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Book Review Cyclophanes Vols. 1 and 2. Edited by P. M. Keehn and S. M

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[2] R. Burns, J. Corbett, Inorg. Chem. 20 (1981) 4433; crypt=
4,7,13, I6,2 I ,24-hexaoxa-I , 1O-diazabicyclo[8.8.8]hexacosane.
[31 Calcd. for C64H144N4H&Te12:
C 23.26, H 4.36, N 1.70, Hg 24.29, Te
46.3X0h; found: C 23 75, H 4.78, N 1.89, Hg 24.12, Te 45.83%.
(41 Crystal data for 1 : Monoclinic, space group P2,/n, u = 1665.3(6),
b=2688.8(6), c=2706.8(6) pm, ,9=90.72(3)” at 2O”C, Z = 2 , MoKo
(d=71.07 pm), R=0.057 for 2207 reflections, solved by direct methods.-2: monoclinic, P2,, u = 1040.0(2), h=1732.4(4), c = 1374.2(3) pm,
D=94.02O, 2 0 ° C MOK- (A=71.07 pm), R=0.057, 3939 reflections.Further details of the crystal structure investigations are available on request from the Fachinformationszentrum Energie Physik Mathematik,
D-75 14 Eggenstein-Leopoidshafen 2 (FRG), on quoting the depository
number CSD 51 287, the name of the author, and the full citation of
the journal.
[5] J . Waser, L. Pauling, J . Chem. Phys. 18 (1950) 747.
161 B. Eisenmann, H. Schwerer, H. Schafer, Mar. Res. Bull. 19 (1984) 293.
171 B. Eisenmann, H. Schwerer, H. Schafer, Muter. Res. Bull. 79 (1984)
1 189.
[S] B. Eisenmann, H. Scrod. H. Schafer, Muter. Res. Bull. 19 (1984) 293.
191 P. Bottcher, U. Krestchmann, J. Less-Common Met. 95 (1983) 81.
110) P. Bottcher, U. Krestchmann, 2. Anorg. ANg. Chern. 491 (1982) 39.
1111 R. Fenn, J. Oldham, D. Phillips, Nature (London) 198 (1963) 381.
[I21 K. Aurivillins, C. Stalhandske, Actu Crystullogr 8 3 0 (1974) 1907.
Cyclophanes, Vols. 1 and 2. Edited by P. M . Keehn and S.
M . Rosenfeld, Academic Press, New York 1983. Vol. I :
xxx, p. 1-358, bound, $65.00, ISBN 0-12-403001-7/Vol.
2: xxx, p. 359-725, bound, $ 60.00, ISBN 0-12-4030025.
This set appears as part of the excellent series of monographs chosen by its editor H . H. Wasserman. There may
be an embarras de richesse in updating reviews of the
chemistry of cyclophanes (a series edited by F. Vogtle comprising two volumes, albeit smaller, has recently appeared)
but the present set is more encyclopedic.
The editors have done a fine job in choosing authors
and in parcelling out the vast material to be covered. Inevitably there is some overlap but this is surprisingly minimal.
I agree with the editors’ claim that each chapter stands on
its own. The set opens with a charming chapter by the father of the field; Don Cram’s personal account is a short
overview, past, present, and future. The other chapters
either emphasize synthesis and reactions, or properties and
structure, or, in the best ones, there is a blend of the two.
The more synthetic chapters are by Rosenfeld and Chloe
([n]cyclophanes, 46 pages), Reiss (condensed cyclophanes,
41 pages). Hopf (multibridged cyclophanes, 51 pages), Misumi (multilayered cyclophanes, 55 pages). Those emphasizing properties and structure are by Liebmnn (the conceptual chemistry of cyclophanes, 45 pages), Keehn (the
crystal structure of cyclophanes, 169 pages), Mitchell
(NMR properties and conformational behavior of cyclophanes, 71 pages). The chapters that, to my taste, blend all
aspects and are thus the most useful in giving the reader an
overall review before consulting the primary literature are
those by Paudler and Bezoari (synthesis and properties of
heterophanes, 82 pages) and It6, Fujise, and Fukuzawa
(non-benzenoid cyclophanes, 35 pages). Biological applications are given in two chapters by Odashima and Koga
(cyclophanes in host-guest chemistry, 49 pages), and by
Sutherland (cyclophanes as synthetic analogs of enzymes
and receptors, 46 pages). The first doesn’t touch upon, the
second emphasizes crown ether hosts.
I have a bone to pick with Don Cram’s statement: “It
seems that the selection of certain research problems is
dominated by a subliminal aesthetic judgment.” Subliminal indeed! There is little doubt that symmetry motivates
many chemists in their choice of subject, in full awareness,
Liebman’s excellent chapter covers chemical concepts
which have been clarified through cyclophane chemistry.
Angew. Chem. Int. Ed. Engl. 24 (198.7) No. 5
Keehn’s very useful chapter includes a wealth of structural
information accompanied by general explanatory comments. Mitchell’s chapter is not as exhaustive but clearly
shows how NMR techniques have been used to assign rigid stereochemistry or conformation in mobile systems.
Rosenfeld and Chloe include the variegated approaches for
synthesis of [n]cyclophanes. Paudler and Bezoari do a good
job in covering all aspects of heterophane chemistry but
Reiss covers only synthesis of condensed benzenoid cyclophanes. Although he mentions in telegraphic style, e.g.,
that electronic spectra have been measured, his omission
of more detail gives short shrift to important aspects of the
work of Sraab and his group. On the other hand, the It6 et
al. chapter, albeit shorter, covers non-benzenoid cyclophanes in a much better way following Hamlet’s invocation: “There are more things in heaven and earth, Horatio,
than are dreamt of in your philosophy.” Reiss can learn
from this. Hopf s chapter, though essentially synthetic, is a
gem in its general approach and pedagogic clarity. Misumi’s chapter covers his subject’s manifold aspects. Both
biochemical chapters are excellent, well-coordinated reviews with no unnecessary overlap between them.
Many of the authors (and the editors who did not correct them) d o not know that one converts 52 into 51, not
to 51. It is amusing to note that the Japanese authors (or
those who do not describe synthetic steps) do not err in
this respect; they do not use the word in their constructions.
This set on cyclophanes is a must in every library; even
those suffering from the steep rise in Journal prices would
be well advised to buy them, as would all wealthy individuals interested in the subject.
David Ginsburg [NB 667 IE]
Technion-Israel Institute of Technology, Haifa
Chemical Dynamics via Molecular Beam and Laser Techniques. By R . B . Bernstein. Oxford University Press, Oxford 1982. ix, 362 pp, paperback, E 10.95.
This book is based on the Hinshelwood lecture series
delivered by the author in Oxford in 1980. An introductory
discussion of problems of reaction dynamics is followed
by treatment of the following topics: The connection between reaction cross section and rate constant, the principle of microscopic reversibility, jet stream properties,
43 5
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