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Book Review Reizvolle Molekle der Organischen Chemie. (Series Teubner Studienbcher Chemie). By F. Vgtle

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new developments in techniques now necessitate an updated
treatment of the subject. The material is divided into 15
chapters which are written in the style of review papers. The
topics covered are as follows: the functional forms of
biominerals; crystallographic strategies of biomineralization; the carbonate calcification of algae, matrix-crystal interactions in CaCO, biomineralization; stereochemical and
structural relationships between macromolecules and crystals in biomineralization; in vitro studies of calcium phosphate crystallization; biochemical studies of teeth mineralization in vertebrates, chemical studies of biogenic silicates;
function and structure of ferritin and hemosiderin, biomineralization of iron in the teeth of molluscs; mineralization of
magnetite in unicellular organisms; structural and analytical
studies of metal ion-containing granules; the use of proton
beam analysis in studies of mixed biominerals; the significance of studies on biomineralizates for materials technology.
The contents are, without exception, good and the treatment of the subject matter is impeccable. For the specialist
the book offers a rich source of ideas and suggestions. However, only three of the articles are concerned with matrixcrystal interactions, which is the central topic of biomineralization. Moreover, two articles on this subject put forward
controversial views, giving the impression that the role of the
organic matrix is questionable, or at least unimportant (see
also the preface). The reader is left alone with this problem,
without being given a clear answer. Some time ago S . Munn,
in his article “Biomineralisation” (Chem. Unserer Zeit 20
(1986) 69), gave a much better, unambiguous and impressive
statement of his position on this question. There he clearly
and unequivocally explained the difference between geological minerals and biomineralizates. The fundamentals of
techniques and theory are certainly a part of this question.
Here an unusually large amount of space is devoted to these
aspects and to crystal structure studies. Moreover, of the
total of about 500 pages of text, almost 200 are devoted
solely to iron, resulting in a serious imbalance. Lengthy discussions about ferritin structures have very little to do with
biomineralization. Alongside these chapters the more biologically orientated articles give the impression of having
been grafted on. Only one page is given to pathological
biomineralization processes. However, apart from these few
inconsistencies. the book opens up some useful chemical and
biochemical perspectives.
Gottfried Krumpitz [NB 1102 IE]
Institut fur Anatomie, Physiologie und Hygiene
der Haustiere
der Universitat Bonn (FRG)
Reizvolle Molekiile der Organischen Chemie. (Series: Teubner Studienbucher Chemie). By F: Vogtle. Teubner, Stuttgart 1989. 402 pp., paperback, DM 39.80. -ISBN 3-51903503-0
Each volume in the series “Teubner Studienbucher
Chemie” deals with fundamental and more advanced aspects
of a particular field of chemistry. The books do not aim at
the breadth of coverage of a textbook, nor at the depth of
treatment of a comprehensive monograph; instead they are
intended only to give the student of chemistry an introduction
to specialized topics that are of current interest, and which
are therefore undergoing rapid development.
In the volume “Reizvolle Molecule der Organischen
Chemie” published in 1989 (and also in the following volume
Angew. Chem. In[. Ed. Engl. 30 f 19911 No. 2
8 VCH
“Supramolekulare Chemie - Eine Einfiihrung”,’*] which appeared almost simultaneously), Fritz Vogtle presents a survey of “attractive molecules” relevant to his field of study.
His starting point is a wish to open up to the reader, in a way
that is both instructive and entertaining, the great variety of
organic chemistry, by taking him or her on a journey of
discovery through the field of unusual molecules and all that
relates to them (their history, synthesis, chemical and spectroscopic properties, and applications). In the resulting thoroughly readable organic chemistry book, the appeal of the
“attractive molecules” referred to in the title is revealed not
least through the many lavish stereoscopic illustrations
which provide three-dimensional views; Vogtle’s artwork
studio has already set a high standard of quality with illustrations such as these in numerous publications. They are a
delight to the eye! Or, as the author himself puts it on page
23: not least of the aimes was that merely looking at the
structures shown here should bring joy to the heart of every
chemist!
Among the most notable of the “attractive molecules”
that Vogtle has in mind in the title of the book are hydrocarbons that are to some degree exotic. Accordingly, the introduction (19 pp.) is followed by detailed excursions into the
chemistry of interesting aliphatic hydrocarbons (Chapter 2,
56 pp.), arenes (Chapter 3, 115 pp.), and “araliphatics”
(Chapter 4, 65 pp.). It is evident that deciding what to include or leave out must have been a painful choice. Some of
the interesting molecules that were filtered out are the following: tetra-tert-butyltetrahedrane, cubane, dodecahedrane, adamantane, pagodane, and [l . l .l]propellane (Chapter 2); the triphenylcyclopropenyl cation, azulene,
biphenylene, circulene, and [7jhelicene (Chapter 3); triptycene, iptycene, 1$-methanonaphthalene, [2.2.2jcyclophane,
and superphane (Chapter 4). As one can see from the restrictions placed on the material included, no attempt has been
made in Vogtle’s book to cover the entire field of exotic
hydrocarbons. Instead, rigorously limiting the coverage to
just a ,few candidates has made enough space available to
allow a satisfying breadth and depth in the treatment of the
material.
The meticulous care that Vogtle has brought to the task of
doing justice to the title of the book is evident from the
lengths of the bibliographies to the chapters, which amount
to a total of 31 pages! In a literature study of such a high
standard as this, it is not surprising to find that only a few
years ago it would not have been possible to write this particular book, despite the fact that the topic of exotic hydrocarbons is far from new. Among the recent reactions included
are the synthesis of cubene (October 3988), Prinzhuch’s second-generation syntheses of dodecahedrane (March 1989)
and the anionic polymerization of [I. 1.1jpropellane (May
1989).
Whether one’s interest lies mainly in deeper subjects such
as a comparison of azulene syntheses, in relationships between structure and color in azulenes, in the regioselectivity
of electrophilic substitutions of biphenylenes, of 1,smethanonaphthalene or of cyclophanes, whether one wishes
to become enmeshed in the three-dimensional structural formulas of the helicenes, heterohelicenes or helicenophanes, or
goes in search of curiosities such as information about
adamantane chemistry being carried out on u tonnage scale in
Japan with the aim of treating Parkinson’s disease, or about
evidence for the presence of the cyclopropenylium ion in
Halley’s comet, Vogtle’s book offers something for everyone
who enjoys browsing among topics in organic chemistry that
[“I
Review: Angew. Chem. 102 (1990) 112.
Verlagsgesellschaft mbH, W-6940 Weinheim, 1991
0570-0833191jO202-0215S 3.50+ .25/0
21 5
are off the well-trodden track of textbooks. Moreover, the
reader who has become tired of hydrocarbons will welcome
the relief of Chapter 5 on heterocycles and compounds
with pharmacological activity, dealing with Troger’s base,
acetylsalicylic acid, vitamin B, and phthalocyanines. I n this
reviewer’s opinion the chapter might also have very usefully
combined the pharmacologically active with the exotic by
giving a glimpse into the fascinating chemistry of antitumor
antibiotics of the enediyne type (Neocarzinostatin, Esperamycin, Calichemicin), which currently are possibly the
“hottest” of all classes of biological substances.
The formula schemes are clear and visually pleasing
throughout (some minor exceptions: the undecipherable trishomocubyl moieties on page 65, the nearly invisible
C = C bonds in the intermediates 8 and 9 on page 72, and
the representation of phthalocyanine on page 332 which
seems more like a puzzle. The very small number of errors in
the structural formulas include a missing carbonyl oxygen in
8 on page 35, the omission of the second regioisomer of the
bis(diazoketone) in the formula on page 72, three missing
double bonds in 10 on page 189, and (CH,CO),O instead of
(CH,CO),O on page 293. A few of the synthesis schemes
(pages 60,72,140,174,211,268,305) could have been made
even more informative by inserting the reagents (although
these are, of course, referred to in the text).
The text is written in a flowing style, and covers the subject
matter with a breadth and depth that are appropriate to the
book. The few minor errors are unlikely to lead the reader
astray; for example, HCI elimination reactions are described
as being base-catalyzed instead of being carried out with
stoichiometric quantities of base (pp. 86, 87), “Retro-AlderReaktion” appears instead of Retro-Aldol-Reaktion (p. 51),
and reference is made to planar conformation instead of
configuration (p. 67). On page 61 the Wagner-Meerwein rearrangement does not start out from the adamantyl cation
but leads to it. On page 72 the word “Diazotierung” is used
to describe the transfer of a diazo group, and on page 122 an
azo coupling reaction is wrongly described by the word
“Azotierung”. “Benzofulvalen” on page 100 should read
Benzofulven, on page 264 “o-Xylen” appears instead of oXylylen, on page 266 “Propionsaureester” instead of Propiolslureester, and on page 269 “Ethyldiazotat” instead of
Ethyldiazoacetate. On page 218 it is evident from the struc-
tural formula that a “Carbeniat” here means a carbanion.
The NMR spectrum described on page 136 is of the AA‘BB’
type, not A,B,. In the chapter on azulenes Figures 7 and 9
show the formulas of intermediates in reactions that are
probably better described as concerted processes (an electrocyclic ring-opening and a [2 + 81-cycloaddition). Occasionally the term mesomerism is used in an unfortunate way
which could lead to confusion for beginners in organic chemistry. References such as those to “EinfluS hyperkonjugativer Grenzformen” (effects of hyperconjugated canonical
forms, p. 66), or to discontinuance of a “Moglichkeit zur
Ausbildung mesomerer Grenzformen” (possibility of formation of mesomeric canonical forms, p. 126), the showing of a
mesomerism arrow between structural isomers (p. 130), or
the analysis of the possible canonical structures for a carbenium transition state (p. 137) imply a degree of reality for
canonical forms which is of questionable validity.
The preface contains an assurance that large portions of
the book assume only knowledge of an undergraduate level,
but perhaps one should not take this quite literally. In fact,
in many parts of the book the treatment is of a breadth and
depth (as already commended above) such that only very
advanced undergraduate or rather graduate students are
likely to benefit from reading “Reizvolle Molekiile”. However, those at the latter stage of their studies who wish to gain
a deeper knowledge of organic chemistry through reading of
a less formal kind are assured that, by buying Vijgtle’s book,
they will obtain pleasure from it without undue pain (at a
price of only DM 39.80 for 402 pages).
Reinhard Briickner [NB 1091 IE]
Fachbereich Chemie
der Universitat Marburg (FRG)
Corrigendum
The address of the authors of the communication “Dynamic
HPLC: A Method for Determining Rate Constants, Energy
Barriers, and Equilibrium Constants of Molecular Dynamic
Processes” (Angew. Chem. Znt. Ed. Engl. 30 (1991) 74) should
read :
Dr. J. Veciana, Dipl.-Eng. Chem. M. I. Crespo
Institut de Ciencies de Materials - C.I.D., C.S.I.C.
Jordi Girona, 18-26, E-08034 Barcelona (Spain)
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