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Color Chemistry. Synthesis Properties and Applications of Organic Dyes and Pigments. 3rd revised edition

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Angewandte
Chemie
or NMR laboratory technicians who are
the main target audience for this book,
they can be a valuable working aid or a
means of refreshing ones knowledge.
In NMR—From Spectra to Structures, Terence N. Mitchell and Burkhard
Costisella have set out to provide a practical course in structure determination
by NMR spectroscopy with only the
essential minimum of theoretical “ballast”. The first part consists of 50 pages
describing methods, while the second
part, approaching twice that length, is a
collection of exercises with brief guidance on how to assign and interpret the
spectral features. The style makes for
easy reading almost throughout, with
carefully edited spectra and clear formulas, and thus ones first impression is
very good. However, the guidance on
spectrum interpretation tends to make
it appear that nowadays structures can
usually be determined by NMR
spectroscopy alone, so that using different spectroscopic methods in combination to solve structural problems is
largely unnecessary. On the other
hand, the authors seem unsure about
that view, as they always give an empirical formula and IR band frequencies
with each problem.
The first part of the book begins by
describing 1D NMR spectra and
explaining various important practical
points. That is followed by an introduction to 2D NMR spectroscopy, a chapter
on NMR spectroscopy of quadrupolar
nuclei, and one on coupled HPLC NMR
techniques. Although the authors state
at the beginning that they have avoided
theoretical ballast and concentrated
instead on practical aspects, it is hard
to understand why, for example, they
devote much space to explaining the
Ernst angle thoroughly, but refer the
reader to more advanced books for
explanations of some other simple
basic concepts of practical importance:
the n + 1 multiplicity rule, the Pascal
triangle describing the intensity distribution in multiplets, chemical equivalence,
signal phasing, and spin systems. Concepts such as the T2 relaxation time
and the Karplus relationship are introduced without further explanation, and
the importance of molecular symmetry
in 13C spectra is mentioned but not
explained. Although the repertoire of
1D and 2D NMR experiments that are
Angew. Chem. Int. Ed. 2004, 43, 5290 – 5292
important in modern practice is described, it is not clear why, for example,
under heteronuclear NMR spectroscopy, only 13P measurements are discussed in detail, whereas a disproportionately large amount of space is
devoted to rather “exotic” techniques
such as INADEQUATE, P,C and P,P
correlation methods, 17O NMR spectroscopy, and P,O correlation methods (with
a comment that the latter are not practicable). Some other useful heteronuclear
experiments are not even mentioned.
The authors enthusiasm for their special area of interest becomes evident
when they devote five subsections to
coupled HPLC NMR methods. The bibliography at the end of this first part is
very short (the compilation of tables by
Pretsch is included twice), and is not
up-to-date (in addition to Deromes
book, that by Claridge should also
have been cited).
In the second part, after a brief
survey of other methods of structural
analysis, an example is discussed first
to explain the procedure for determining a structure using the empirical formula, IR band frequencies (wavenumbers), and NMR spectra (1H, 13C,
DEPT or APT, H,H-COSY, and C,H
correlation). That is followed by 35 exercise problems of the same type, with
increasing levels of difficulty. However,
the structures that were solved are not
listed—instead the reader is invited to
contact the authors by e-mail. The
short first chapter discusses the use of
other analytical methods to assist a
structure determination by NMR
spectroscopy. However, elemental analysis and IR spectroscopy are merely
mentioned but not explained, and therefore one must ask how the inexperienced reader is supposed to draw conclusions about the presence of functional groups from the IR wavenumbers
that are given in the examples. Mass
spectrometry is discussed in rather
more detail, although mainly as a vehicle for introducing the determination
of double bond equivalents. The actual
introduction to exercises in the combined use of techniques comes in the
second chapter, and depends more on
an intuitive knowledge of spectra,
rather than describing a general strategy
and leading the novice reader by the
hand. The interpretation of H,H couwww.angewandte.org
pling constants is scarcely discussed at
all, which is perhaps a true reflection
of reality in an age when H,H-COSY
spectroscopy has become routine, but
the authors should at least have discussed the use of coupling constants
data for distinguishing between cis and
trans configurations in olefins.
Despite the books claim to enable
the reader to analyze NMR spectra
without further background information, it only offers a practically orientated collection of exercise problems as
an accompaniment to a course of lectures or a study of more advanced
books. For that purpose it can certainly
be very useful, especially because it
includes a systematic treatment of 2D
spectra.
Nils Schlrer
Institut fr Organische Chemie
Universitt Kln (Germany)
Color Chemistry
Synthesis, Properties and Applications of Organic
Dyes and Pigments. 3rd revised
edition. By Heinrich
Zollinger. WileyVCH, Weinheim
2003. 637 pp.,
hardcover
E 179.00.—ISBN
3-906390-23-3
The authors monograph on color
chemistry has been very familiar to
color chemists for many years. However,
the new edition published in 2003 is not
simply a continuation and updating
from the previous editions, but contains
many new topics, especially those connected with recent applications of dyes
in advanced technologies. Systems
based on light-absorbing chromophores
have an enormous range of potential
applications, and are therefore being
used in an ever-widening variety of tech-
5 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5291
Books
nological fields, so that dyes and pigments are found in situations that are
increasingly remote from their traditional uses for coloring textiles and
paints.
The books introduction begins with
a good survey of important monographs
as milestones in the historical development of color chemistry. The survey
extends up to very recent times and is
topical and up-to-date. This chapter
also provides a good overview of the
industrial production of dyes and pigments. The second chapter discusses
the phenomenon of color, and relates it
to physicochemical processes and to
chemical
structure.
However,
Scheme 2.2 on page 23 is incorrect: for
benzene, with increasing energy in the
region of unoccupied levels it should
show first two degenerate orbitals then
a single orbital. On page 22, the statement that the triplet state is more important for phosphorescence than for fluorescence needs to be corrected (and, in
fact, this point is covered correctly in a
later chapter). Based on the above fundamentals, the author goes on to discuss
the various quantum-chemical calculation methods that are currently used,
and critically compares their merits for
predicting the light-absorption spectra
of dyes. This is especially useful for newcomers to the field of color chemistry, as
they can benefit from the authors wide
experience. Next comes a chapter on
the fluorescence and phosphorescence
of organic compounds, followed by
some empirical rules about color,
which are very useful as guidelines for
the development of new dyes. The pioneering studies by W. K?nig and
W. Ismailsky in 1913 and 1925 are only
touched on briefly (pp. 18 ff). The different methods used in colorimetry are
described, but the fundamental theoretical studies by Richter are not mentioned in this context.
The many types of dyes and pigments are then described, arranged
according to their usual classification.
There are chapters on polyene and polymethine dyes, di- and triarylmethines
and their analogues, aza[18]annulenes,
and nitro and nitroso dyes.
5292
The chapter on azo dyes and azo pigments is appropriately long and
detailed, in accordance with their technological importance and the vast
number of compounds. Much of the
information in this chapter comes first
hand, as the author worked in this area
for many years. However, the statement
that azo dyes are not natural products
needs to be qualified, because 4,4’-azobisphenol (RN 2050–16–0) has been
known since 1984 to be present in
some fungi. The best-known example
of these is the yellow-staining agaricus,
which owes its beautiful red color to
that azo dye; other examples are also
known. The tautomeric equilibria of
azo dyes containing hydroxy or amino
groups are only treated very briefly.
The study of such equilibria has presented a very difficult problem, but a
breakthrough was achieved recently by
NMR spectroscopy, with the surprising
result that practically all the technologically important azo dyes containing
these groups are found to exist in the
form of the hydrazone tautomer.
The azo chapter is followed by
another long one on carbonyl dyes and
pigments. It includes a description of
the classical indanthrene dyes, which
have extreme light-fastness and are
also still much-valued today in the
form of pigments. A separate chapter
is devoted to perylene derivatives; pigments based on these have long been
known for their excellent light-fastness,
but there was little research on the
dyes because of their low solubility.
That situation has changed radically in
the last few years, and the appearance
of over 5000 publications indicates that
these compounds are becoming increasingly important for high-tech applications. Under carbonyl dyes, the more
recently developed DPP pigments are
also discussed; this technologically
important class of organic red pigments
is replacing the inorganic red pigments
that are increasingly proving to be
unsatisfactory. In the following chapter
the author deals with sulfur dyes; these
are technologically important, but in
many cases there is a lack of precise
structural information. This group of
topics ends with a chapter on optical
5 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.angewandte.org
brighteners, which are now very widely
used.
In the remaining third of the book
the emphasis is mainly on technological
aspects of dyes and pigments. In addition to the direct uses of dyes and pigments for coloring, the author discusses
photochemical, thermochemical, and
electrochemical reactions of dyes, and
in this context also describes laser dyes.
Solvatochromic methods for investigating biological structures are described,
but their application to the rapid analysis of binary solvent mixtures is not covered. The rest of the book describes
modern applications of dyes and pigments in data storage, imaging processes, analysis, biochemistry, medicine,
and food coloring, and ends with discussions of environmental aspects and the
toxicology of dyes.
Over the years this book, which
evolved out of the authors original
paperback version, has developed from
an informative book about dyes to
become a standard monograph in the
field of color chemistry. As previously,
I am again impressed by the topicality
and modernity of the book. In this new
edition the author has succeeded very
well in also covering the complicated
subject of functional dyes and integrating this into the work.
It would be difficult to find anything
in the book that could be criticized from
a scientific standpoint. It is valuable
both for getting an overview of the
field of color chemistry and as a mine
of information for the dyestuffs chemist.
Many scientists in other areas such as
biochemistry and medicine are increasingly concerned with the use of lightabsorbing systems in their research,
and I recommend this book unreservedly to everyone interested in the subject. It belongs in every chemistry-orientated library, and also in the personal
bookshelves of every chemist.
Heinz Langhals
Department Chemie
Ludwig-Maximilians-Universitt Mnchen
(Germany)
DOI: 10.1002/anie.200385122
Angew. Chem. Int. Ed. 2004, 43, 5290 – 5292
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edition, chemistry, dyes, color, synthesis, properties, pigment, application, organiz, revised, 3rd
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