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Book Review Analytical Artifacts GC MS HPLC TLC and PC. (Journal of Chromatography Library Vol. 44). Edited by B. S

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as the dating of geological specimens using the radioactive
decay of lead isotopes. Back once more in Copenhagen, he
invented neutron activation analysis with Hilde Levi, then
became increasingly involved in the applications of artificial
radioactive isotopes in biology and medicine, initially using
32P; from this work nuclear medicine developed. For his
research on isotopes as tracers for investigating chemical
reactions he received the Nobel Prize for Chemistry in 1943.
The lectures were linked under the general heading “Interdisciplinary Applications of Nuclear Methods”. Only the
first of these relates directly to Heves.~;in this Gustrlf‘Arrhenius and Hilde Levi give a review of his geochemical and
cosmochemical period from 1922 to 1935 (26 pp.). Rudolf
MijJkiuer describes the beginnings of the precision gammaray spectroscopy technique which is named after him
( I 3 pp.). and following this Vitulii Goldanskii then discusses
the method in greater detail. using examples of applications,
mainly in the field of biomacromolecules (35 pp.). Next
comes a contribution by Ferenc M t w i on the neutron spinecho technique, again applied mainly to biomolecules; here
an important field of research which originated at the place
of the meeting was described (1 1 pp.). The book ends with a
detailed review by Kai Sieghahn of the development and still
continuing refinement of the ESCA (electron spectroscopy
for chemical analysis) method (37 pp.).
This little book will be mainly useful to readers who are
engaged in work in the fields dealt with in the individual
papers. It should also be in every department library, as a
way of keeping alive the memory of Grorg von Hevesy, a
gentleman scientist who had the resources to enable him to
work for a considerable time without a salary, and thus to
remain literally his own boss. There is something in the view
which is occasionally put forward that the decline of science
in this country began with the disappearance of the wealthy
“Privatdozenten”, for these people were truly independent.
Ciinter Herrmann [NB 990 IE]
Institut fur Kernchemie
der Universitgt Mainz (FRG)
Carbocycle Construction in Terpene Synthesis. By Tse-Lok
Ho. VCH Verlagsgesellschaft, Weinheim/VCH Publishers,
New York 1988. xiv, 768pp.. hard cover, D M
260.00. - ISBN 3-527-26582-1 10-89573-279-3
This book by Ho o n ring-forming reactions in terpene
synthesis is a long one. It has 760 pages, 1600 references and
about 7000 structural formulas which are correctly drawn in
nearly every case. What does the book offer the reader that
is new? No places the ring-forming reaction as the central
step in every synthesis, with the synthesis proceeding around
it, before it and following it. This viewpoint strikes the reviewer as misleading, or at least biased. It can sometimes be
appropriate, as in some of the more spectacular cationic
cyclizations, e.g. in the synthesis of alnusenone (page 290),
but it is an overstatement in many cases, especially for syntheses of which ring formation is a comparatively insignificant part, e.g. the formation of the second cyclopentane ring
in the synthesis of pentalenolactone (page 92). This overemphasis on ring formation is reminiscent of total syntheses of
natural products in which, say, 15 laborious stages are needed to prepare the precursor for the ingenious one-stage ringclosing reaction.
The book treats the subject defined above in 11 chapters:
Robinson annelations, aldol condensations, Michael aldol
condensations, Claisen and Dieckmann reactions, in-
tramolecular alkylations, cationic cyclizations, Diels-Alder
reactions, other thermal processes (i.e. [3 + 21-, [4 31-additions, etc., Wittig and Claisen rearrangements, electrocyclizations, etc.), free radical cyclizations, small ring syntheses
(Simmons-Smith reaction, carbene chemistry, photochemical formation of cyclobutane, etc.), ring enlarging and ring
contraction reactions. and a chapter on “transitory” ring
formation reactions, i.e. those that subsequently serve other
purposes, e.g. cyclopropane + gem-dimethyl.
The book also takes into account the most recent published work. Even the main text contains quite a number of
1987 references. while the 50 or so references contained in the
appendix are mainly to papers published in 1988.
Unfortunately the information content of the reaction
schemes is very scanty. Only for the centrally placed ringforming reaction are some details of the reactants rather
casually included, and even here without giving yields. More
information here would have been very useful for quick reference, and rapid access to information is without doubt one
of the main purposes of such a book.
The content of the book overlaps to a large extent with the
chapters on mono-, sesqui- and triterpenes in the series “The
Total Synthesis of Natural Products” by ApSimon. While
it is true that H o is seven to eight years more up-to-date.
ApSirnon is better in information content and clarity.
Finally, a few errors will be mentioned, more in order to
show that the reviewer has read the hook carefully than by
way of serious criticism. On page 481 a CH, group is missing
from the route to nootkatone, on page 335 E/Z-ocimenone
was converted using isoprene, not ocimene, and the relevant
reference is Adams (1975), not Ayar (1973. 1975). On page
215 the CH, and ClCH, groups are shown in the wrong
positions in the ishwarone synthesis. But, as has already been
said, these are unimportant details in a work such as this.
To summarize, the book constitutes a new attempt at presenting the formidable variety of terpene syntheses according to a different method of classification based on their
ring-forming reactions. Since every such new approach offers the possibility that in thumbing through the book one
can learn something new, or see something which is already
familiar from a different viewpoint, it is a useful book for the
synthetic chemist and, although rather expensive, is worth
buying.
Georg Frater [NB 966 IE]
Givaudan Forschungsgesellschaft AG
Dubendorf (Switzerland)
+
Analytical Artifacts: GC, MS, HPLC, TLC and PC. (Journal
of Chromatography Library, Vol. 44). Edited by B. S.
Middlediitclz. Elsevier, Amsterdam 1989. 1033 pp., hard
cover, HFI 495.00. -ISBN 0-444-871 58-6
Every honest analyst has at some time detected in his
samples substances whose presence has a t first seemed astonishing. In many cases it turns out, after further careful investigation, that these have found their way into the analytical
samples in mysterious ways, through the operation of
“Murphy’s Law”, during some purification or sample preparation step, or even during sampling. In publications mention of such occurrences is either shyly omitted, since no one
willingly admits to having been stupid, or hidden away in
incidental minor comments. After all, why not let others
make the same mistakes?
It is surprising, therefore, that despite this there are so
many wrong chromatographic interpretations to he found in
the literature; in this work they are systematically collected
together in more than 1000 pages. In each case the pitfalls are
described and listed under either the name of the wrongly
identified substance or that which was responsible for introducing them. For example, under the keyword “Tenax”,
which is a polymer often used for concentrating trace organic
impurities present in the atmosphere, are listed more than 40
compounds and compound classes that have allegedly been
found in environmental samples, but which originated from
the polymer itself. Perhaps it is already sufficiently well
known that samples purified by gas chromatography or in
reverse phase columns can be contaminated with siloxanes,
but the fact that difficulties can arise with chromatographic
tests for drugs, as used in the USA, if one has been eating
poppy-seed bread rolls, not only illustrates the sensitivity of
the chromatographic test method, but also emphasizes the
need for care in interpreting analytical results.
Under the keyword “filter paper” are listed over 60 compounds, from simple hydrocarbons to steroids. which have
been introduced during filtration. The book is enriched by
many practical hints, ranging from sample injection procedures to the problems encountered in the determination of
nitrosamines, and precautions against both false positive
and false negative results in this case. There are also historical anecdotes concerning false analyses (e.g. the poisoning of
Napokon by arsenic, or the theory that the Philadelphia
legionnaires were poisoned by tetracarbonylnickel, which
arose because the samples were contaminated by nickel from
a spatula), which enliven the book.
In addition to keywords of a general type, all the compounds identified as artefacts are listed alphabetically. In
addition to the molecular formula, molecular mass, trivial
and systematic names, and CAS and Merck index numbers,
the compilation also includes mass spectra in many cases.
Also provided are detailed descriptions (with literature references) of how and where the substance appeared as an artefact, and precautions that were taken to avoid errors. In
addition to the usual index of compounds, the mdSS spectrometric data (base peak and 2nd and 3rd peaks) are also
indexed in such a way that the corresponding substance can
be quickly found.
Despite the relatively high price of HF1495.00, this book
should be regarded as essential reading for everyone seriously engaged in chromatographic trace analysis. The price is
small when compared with the trouble, annoyance and expense caused by incorrect analyses.
Heinz Engelhardt [NB 983 IE]
Institut fur Physikalische Chemie
der Universitlt Saarbriicken (FRG)
Name Reactions and Reagents in Organic Synthesis. By E. P.
Mundy and M . G. Ellerd. Wiley, Chichester 1988. ix,
546 pp., hard cover, L 27.05. -ISBN 0-471-83626-5
This is neither an ordinary book nor a systematic encyclopedia; rather it is a well-ordered card index that has been put
between covers. The following layout is repeated 120- 130
times on the left-hand pages: a first section consisting of the
named reaction with an equation, a mechanism, and coniments on its applicability; a second section containing
reagents with their formulas, areas of application and methods of preparation, followed by about five literature references. On the right-hand page in each case are about five
examples (in large print) of reactions taken from the papers
cited.
1538
(y) YCH Verla~.~ge.~ellsrhafi
mhH. D-6940 Weinheim, 1989
The following are two examples: 1) Vilsmeier reactions tor
the regioselective formylation of an open-chain triene and
for preparing selenoaldehydes are described. N o yield is given for the first reaction (are the other isomers also formed?);
the second reaction means nothing to me in the absence of
any discussion of selenoaldehydes. The three other Vilsmeier
reactions cited are of “normal” types, and can also be found
in standard textbooks. 2) The most common application of
Mitsonubu’s reagent is for OH-substitution in alcohols with
a change of configuration. Here one also finds the esterification of carbon dioxide using pentanol. This is certainly
surprising, but what purpose does this serve in organic synthesis? (see the book’s title). The examples throughout are
either very familiar or very exotic. There are so few surprises
in the information given (see, for example, under the keywords formic acid and potassium hydride) that one shrugs
one’s shoulders and dismisses it as inconsequential. There is,
moreover, no index of reaction types, and consequently it is
not possible to search for particular ones.
The never-failing references to pages in March’s “Advanced Organic Chemistry” and Fieser’s “Reagents for Organic Synthesis” are evidence of painstaking student work.
Basically the book is nothing more than this. None of the
material has been treated in a novel way or freshly evaluated;
instead it has merely been collected together and, on the
whole. Faithfully reproduced (an exception is the incorrectly
shown bonding in the chair form of cyclohexane, e.g. on
page 477). To misquote Arno Schmidt, the book remains a
Zettel-Alptraum (card-index nightmare). Throughout the
whole of the five hundred-odd large-format pages the same
question keeps coming to mind: what is it meant to be?
Jiirgen-Hinrich Fuhrhop [NB 986 IE]
Institut fur Organische Chemie
der Freien Universitat Berlin
Mechanistic Principles of Enzyme Activity. Edited by J. E:
Liebrnan and A . Greenberg. VCH Verlagsgesellschaft,
Weinheim/VCH Publishers, New York 1988.404 pp., hard
cover, D M 204.00. -ISBN 3-527-26907-X/0-89573-706-X
The field of enzyme chemistry has undergone a significant
mutation over the last ten years thanks to advances in cognate biological technologies and in instrumentation. As a
result, the focus of attention has broadened from the substrate and mechanisms of chemical catalysis to include detailed consideration of the properties of the protein relevant
to catalysis. To reflect such a change in emphasis in the
title of a multi-author book is extremely difficult and the
Familiar ring of many of the chapter titles also disguises
the high scientific and intellectual content of many of the
chapters.
We are dealing here with a book that not only presents the
information currently available on several important topics
but also shows how ideas have developed, identifies problems in current understanding, and indicates potential lines
for future research. Further, where appropriate, there is a
concise exposition of the theory relevant to the understanding of the problem, for example in the discussion of electron
transfer in cytochromes (Dixon).Several other chapters deal
with specific classes of enzymes including peptidases (zinc
proteases, Christianson and Lipscomb; serine proteases.
Schoiven) and oxidases (hemoproteins, Bruice; flavin mixed
function oxidases, Bruice; glutathione dependent aldehyde
oxidation, Creighton and Pourtornabbed). Two others of general significance discuss stereoelectronic analysis (Eenner)
0570-0833!89ilt 11-1538 S 02.50!0
Angew. Chem. Ini. Ed. EngI. 28 (1989) No. I I
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