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Book Review Organic Chemistry The Name Game. Modern Coined Terms and Their Origins. By A. Nickon and E. F. Silversmith

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the structure of organic compounds is thus considerably
simplified,“’] and all the more so in practice, since seldom
are all C,C couplings needed but only must be proven for
a few C atoms.
Received: April 5, 1988;
revised: May 30, 1988 [Z 2688 IE]
German version: Angew. Chem. 100 (1988) 1198
CAS Registry number:
1, 71-23-8.
[I] A. Bax, R. Freeman, S. P. Kempsell, J. A m . Chem. SOC. 102 (1980)
4849.
[2] A. Bax, R. Freeman, T. A. Frenkiel, M. H. Levitt, J . M a p . Reson. 43
(1981) 478; T. H. Mareci, R. Freeman, ?bid.48 (1982) 158.
131 Review: J. Buddrus, H. Bauer, Angew. Chem. 99 (1987) 642; Angew.
Chem lnr. Ed. Engl. 26 (1987) 625.
141 S. Berger, Org. Magn. Reson. 22 (1984) 47.
[S] S. Berger, K. P. Zeller, J. Org. Chem. 49 (1984) 3725.
161 0 . W. Sorensen, R. Freeman, T. A. Frenkiel, T. H. Mareci, R. Schuck, J
Mogn Reson. 46 (1982) 180.
171 S. W. Sparks, P. D. Ellis, J. Magn. Reson. 62 (1985) 1.
IS] P. J. Keller, K. E. Vogele, J. M a p . Reson. 68 (1986) 389.
[9] H. Kessler, H. Oschkinat, C. Griesinger, W. Bermel, J. Magn. Reson. 70
(1 986) 106.
[I01 S. Davies, J . Friedrich, R. Freeman, J. Magn. Reson. 75 (1987) 540.
[ I l l J. Brondeau, C . Millot, D. Canet, J. M a p . Reson. 57 (1984) 319.
[I21 D. Canet, J. Brondeau, J. C. Boubel, A. Retournard, Magn. Reson.
Chem. 25 (1987) 798.
[I31 P. J. Hore, E. R. P. Zuiderweg, K. Nicolay, K. Dijkstra, R. Kaptein, J.
A m . Chem. SOC.104 (1982) 4286; P. J. Hore, R. M. Scheek, A. Volbeda,
R. Kaptein, 3. Magn. Reson. 50 (1982) 328.
1141 S. Berger, J. Chem. SOC.Chem. Commun. 1984. 1252.
[I51 S. Berger, J. Magn. Reson. 66 (1986) 555.
[I61 Experimenfal: 5-mm NMR tubes with 20% solution of n-propanol in
CDCI,, 303 K. Bruker AM400 N M R spectrometer with Aspect 3000
process computer and selective irradiation unit SEU. 90” pulse PI
6.3 ps, selective 90” pulse P3 20 ms, gauss shape. Traces b, c and d in
each case 512 pulse sequences, spectral width 12000 Hz, 64 K data
points, D2 = 7.5 ms, D3 = 3 ps, acquisition time AQ relaxation delay
D1=5s.
[I71 The principle presented here has in the meantime been extended to the
inverse detection of C,H correlations: S . Berger, J. Magn. Reson.. in
press.
+
BOOK R E V I E W S
Organic Chemistry: The Name Game. Modern Coined
Terms and Their Origins. By A . Nickon and E. F. Siluersmith. Pergamon Press, Oxford 1987. xii, 347 pp., bound,
L 45.00.-1SBN 0-08-035157-3; paperback, L 18.00.ISBN 0-08-034481-X
Named reactions are a time honored and useful feature
of chemical literature and communication; the custom of
name-dropping is at least equally old, even though it
usually fails to produce the intended effect. But a name
game?-or, more exactly, “Organic Chemistry: The Name
Game”, to give the recently published monograph by Alex
Nickon and Ernest F. Silversmith its full title. Can the serious and sober discipline of organic chemistry be a game
with words? This, and much more besides, is the theme of
“The Name Game”. The book, generously illustrated with
excellent structural formulas, reaction schemes and other
diagrams, is in the first place a collection of modern trivial
names and accounts of how they originated. Developed
out of a student project aimed at discovering the origins of
a wide variety of expressions, the authors have based the
compendium not only on an intensive study of the literature, but also on innumerable personal contacts over a period of about ten years. To limit the size of the compilation, the naming of natural products, and commercial
product and brand names, are dealt with only briefly; the
result is not a comprehensive index of trivial names, but
instead a real book, for both serious reading and browsing.
And no matter where one dips into it, fascination quickly
takes hold, and one becomes absorbed in reading. To appreciate this even more fully, imagine for a moment the
effect if a work of a similar kind had instead been produced in an (admittedly more comprehensive) “electronic
version”!
What, then, are the origins of the names given to the
many organic compounds prepared for the first time during recent years, and to newly discovered reactions? Who
or what agency first coined these names, what prompted
Angew. Chem Int. Ed. Engl. 27 (1988) No. 9
this, and what are their etymologies? Answer: the names
are as varied as are the people involved in chemistry, and
they reflect the personal qualities and idiosyncracies of
their creators: their sense of humor (or lack of it), their
vanities, their education (or its shortcomings), their knowledge of the world, o r their provincialism. Nevertheless, as
the authors show in the 20 chapters and six appendices of
the book, it is possible to recognize certain common features and families of words and names, which together illustrate the rather childlike pleasure that chemists take in
naming the objects resulting from their work. There i s an
abundance of names of animals; articles of apparel-especially head coverings-provide inspiration; names that
clearly have their origins in children’s toys, and which
grown-ups (?) now have, are widespread, some of the most
popular being building bricks, water-wheels and airplanes.
Foodstuffs play a role to some extent. Above all, containers of every kind have a great fascination-objects into
which things can be put. In due course we leave the household behind, and travel through cities and across national
frontiers, even as far as the stars. In short, nothing escapes
being used to form names, and inexorably there comes into
being at the molecular level a more and more fully equipped micro-universe.
Furthermore, “The Name Game” shows that the number of trivial names has grown alarmingly just in recent
times (and consequently the book is also very useful as a
dictionary, despite the limitation on size mentioned earlier). One possible cause for this is that the standard language, i.e. the IUPAC nomenclature rules, cannot keep
pace with the complexity of the structures which have been
analyzed and/or synthesized. Another factor is the notorious inadequacy of this nomenclature system for describing the dynamics of chemical reactions. New developments are essential here if we are to avoid becoming completely entangled in our own special jargon. It is conceivable, for example, that for “supermolecules” (cage structures of all kinds, layered molecules) a method of nornen1197
clature related to that for peptides might be used, in which
the building units would be represented only by initial letters (although, of course, the problems of “branching” and
“crosslinking” in the primary structures of peptides are
much simpler).
Thus it can be seen that what initially at times appeared
to be a collection of curiosities, even including trivia (although, just as beauty is in the eye of the beholder, so presumably the music of a name is in the ear of the listener),
has now raised important and far-reaching questions. For
this reason the book is also a stimulating, and often
thought-provoking, contribution to the study of the language of chemistry.
The authors too must have been well aware of this aspect of the book, since some of the appendices are only
meaningful in that light. Once one begins to consider the
words and their meanings, one progresses very quickly
from the hundredth to the thousandth. What are the origins of the expressions familiar to us? Do these wordsoften derived from Latin or Greek-sound better to our
ears (more “euphonic”) than the modern names which
have been coined, sometimes making the reader or listener
flinch? (on the lines of, for example, betweenanene, buckminsterfullerene-or better still, buckyball-and what if
barrelene had instead been named zimmerene!). The
mechanisms of (modern) word construction are by no
means new. It was already common to make up composite
words (acetal = acetaldehyde
alcohol; carbazole =
carb + az
ole); or as an extreme example, chloramphenicol-see the book for its derivation), to use abbreviations
(phthalic acid is actually (na)phthal(en)ic acid), and to
make transpositions (ninhydrin from hydrindene). On the
other hand, the making u p of acronyms, following the
modern craze for abbreviations, has recently grown to such
an extent that already one can almost begin to talk in terms
of a third generation of nomenclature. However, Appendix
A is a mine of information on explanations and derivations of standard expressions used in organic chemistry.
It would no more be possible to translate the whole of
“The Name Game” into another language than to retain
its rhyming title. This is firstly because the English language, with its great differences between the spoken and
written forms, lends itself much more readily to plays on
words than, for example, German, and secondly because
of the authors’ frequent clever and imaginative use of such
devices. Some nice examples are the following: “The vitamin C story began with ‘ignose’ and ‘godnose’. Where will
it end? Who knows?”; or: “Through deals made by Alde r . . .”; or: “Atrane is not something we board at a railroad
station”. The text abounds with puns of this sort, which,
like the anecdotes, are not only intended to cause a quick
smile, but are also very instructive. It is certainly true that
wit or fun often lead to a much quicker and better remembered understanding of a point than does a long-winded
explanation. English-speaking authors-not only when
preparing textbooks o r papers, but also when giving afterdinner talks (from whence, incidentally, an appreciable
number of the examples in “The Name Game” seem to
have originated)-use this technique more often and adeptly than we German speakers. As a general principle,
when the words of one language can no longer be translated into another, this is evidence of the vitality of both
words and language. One is then forced to adopt the foreign words-or remain silent.
As every competitor knows, games are not games, but
are deadly earnest. In the case of the present book, whose
impact depends to a large extent on correct spelling of the
+
I198
+
words, this means that it must not contain any printing or
other errors. And although the authors were naturally well
aware of this, some errors have nevertheless escaped their
notice: Konrad Lorenz (in the list of Nobel prizewinners in
Appendix F) is not a Dutchman, it was Unverdorben who
isolated aniline by distillation of indigo (not Herr Underderben, as given in Appendix A), in V6gtle the umlaut has
been put over the wrong letter, and so on. These are mere
trifles, but the absence of an index of names must be either
the final joke of the book, or a bad joke.
From time to time a plea is made for making the chemical literature more “human”-it is said to be too dry and
sterile, so that one can no longer recognize the real author
behind the words. It cannot be said too strongly that any
such move is to be avoided. In our writing most of us are
far from being great stylists, let alone literary giants, and
most of our work would not gain in value by having a “humanizing” introduction included. But if now and again
other books as entertaining as the all too human “Name
Game” were to appear, from which one could similarly
learn a surprising amount about new developments in
chemistry-that would really be fine.
Henning Hopf [NB 907 IE]
Institut fur Organische Chemie
der Technischen Universitat Braunschweig (FRG)
The Surface Scientist’s Guide to Organometallic Chemistry.
By M . R . Albert and J. T. Yates, Jr. American Chemical
Society, Washington, D C (USA) 1987. xiii, 214 pp.,
bound, $ 59.95 ($49.95 in USA and Canada).-ISBN 084 12-1003-9
Since the pioneering work of Earl Muetterties, organometallic chemistry has received increasing attention by surface chemists and surface physicists. It is therefore not surprising that the authors of this little book have dedicated it
to the memory of Muetterties. He showed convincingly
that the structures and chemical properties of chemisorption systems can be discussed in terms of the analogous
interactions between transition metal centers and their ligands.
The book by Albert and Yates clearly emphasizes the importance of organometallic chemistry for the chemistry
and physics of surfaces, and addresses mainly surface
chemists and surface physicists. An introduction (Chapter
l), is followed in Chapter 2 (Basic Coordination Chemistry) by a concise qualitative summary of theories of chemical bonding in coordination compounds. Chapter 3 (Overview of Coordination Ligands) is the longest chapter of the
book, and occupies a central position. It begins with a description of the main methods available for preparing surface complexes and ligands on well-characterized metallic
surfaces in ultra-high vacuum. This is followed by a detailed discussion of the bonding situations and reactivities
for 13 different classes of Iigands: lone-pair donors, diatomic ligands, substituted diatomic ligands, systems with
cumulenes, heteroolefins, triatomic pseudohalogens, organic chelates, nonmetal oxyanions, aromatics, heterocycles, electron deficient ligands, molecular fragments and,
lastly, atomic species. The discussion points out qualitative
analogies between molecular compounds and chemisorption systems, with regard to their geometric and electronic
structures and their reactivity (with particular reference to
catalytic reactions). In cases where there are no comparative data for ligands and surfaces, the authors draw attention to these gaps in knowledge, as potential research topAnyen, Chem Inf.Ed Engl 27/1988)
No 9
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