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Book Review Fluorine Chemistry. Vol. V. Edited by J. H. Simons

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Physical Methods in Heterocyclic Chemistry. Edited by A . R.
Katritzky. Vol. I: Nonspectroscopic Methods. Vol. I1 :
Spectroscopic Methods. Academic Press Inc., New York
1963. 1st edit., Vol. I: XI + 346 pp., numerous tables, linen
$ 12.-. Vol. I I : XI f 398 pp., numerous figs. and tables,
linen $ 14.-.
It is the aim of this two-volume work to single out the
application of the most important physical methods to the
chemistry of heterocyclics and to summarize the literature o n
this subject. The following topics are discussed: in Vol. I:
ionization constants (A. Albert), heteroaromatic reactivity,
with a section on molecular-orbital calculations (J. Ridd),
X-ray diffraction by heterocycles ( W . Cochran), solubilities
of heterocyclic compounds ( W. Pfeiderer), dipole moments
in heterocyclic systems ( S . Walker), and electrochemical
properties in solutions (J. Volke); in Vol. 11: electronic
absorption spectra (S. F. Mason), nuclear quadrupole
resonance ( E . A. C . Lucken), nuclear magnetic resonance
spectra ( R . F. M . White), and infrared spectra ( A . R. Katritzky and A. P. Ambler). As the titles of the chapters
indicate, the selection of topics is somewhat random and by
n o means comprehensive. Some cnapters are somewhat beyond the general topic of the book.
Each chapter begins with a short, usually clear review of the
principle of the specific method in question. This is followed
by more or less detailed indications of its use in heterocyclic
chemistry. The style of the individual chapters varies from
author t o author. Sometimes the treatment is superficial, but
other chapters are very extensive and attack the subject
matter with great thoroughness. On the whole, the books
represent more a series of essays than a well rounded-off
work, but the variety of their subject matter and their
numerous references (literature up to the start of 1962) provide
many a n incentive not only to the specialist in the field of
K. Dimroth
[NB 352/210 IE]
Fluorine Chemistry. Vol. 111: Biological Effects of Organic
Fluorides. By H . C . Hodge, F. A . Smith, and P . S. Chen.
Edited by J. H . Simons. Academic Press, New York-London 1963. 1st edit., XI
240 pp., 7 figs., 34 tables, linen
$ lo.-.
The chemistry of organic fluorine compounds has developed
rapidly since 1945. Fluorinated organic compounds are being
used more and more as solvents, plastics, dyestuffs, and
pharmaceuticals. Since the discovery of the high toxicity of
fluoroacetate, the biological properties of organofluorine
compounds have become part of the realm of toxicologists
and biochemists. I t is therefore a laudable enterprise that
the authors have undertaken here in critically reviewing
about 1600 publications which have appeared until 1961. The
biological properties of fluoroacetate, fluorophosphoric acid
derivatives, aliphatic fluoro compounds which may be used
as solvents or working gases, and fluorinated pharmaceutical
preparations are described o n 54 pages. The metabolism of
fluoroacetate is discussed critically and with reserve. The
influence of organofluorine compounds on enzyme systems,
microorganisms, viruses, and insects also receives mention.
Next follow 130 pages of tables. The large number of articles
to be evaluated makes any attempt at comprehensive treatment too difficult. I t is therefore not surprising that the
reviewer remarked the omission of some articles on enzyme
inhibition with fluorine-substituted organic enzyme substrates. The authors have placed the main accent o n toxiH. Machleidt [NB 3491207 IE]
cological aspects.
Fluorine Chemistry. Vol. V. Edited by J. H. Simons. Academic
Press, New York-London 1964. 1st Edit., X V + 505 pp.,
89 figures, 80 tables, linen, $16.50.
So far, Volumes I, 11, 111, and V of the series o n “Fluorine
Chemistry” started in 1950 are now available; Volume IV is
still in preparation.
Angew. Chem. internat. Edit. 1 Vol. 4(1965)
1 No. 7
The first chapter of Volume V, which appeared in 1964, deals
with the compounds of fluorine with other elements, including
the actinides, but does not describe the inert gas fluorides,
which have apparently become known only too recently. With
this review, the corresponding twelve sections of Volumes I
and I1 have been repeated in a highly condensed form and
supplemented, particularly by preparative results obtained
within the past two decades. In the second chapter, the physicochemical properties - mainly thermodynamic data - of
carbon/fluorine compounds are collected and compared
among themselves and with those of analogous hydrocarbons
and chlorocarbons. This chapter supplements the discussion
of preparative results in earlier volumes. The third section is
devoted to the nuclear chemistry of fluorine, the production
of radioactive fluorine isotopes, and their use as tracers in
chemistry and biology. Also the radiation chemistry of fluorine compounds, particularly the influence of short-wave radiation on polymeric fluorocarbons, is dealt with.
In the final chapter, for the first time in the series, the applications of fluorine and its compounds in industry and technology are discussed. It is apparently assumed that the technology and use of inorganic fluorine compounds are familiar
to the reader; the technical applications of hydrogen fluoride,
boron trifluoride, and sulfur hexafluoride are only touched
upon briefly, and it is only the application of fluorine and of
some fluorine compounds as rocket fuels that receives extensive treatment. The main accent of this chapter lies on the
multifarious uses of organic fluorine compounds, e. g. as
refrigerants, fire-extinguishers, lubricant and aerosol solvents, dielectrics, plastics, and elastomers, and as surfactants in galvanizing and in the leather and paper industries
for making products hydrophobic and oleophobic. Their
increasing use as foaming agents for making foam rubber and
plastics is not mentioned.
Thus, Volume V gives a comprehensive review of the present
status of fluorine chemistry and at the same time recapitulates
briefly the contents of the previous volumes.
H. Jonas [NB 3421199 IE]
Progress in Organic Chemistry. Vol. 6 . Edited by J. W. Cook
and W . Carruthers. Butterworths Scientific Publications,
London 1964. 1st edit., VII + 256 pp., several figs. and
tables, linen €2.17.6 (about $ 8.-).
As usual, the latest volume of this series brings progress
reports from the pens of competent authorities. In the first
chapter, E. Haslam and R. D . Haworth review the current
status of research in the field of “Vegetable Tannins”. In
the second chapter, M. F. Grundon describes the interesting
class of compounds of the “Bisbenzylisoquinoline Alkaloids”.
Structural elucidations, syntheses, stereochemistry, and biosynthesis are given particular attention. “Polyacetylenes and
Related Compounds in Nature” and the biogenetic relationships between these compounds are discussed by J . D .
Bu’Lock. W . Schafer reviews the present situation of the
“Chemistry of Phenoxazones” in the fourth chapter. Interest
in this ring system has been augmented by the isolation and
elucidation of the structures of the ommochromes, actinomycin,and the orceine dyestuffs.The next chapter on “Carbenes”
by W. Kirmse gives a n excellent review of the turbulent
developments in this field of organic chemistry. In the final
chapter, S . F. Mason demonstrates with examples the application of the molecular orbital theory to reaction equilibria
and rate constants.
Progress reports by acknowledged experts, such as appear
in so attractive a mixture in the present volume, are becoming more and more important in view of the ever increasing gush of articles flooding the chemical literature.
Like its predecessors, the new volume of this series therefore
represents a veritable embellishment of the chemical literature.
However, it would have been useful for the reader if some
indication were given of the date up to which the literature
was reviewed for the individual topics.
H. Stetfer
[NB 355/213 IEJ
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