What makes molecules beautiful? It may be their simplicity, a symmetrical structure. Or it may be their complexity, the richness of structural detail that is required for specific function. Sometimes the beauty of a molecule may be hidden, to be revealed only when its position in a sequence of transformations is made clear. Novelty, surprise, utility also playa role in molecular aesthetics, which is the subject of this contribution.
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References
1.
For a general introduction to molecules see the beautiful book byAtkinsP. W.: ‘Molecules’; 1987, New York, Scientific American Library.
2.
PaquetteL. A., TernanskyR. J., BaloghD. W. and KentgenG.: ‘Total synthesis of dodecahedrane’, J. Am. Chem. Soc., 1983, 105, 5446–5450.
3.
Dodecahedrane was recently synthesised in a very different way: FessnerW.-D., MurtyB. A. R. C., WörthJ., HunklerD, FritzH., PrinzbachH, RothW. D., Von Ragué SchleyerP., McewenA. B. and MeierW. F.: ‘Dodecahedrane aus [1.1.1.1] Pagodanen’, Ang. Chem., 1987, 99, 484–486.
4.
DoyleM., ParkerW., GunnP. A., MartinJ. and MacnicolD. D.: ‘Synthesis and conformational mobility of bicyclo(3, 3 ,3)undecane(manxane)’, Tetrahedron Lett., 1970, (42), 3619–3622.
5.
SekineY., BrownM. and BoekelheideV.: ‘[2.2.2.2.2.2](1,2,3,4,5,6) cyclophane: superphane’, J. Am. Chem. Soc., 1979, 101, 3126–3127.
6.
For an immensely enjoyable tour of the coined landscape of chemistry see NickonA. and SilversmithE. F.: ‘Organic chemistry: the name game’; 1987, Oxford, Pergamon. Structures1–3are drawn after this source.
7.
KöhlerJ. and SimonA.: ‘NaNb3O5F – eine Niob-Niob Dreifachbindung mit ‘side-on’-Koordination durch Nb-Atome’, Ang. Chem., 1986, 98, 1011–1012; S. J. Hibble, A. K. Cheetham and D. F. Cox: ‘Ca0sub75Nb3O6: a novel metal oxide containing niobium–niobium bonds. Characterization and structure refinement from synchrotron powder X-ray data’, Inorg. Chem., 1987, 26, 2389–2391.
8.
CalhordaM. J. and HoffmannR.: ‘Dimensionality and metal–metal and metal–oxygen bonding in the NaNb3O6 structure’, J. Am. Chem. Soc., 1988, 110, 8376–8385.
9.
KantI.: ‘Critique of judgment’, (trans. BernardJ. H.), 28; 1951, New York, Hafner.
10.
WassermanE.: ‘The preparation of interlocking rings: a catenane’, J. Am. Chem. Soc., 1960, 82, 4433–4434. For an elegant Möbius strip approach to catenanes see R. Wolovsky: ‘Interlocked ring systems obtained by the metathesis reaction of cyclodecene. Mass spectral evidence’, J. Am. Chem. Soc., 1970, 92, 2132–2133; D. A. Ben-Efraim, C. Batich and E. Wasserman: ‘Mass-spectral evidence for catenanes formed via a ‘Möbiusstrip’ approach’, J. Am. Chem. Soc., 1970, 92, 2133–2135. See also the ingenious work of J.-P. Sauvage and J. Weiss: ‘Synthesis of dicopper (I) [3] catenates: multiring interlocked coordinating systems’, J. Am. Chem. Soc., 1985, 107, 6108–6110.
11.
SchillG. and LüttringhausA.: ‘Gezielte Synthese von Catena-Verbindungen’, Ang. Chem., 1964, 76, 567–568.
12.
For some leading references on complexity in chemical synthesis, chemical similarity and chemical ‘distance’, see BertzS. H.: ‘Convergence, molecular complexity, and synthetic analysis’, J. Am. Chem. Soc., 1982, 104, 5801–5803; M. Wochner, J, Brandt, A. Von Scholley and I. Ugi: ‘Chemical similarity, chemical distance, and its exact determination’, Chimia, 1988, 42, 217–225; J. B. Hendrickson: ‘Systematic synthesis design. 6. Yield analysis and convergency’, J. Am. Chem. Soc., 1977, 99, 5439–5450.
13.
For an inspiring, original presentation of the achievements of organic synthesis see AnandN., BindraJ. S. and RanganathanS.: ‘Art, in organic synthesis’, 2ndedn;1988, New York, John Wiley and Sons.
14.
For leading references see GuyerP.: ‘Kant and the claims of taste’;1979, Cambridge, MA, Harvard University Press; D. W. Crawford: ‘Kant's aesthetic theory’; 1974, Madison, WI, University of Wisconsin Press.
15.
CrawfordD. W.: ‘Kant's aesthetic theory’, 49–51; 1974, Madison, WI, University of Wisconsin Press.
16.
CarrollN.: ‘Beauty and the genealogy of art theory’, Philos. Forum, to be published.
17.
For more information on haemoglobin seeDickersonR. E. and GeisI.: ‘Hemoglobin’;1983, Menlo Park, CA, Benjamin/Cummings; L. Stryer: ‘Biochemistry’, 3rd edn; 1988, San Francisco, CA, W. H. Freeman. I owe much to these books and to the original work of Max Perutz.
18.
JacobF.: ‘Evolution and tinkering’, Science, 1977, 196, 1161–1166.
19.
HoffmannR. and LaszloP.: ‘La représentation en chimie’, Diogène, 1989, 147, 24–54.
20.
ClarkD. N. and SchrockR. R.: ‘Multiple metal–carbon bonds, 12. Tungsten and molybdenum neopentylidyne and some tungsten neopentylidene complexes’, J. Am. Chem. Soc., 1978, 100, 6774–6776; M. R. Churchill and W. J. Youngs: ‘Crystal structure and molecular geometry of W(= CCMe3)(= CHCMe3)(CH2CMe3) (dmpe), a mononuclear tungsten (VI) complex with metal–alkylidyne, metal–alkylidene, and metal–alkyl linkages’, Inorg. Chem., 1979, 18, 2454–2458.
JohnsonB. F. G. and LewisJ.: ‘Transition-metal molecular clusters’, Adv. Inorg. Chem. Radiochem., 1981, 24, 225–355; J. S. Bradley: ‘The chemistry of carbido-carbonyl clusters’, Adv. Organomet. Chem., 1983, 22, 1–58.
23.
ScherbaumF., GrohmannA., HilberB., KrügerC. and SchmidbaurH.: “‘Aurophilie’ als Konsequenz relativistischer Effekte: das hexakis(triphenylphosanaurio) methan Dikation [(Ph3PAu)6C]2 +”, Ang. Chem., 1988, 100, 1602–1604.
24.
Some of these molecules were foreseen theoretically. See, for instance, Von Ragué SchleyerP., WürthweinE.-U., KaufmannE, ClarkT., and PopleJ. A.: ‘CLi5, CLi6, and the related effectively hypervalent first-row molecules, CLi5–nHn and CLi6–nHn’, J. Am. Chem. Soc., 1983, 105, 5930–5932; D. M. P. Mingos: ‘Molecular orbital calculations on cluster compounds of gold’, J. Chem. Soc. (Dalton Trans.), 1976, 1163–1169.
25.
BeardsleyM. C.: ‘Aesthetics’, 2nd edn; 1981, Indianapolis, IN, Hackett Publishing Co.; M. C. Beardsley:in‘The aesthetic point of view’, (ed. WreenM. J. and CallenD. M.); 1982, Ithaca, NY, Cornell University Press.
26.
GoodmanN.: ‘Languages of art’, 2nd edn; 1976, Indianapolis, IN, Hackett Publishing Co.
27.
AbramsM. H.: personal communication. See also G. Sircello: ‘A new theory of beauty’, 118–121; 1975, Princeton, NJ, Princeton University Press.
28.
I am grateful to Maria José Calhorda, Paul Houston, Barry Carpenter, Bruce Ganem, Noël Carroll, two reviewers and Donald W. Crawford for their comments and help in the preparation of this review, and to Sandra Ackerman for her editorial assistance. This article derives from four ‘marginalia’ that I wrote forAmerican Scientist1988, 76, 389–391, 604–605; 1989, 77, 177–178, 330–332). It has also been published in the Journal of Aesthetics and Art Criticism (1990, 48, (3), 191–204). I am grateful to the editors of this publication for permission to reprint the article here. The ink drawings were beautifully done, as always, by Elisabeth Fields and Jane Jorgensen. Max Perutz gave permission to reproduce one drawing of haemoglobin. One other was taken from the spectacular, illuminating graphics of haemoglobin designed by Irving Geis.
