. Lieferung 5 : Kohlenstoff-Schwefel-Verbindungen
(Fortsetzung). xxvi, 237 pp., bound, DM 571.-.-ISBN
3-540-93342-5
Hauptwerk, System-Nr. 46: Zinn. Tell C: Die Verbindungen.
Lieferung 5 : Komplexverbindungen des Zinns. xxiv, 246
pp., bound, DM 613.-.-ISBN
3-540-93345-X
Hauptwerk, System-Nr. 55 : Uran. Erganzungsband, Teil
C: Die Verbindungen. Lieferung 1: Verbindungen mit Edelgasen und Wasserstoff sowie System Uran-Sauerstoff. xx,
206 pp., bound, DM 521 .-.-ISBN
3-540-93344-1
Gmelin Handbuch der anorganischenChemie. Erganzungswerk,
Band 46: Borverbindungen, Teill5: Amin-Borane. SpringerVerlag, Berlin 1977. 8th Edit., 170 pp., DM 407.-.-ISBN
3.540-93347-6
Quantum Pharmacology. By W G. Richards. Butterworths,
London 1977. xiii, 213 pp., bound, E 12.OO-ISBN 0-408709 19-7
219
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