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Book Review Organic Chemistry in Colour. By P. F. Gordon and P. Gregory

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BOOK REVIEWS
The Chemistry of the Metal-Carbon Bond. Vol. 1: The
Structure, Preparation, Thermochemistry and Characterization of Organometallic Compounds. Edited by F. R .
Hartley and S . Patai. John Wiley, Chichester 1982. xii,
1071 pp., bound, .f 125.00.
According to the editors’ foreword this book is the first
volume of a series covering the highly topical field of the
chemistry of organometallic compounds and should (again
according to the foreword) be of particular interest to organic chemists. Whether it achieves this aim is, however,
questionable. The subtitle itself is confusing; even though
without index there are 969 pages available nothing is said
about the preparation and almost nothing is said about the
structure of the organometallic compounds of the main
group elements; in other words not a word about Grignard
reagents, nothing about organolithium compounds (apart
from the structure of CH3Li and the enthalpies of formation of C2H5Li and n-C,H,Li), nothing about organoaluminum, organozinc, organocadmium, organomercury compounds (apart from some thermodynamic data) and all
that for the princely sum of .f 125 (!!). It is stated in the
foreword that the editors had other ideas concerning the
arrangement of this and the succeeding volumes, but that
is not consolation to the reader. What a pity-particularly
when one considers the contents of some of the chapters
(there is a total of 22).
Chapter 1 of the book (A. D . Redhouse) deals in very
concentrated form with the structures of organometallic
compounds (more precisely organotransition metal compounds) but unfortunately omits any reference to their
bonding relationships. Anyone wishing to know why a
compound like C,(CH3),RuC8H8 possesses the structure
given on p. 26 has to wait for the following volumes and
hope to find an answer there. Have the editors not heard
of “Structure and Bonding”? Chapter 2 (G. Pilcher and H .
A . Skinner) covering thermodynamic aspects is significantly more informative. Here one learns where details
concerning enthalpies of formation and bonding energies
are to be found and where the difficulties lie in such investigations. The next 4 chapters-Synthesis of ylide-metal
complexes (L. Weber), Carbenemetal complexes ( H . Fischer), Carbyne-metal complexes ( U . Schubert) and Alkyl and
aryl transition metal complexes ( R . J. Puddephatt) are similarly competently produced. Here it can be seen that the
authors are themselves active in their respective fields and
understand their metiers. This also applies to Chapter 12
(Synthesis of organolanthanide and organoactinide complexes by W. J . Evans) and 13 (Metal atoms in organometallic synthesis by M . J. McGlinchey), in which, pleasingly-as the interested reader would expect-also the most
recent literature (1980 and 1981) is taken into account.
This ought to be automatic-at least in a book that the editors wish to present as a standard work.
Chapters 7 and 9- 11 on the synthesis of q3-allyl complexes (P. Powell) and complexes with q4,q’, $, q7 and q8
coordinated ligands (G. Marr and B. W. Rockett) are somewhat less up-to-date than those mentioned above and only
provide a limited view of the “state of the art”; they lack
references later than 1979 and the sovereignty of choice,
which is featured in Chapters 12 and 13 for example.
Chapters 14-19 (by T. R. Crompton 180 pp.) are largely
superfluous. Anyone wishing to know how to determine
Pb(C2H5), in gasoline, how to ascertain the carboxyhemoglobin content of blood and how to measure small quantiAngew. Chem. Inl. Ed. Engl. 24 (1985) No. I
ties of H,Se in air (where is the metal carbon bond?) will
probably inform himself from the standard analytical literature. One seeks in vain, here, for any connection with the
reality of the practical preparative organometallic chemist,
who characterizes his compounds by elementary analysis
(which he does not usually perform himself) and by spectroscopy.
These spectroscopic methods are discussed in Chapters
20 (IR and Raman by M . J . Taylor), 21 (NMR by J . A.
Davies) and 22 (MS by T. R . Spalding). The treatment of
the application of N M R spectroscopy deserves unstinting
praise; it its exceedingly informative and takes account of
both theoretical and practical problems. There is no doubt
that an engaged author was at work here, who did not shy
at the effort of including the latest publications (from 198 1
and 1982) in an appendix. This is missing in the chapter
concerned with mass spectroscopy, in which the treatment
of such currently important areas as field ionization and
field desorption techniques is crammed into half a page.
Finally the question-who is going to buy it‘? And above
all-who can pay for it? Are the editors of such series and
the publishers not aware of the situation in the universities
today (not only in the Federal Republic of Germany)? In
view of just this situation, should one not consider more
critically and scrupulously how best to serve the readerand here this means the organometallic (and organic)
chemist-at his place of work? The present work does not
exhibit signs of such considerations and that has to be laid,
above all, at the door of the editors. It is scarcely possible
to recommend purchase under present conditions.
Helmut Werner [NB 644 IE]
Institut fur Anorganische Chemie
der Universitat Wurzburg
Organic Chemistry in Colour. By P. F. Gordon and P. Gregory. Springer-Verlag, Berlin 1983, xi, 322 pp., bound,
D M 178.00.
Dyestuffs chemistry is applied organic chemistry. Since
it is mainly practised in the laboratories and finishing
shops of the dyestuff manufacturers, this review, written
by employees of one of these companies (ICI), deserves
particular attention.
The book, which is almost exclusively devoted to textile
dyes, begins in Chapter I with a retrospect, which covers
the period before Perkin through the structural assignment
of the natural dyestuffs u p to the most recent areas of
dyestuff application.
Two sections of Chapter 2 with cleverly chosen and generalizable examples of the synthesis of dyestuffs and intermediates will meet with approval. Probably these sections
would have been enriched if Chapters 3 to 5 had followed
this pattern and emphasized market and environmentally
oriented synthesis strategies more markedly. The normal
classification method, whereby textile dyes are divided
into a maximum of seven main structural classes, has been
effectively adopted. A second classification principle and
its influence on the C.I. (Color Index) dyestuff names,
which are frequently quoted in this work, ought to have
been explained in more detail in view of the heterogeneous
readership. However, to devote a section to classification
principles is not very helpful if the care has not been taken
which is necessary for the coordination of individual struc75
tural features or even if both principles are combined. The
headings to 2.2.3 and 2.4.3 (vat dyestuffs) and most of subsection 2.2.9 (miscellaneous) in particular can be criticized
on these grounds.
Phenylogue polymethine dyestuffs, alongside the cyanines the most important class with delocalized charge, are
grouped under the heading arylcarbenium. Inconsistently,
however, it is left to the reader to place the charge sign in
the correct place in the formulas or to search (in vain) for a
carbenium center. May be because of the (apparent) dilemma with mono and pentamethinecyanines, the authors
exclusively employ inapplicable resonance formulas with
the charge o n one of the heteroatoms, which cannot be
said to be acceptable nowadays for anything other than to
illustrate a symmetry-hostile nomenclature (Chemical Abstracts, cyanines).
The main concern of the authors is obviously the interaction between structure, chemical and physical properties, on the one hand, and marked value, on the other,
which may to some extent justify the size of Chapters 3-5.
Chapter 3, azo dyes, is introduced by a short section concerning the structure of the basic chromogen. The section
on tautomerism emphasizes the relationship between substitution, equilibrium position and extinction. A further
section is concerned with metal complexes including some
aspects of complex isomerism. The section on constitution
and color gives the same weight to a review as to the results of MO treatment. Chapter 4, anthraquinone dyes, is
similarly constructed, while the remaining structural
classes are treated somewhat more briefly in Chapter 5 .
The discussion of textile fibers is reduced to a minimum
and included in Chapter 6. The section on application and
wet fastness is very clearly laid out with a classification according to bonding principles; there is no mention of a
competing concept which views the binding of direct dyestuffs to cellulose in terms of the demonstrable-to be sure
only in solution and on films-aggregate formation. Light
fastness is also discussed in detail; key words are test
methods, photochemical principles, attempts to clarify the
bleaching mechanisms, catalytic processes, photochemical
fiber damage. Short sections concerning fastness to sublimation, solvolysis in the dyeing vat, fastness to bleaching,
solvatochromism, photochromism and metamerism round
off the chapter. Extensive reference lists are included at
the end of each chapter and (concerning M O theory, colorimetrics and the often neglected facet of color perception)
in the appendix.
This book is primarily intended for readers practising
the subject. Students of chemistry and possibly of textiles
will find a wealth of useful information, which will not replace lectures on dyestuffs but can usefully complement
them. A book that deliberately sets its accent differently
and (the criticisms mentioned above excepted) a book that
can be recommended.
Dieter Schelz [NB 643 IE]
Institut fur Farbenchemie
der Universitat Basel
Reihe Hochschultexte. Chemische Aspekte der FestkorperPhysik. By H. Endres. Springer-Verlag, Heidelberg 1984.
iv. 160 pp., stitched, DM 42.00.--ISBN 3-540-13604-5
Methods of Enzymatic Analysis. By H. U. Bergmeyer. Vol.
V: Peptidases, Proteinases and Their Inhibitors. Verlag
Chemie, Weinheim 1984. xxvii, 558 pp., bound, subscription price: D M 235.00; later, price per volume: D M
270.00.- ISBN 3-527-26045-5
Biotransformation von Arzneimitteln. Vol. 5. By S. Pfeifer
and H.-H. Borchert. Verlag Chemie, Weinheim 1984.468
pp., bound, DM 168.00.--ISBN 3-527-26075-7
Corrigendum
The following correction should be made to the communication entitled “Synthesis and Structure of the 7-Trifluoromethyl-1,3,5,2,4,6,8-trithiatetrazocine Cation” by H.-U.
HO$, G. Hartmann, R . Mews, and G . M . Sheldrick, Angew. Chem. Int. Ed. Engl. 23 (1984) 988:
In Formula 1 the chlorine substituents should be attached
to the sulfur atoms and not to the nitrogen atoms.
Rpqi(.iewd names. rrademorks, p i c used in rhrs journal, euen wirhour spec& rndirarron rhereo/, are 1101 10 he considered unprorerrrd hv laa
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76
Anyew. Chem in!. Ed. Enyl. 24 fl985) No I
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