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Prentice Hall: Upper Saddle
River, NJ, 1998. viii + 568 pp. ISBN 0 13 258690 8. $76.00.
This book will be a welcome addition to the library of
any organic chemist and will be particularly useful as a text
for graduate and advanced undergraduate courses
emphasizing spectroscopy as a structure determination tool. Its
coverage and level are ideal, between the introductory organic
and physical chemistry courses and real structural problems
which require a deeper and broader understanding of methods
and interpretation to solve. It also bridges a gap in texts,
between the introductory organic texts, specialized monographs
on individual methods, and instrumental analysis texts.
One advantage of this book is that it reflects current
research practice, as it was written by experts in each
spectroscopic technique. Some traditional topics, such as
scanning NMR spectrometers, are barely mentioned. Replacing
them are NMR relaxation times, the nuclear Overhauser
effect, DEPT, COSY, HETCOR, NOESY, TOCSY, etc., and
MS ionization techniques such as CI, DI (SIMS, FAB,
PD, MALDI), and electrospray. Such a collaboration has the
potential for inconsistency in level and approach;
however, the four authors have clearly worked as a team to produce
a well-organized and consistent text.
There are four core sections, on nuclear magnetic
resonance (NMR), vibrational (IR), electronic, and mass
(MS) spectra. Each section has about three chapters. The
first, "Introduction and Experimental Methods", provides
integrated theory for the whole section. For example, the first
chapter in the electronic section describes the relationships
between UV-vis absorption, CD, and ORD; the first
chapter in the vibration section relates absorption and Raman. The
second chapter in each section describes the spectroscopic
behavior of the functional groups, with data tables, examples,
and discussions for each. For example, in the vibrational section
it includes compact tables ordered both by functional group
and by frequency. The third chapter in each section,
"Structural/Chemical Analysis", has a discussion of the analytical
uses of the technique and includes advanced interpretation
techniques. For example, the electronic chapter describes
the Woodward rules, the octant rule, and exciton coupling.
The five NMR chapters are organized a bit differently: one
chapter is on theory, two are on spectroscopic behavior-one
for chemical shift and one for coupling constant (each for
carbon and hydrogen), and two are on analysis-one for
one-dimensional and one for two-dimensional techniques.
Peptides and nucleic acids are integrated into all sections.
Comparisons are inevitable in book reviews: in this
case, of the first collaboration of most of these authors,
Organic Structural Analysis (OSA) (1), with their second effort,
Introduction to Organic Spectroscopy (IOS)
(2), and with the popular Spectrometric Identification of Organic
Compounds (SIOC) (3). OSA provided current information about structural
techniques but had no problems; that oversight was corrected
with IOS. Organic Structural Spectroscopy provides an even
better variety of problems at the end of each chapter and 35
challenging integrated problems, all with data of consistent
and high quality. Most problems do not include solutions or
references, but the integrated problems have
clues-formulas and functional groups for each problem. Consistent with
their goal "to obtain enough such information to
overdetermine the structure" (page 5), the following are provided for
each unknown compound: CI and EI MS, 1H and
13C NMR 1D spectra (and sometimes DEPT), COSY and
HETCOR, FTIR (sometimes Raman) and UV-vis spectra
(sometimes CD or ORD). I enjoyed working the integrated problems
so much that it was hard to return to writing this review.
For the graduate student in organic chemistry,
Organic Structural Spectroscopy would be a far better choice than
SIOC. It provides a much better foundation in theory,
integrating related techniques and presenting state-of-the-art
methods, without sacrificing the detailed discussion of spectral
interpretation so necessary for routine spectral analysis.
Suggestions. Crystallography is an increasingly
important tool in organic chemistry and should be restored to the book
(it was part of OSA); organic chemists need to know enough
about it to use the results intelligently. Fluorescence and
phosphorescence are also accessible and informative and of
particular importance in bioorganic chemistry; they
could easily be included.
Literature Cited
1. Lambert, J. B.; Shurvell, H. F.; Verbit, L.; Cooks, R. G.;
Stout, G. H. Organic Structural Analysis; Macmillan: New York, 1978.
2. Lambert, J. B.; Shurvell, H. F.; Lightner, D. A.; Cooks, R.
G.; Stout, G. H. Introduction to Organic
Spectroscopy; Macmillan: New York, 1987.
3. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C.
Spectrometric Identification of Organic
Compounds, 5th ed.; Wiley: New York, 1991.
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