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Book Review Chemical Bonding. By M. J. Winter

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Primed for Success
Handbook of Enantioselective Catalysis with Transition Metal Compounds.
Vol. I: Products and Catalysts,
Vol. 11: Ligands-References. By H.
Brunner and W Zettlmeier. VCH
Verlagsgesellschaft, Weinheim/VCH
Publishers, New York, 1993. 917 pp.,
hardcover DM 598.00.-ISBN 3-52729068-0;1-56081-81 1-5
Of the many new specialist books on
chemistry that continue to appear, it is
rare to find one that gives an immediate
impression of being an indispensable addition to the chemical literature. This twovolume handbook on enantioselective
catalysis by Brunner and Zettlmeier is undoubtedly one of these exceptions, in
which the authors have succeeded well in
their aim of bringing some order to the
jungle of chiral metal catalysts and their
reactions. The work excels through being
very up-to-date, through the careful collecting together of the vast amount of
data (covering about 13 000 reactions and
2000 ligands) and the comprehensiveness
thereby achieved. and through the wealth
of inforination that one can extract from
the concisely arranged collection.
The two volumes make up an inseparable whole. Volume I covers reactions with
chiral mctal catalysts, while Volume I1
contains a comprehensive list of all the
chiral ligands known up to about 1992.
Each hgand has been assigned a number,
so that in Volume I each catalyst can be
described concisely by a combination of
the metal with the ligand number.
The reactions in Volume I are arranged
according to the molecular formula of the
product. This is followed by the full reaction equation. in which as much information a s possible has been given within a
This section contains book reviews and a list of
new hook5 received by the editor. Book review are
written h) invitation from the editor. Suggestions
for books to bc reviewed and for book reviewers
Puhliahers should send brochures oI
are ~~elc(iiiir.
(bcttei) books to Di-. Ralf Baumann, Redaktion
Angewandtc Chemie, Postfach 101161, D-69451
Weinheiiii. l-cdcr;il Republic of Germany. The editor resencs the right of selecting which books will
be raiewsd. Uninvited books not chosen for
rcvisu will not bc rcturncd.
small space. The product formulas highlight the chiral centers at which chirality
has been introduced through the action of
the catalyst. This is especially useful in
cases where the educt already contains
one or more chiral centers which are not
configurationally stable under the reaction conditions. Alongside the reaction
arrow are shown the absolute configuration of the product and the maximum optical yield achieved with the first-named
catalyst in the next column. Other catalysts that have been used for the same reaction but gave lower yields are also listed. For each reaction and each ligand all
the relevant literature references are listed
in Volume I1 in order of the year of publication. an unusual and helpful arrangement which allows one to quickly find the
most recent publications.
The only criticism of this excellent
handbook is that one could propose improvements that would allow even more
efficient ways of retrieving the information. Firstly, in Volume I1 the list of ligands does not tell one where to look in
Volume I to find reactions in which particular ligands are used. Secondly, since the
reactions in Volume I are arranged according to the molecular formula of the
product rather than according to reaction
type, it would be useful to have an additional index listing the reactions contained in Volume I according to reaction
types (e.g. hydrogenations, cyclopropanations, etc.) . However, to have included
these improvements would certainly have
increased the size of the handbook beyond that which was intended, and although they would provide extra convenience for the user they would add
nothing to the information content of the
Nevertheless, in view of the continuing
exponential growth in the numbers of
metal catalysts and of their reactions, the
authors should be encouraged to eventually produce a version in the form of a
computerized data bank with all the
searching algorithms that might conceivably be useful.
To sum up. this data collection will be
indispensable for every chemist who is
concerned with chiral molecules. Since it
is reasonably priced I feel justified in rec-
ommending not only that every departmental library should buy the book. but
also that individual research laboratories
should have their own copies.
Oliver Reiser
Institut fur Organische Chemie
der Universitat Gottingen (FRG)
Chemical Bonding. By M . J. Winter.
90 pp., ISBN 0-19-855694-2.-0rganometallics 1. Complexes with
Transition Metal- Carbon a-Bonds.
By M . Bochmunn. 91 pp., ISBN 0-19855751-5.-0rganometallics 2. Complexes with Transition Metal-Carbon
rc-Bonds. By M . Bochmunn. 89pp.,
ISBN 0 - 19- 855813- 9.-Bifunctional
Compounds. By R. S. Wurd. 90 pp..
ISBN 0-19-855808-2.-A11 in the series Oxford Chemistry Primers. Oxford University Press, Oxford, 1994.
Paperbacks, E 4.99 each.
The Oxjbrd Chemistry Primers series, in
which 24 titles have appeared up to now,
aims to provide chemistry students with
simple and quick introductions to specific
areas of organic and inorganic chemistry.
Each volume of about 90 pages contains
material that would be covered in eight to
ten course lectures. The emphasis on explanations and reasoning rather than on
learning facts is intended to equip the student with the basic principles for understanding an area of study.
Chen?icd Bonding is intended for those
just starting their studies. It begins with a
brief historical outline in which the atomic
orbital model and the Periodic System are
developed very lucidly and with little
mathematics. This is followed by chapters
dealing with the bonding between two
atoms. In Chapters 2, after a short section
on the Lewis concepts of the nature of
bonding, the author introduces the principle of a linear combination of atomic
orbitals, with the help ofmolecular orbital
energy level schemes and orbital diagrams. Chapter 3 is concerned with the
VSEPR model, then in the final chapter
the extension of the molecular orbital approach to polyatomic molecules is discussed. The excellent illustrations provid-
ed throughout the volume enable the
reader to gain a good appreciation of the
spatial distribution of the electrons in
atoms and chemical bonds. The representation of orbitals and bonds by electron
density dot diagrams succeeds especially
well. On the other hand it is regrettable
that answers are not provided for the exercise problems included at the end of each
chapter, since this means that they are not
suitable for individual private study by
beginners. Only a few literature references
for more advanced reading are given, but
these are sufficient.
0rgunonic~tullic.s I and Orgunomerullics 2 dcal with compounds containing
metal-carbon o-bonds and rc-bonds respectively. The first of these volumes begins by explaining some basic concepts,
then describes the chemistry of metal carbonyl, metal alkyl, and metal carbene
complexes in turn. 0rgunomrtullit.s 2 begins by briefly repeating and extending
the fundamental principles. then discusses
the most important organometallic rccomplexes. Basic methods of synthesis,
bonding concepts, and chemical reactivities are described for each class of compounds, illustrated by appropriate examples. In each chapter the most
important statements are summarized in
display boxes. Where particular complexes have applications as catalysts for organic syntheses or polymerizations, or as
biosensors. these are highlighted in indented paragraphs. Thus, by clearly emphasizing the essential points, the reader is
given a feel for the relative importance of
the material. In these two volumes also
the illustrations are excellent and contribute to the clarity of presentation. The
ground covered in these volumes is quite
adequate for a first introduction. On the
other hand the indexes (50 and 72 entries
respectively) are rather scanty.
The volume Bifunc,tionul Compounu’s
offers an interesting collection of material
of a kind that is unlikely to be found in
conventional textbooks. It deals with the
chemistry of organic compounds whose
special reactive properties arise from the
presence of two interacting functional
groups. In addition to descriptions of the
synthesis and reactions of dienes, enamines, dicarbonyl compounds, and other
bifunctional compounds. there are chapters on the selective introduction of protecting groups and on cyclizations. The
volume includes exercise problems (with
answers), and is intended for advanced
students and research chemists.
The concept underlying the 0,xford
Cheiiiistrj’ Prinwrs series. whereby the
teaching material is divided into small
subject areas and presented individually,
has the important advantage that the material is more topical and up-to-date than
in conventional textbooks. New developments can be quickly incorporated. and
space can also be given to aspects that are
on the borders of the discipline (e.g. Volume 22 : Frnclu1.s iii Cliemistr~.).
The volumes offer a good basis for small seminars
in which the work could be extended to
suit individual nccds. However. compared
with a comprehensive textbook this teaching concept cannot give such a good
overview of the whole field of organic and
inorganic chemistry. Consequently the
overall perspective and interconnection of
the individual topics must be provided
from some other source. If the volumes of
this series are used as supporting reading
to accompany ;I teaching course. the lecturers will need to link the separate topics
together by providing greater depth and
additional material. If this can be done
effectively, the concept of a textbook of
chemistry made up of units that can be
combined and extended to suit individual
needs could be very successful.
Biirkhard Kiiriig
Institut fiir Organische Chemie
der Technischen Universitiit
Braunschweig (FRG)
Scanning Tunneling Microscopy and
Spectroscopy. Theory, Techniques,
and Applications. Edited by D . A.
Bonnrfl. VCH Verlagsgesellschaft.
Weinheim/VCH Publishers, New
York. 1993. 436 pp., hardcover
DM 196.00, $ 125.00.-1SBN 3-52727920-210-89573-786-X
It can be said straight away that this
book is a must for everyone concerned
with surface physics studies using high
resolution microscopy and microanalysis.
Although it is scarcely a decade since the
invention of the scanning tunneling microscope, it has now been widely adopted
in fields ranging from materials science to
the biological sciences, thanks to the simplicity of the underlying concept and its
remarkable ability to give direct imaging
of atoms and molecules. However, apart
from the short monograph by Hamann
and Heitschold (Akademie Verlag. Berlin,
1992). there has hitherto been no comprehensive treatment of the subject which is
also suitable for newcomers, and gives an
introduction to the principles and main
areas of application. Therefore this book,
by a team of authors who are all actively
engaged in the field, has been compiled
with the needs of advanced students in the
area of surface physics in mind. It will also
be useful to university lecturers in physics,
chemistry, and biology a s a source for
preparing courses. However, it is not intended to be a textbook in the conventional sense; there are many aspects that cannot yet be presented conclusively. as rapid
developments are still taking place. Instead it is more of a snapshot of the
knowledge that experiments have so far
yielded, the theoretical understanding of
which is still at a tentative stage: one such
topic is the role of the conductivity of organic molecules in the generation of scanning tunneling images. According to the
preface the book sets out to bridge the gap
between existing monographs and specialist review articles. for the benefit of the
reader who wishes to make a start in the
field and is interested in the basic principles. the design of instruments. and the
potential applications.
It is to the credit of the editor, Dawn
Bonnell. that the individual contributions
have not been simply strung together in a
haphazard way; instead there is a logical
structure and relationship between the
chapters. which makes the work suitable
a s a course book. It is divided into three
parts. The first part begins with a brief
historical survey of the developments
leading up to the invention of the scanning tunneling microscope. followed by
an exposition of the basic principles: the
construction of the microscope and its
use, the theory of scanning tunneling
microscopy, and the methods of spectroscopy. Part 2 deals with the structure
of the specimen and the probe tip. the two
basic elements involved in image formation. The discussion is mainly concerned
with the surfaces of crystalline solids. their
thermodynamic properties, and the defects of real surfaces. The preparation of
the tip for scanning tunneling microscopy
is then described. along with general aspects of specimen preparation. Part 3.
with the title “Related Techniques and
Applications”. includes an introduction
to scanning atomic force microscopy.
probably the most important of the further developments based on the scanning
probe microscopy principle. This part is
completed by accounts of applications of
scanning tunneling microscopy in electrochemistry and biology.
The book gives a good overview of the
subject, and treats the most important experimental and theoretical aspects with
appropriate thoroughness. However, the
choice of applications strikes me as being
rather arbitrarily restricted. Instead of the
chapter on ballistic electron emission microscopy (BEEM), which should be classified as a ”related technique”, I would
have preferred to see more space devoted
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