Fivefold-Diamond Structure of Adamantane-1,3,5,7-tetracarboxylic Acid

Journal of the American Chemical Society

Volumn 110, Issue 12, 1988, Pages 3747-3754

  Ermer, Otto ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845280219     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00220a005     Document Type: Article

References (17)

1. For packing modes of carboxylic acids, see: Leiserowitz, L. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1976, B32, 775.
2. A somewhat comparable structure of interest in the present context has recently been derived for Cd(SC6H5)2: Craig, D.; Dance, I. G.; Garbutt, R. Angew. Chem., Int. Ed. Engl. 1986, 25, 165.
3. Instead of a slightly distorted (cubic) diamondlike structure (zinc-blende, sphalerite) of 1 a slightly distorted hexagonal diamondlike structure (wurtzite) would be a reasonable alternative. However, according to model building the interpenetration possibilities of several wurtzite-type lattices appear more restricted than of diamond-type lattices. A very readable monograph on diamond has recently appeared: Davies, G. Diamond; Adam Hilger: Bristol, U.K., 1984. For hexagonal diamond (lonsdaleite), see: (a) Frondel, C.; Marvin, U. B. Nature (London) 1967, 214, 587. Hanneman, R. E.; Strong, H. M.; Bundy, F. P. Science (Washington, D.C.) 1967, 155, 995.
4. Longley, W.; McIntosh, T. J. Nature (London) 1983, 303, 612. Thomas, E. L.; Alward, D. B.; Kinning, D. J.; Martin, D. C.; Handlin, D. L.; Fetters, L. J. Macromolecules 1986, 19, 2197. Note the interesting relationships with mathematical minimal surfaces discussed in these papers. It is noted further that the lattice type of the intermetallic Zintl phase NaTl corresponds to a mixed double-diamond structure with a diamond lattice formed by the thallium atoms and another symmetrically interpenetrating one (cf., Figure 3) of the same size made up of the sodium atoms. See: Lan-dolt-Börnstein Zahlenwerte und Funktionen aus Physik, Chemie, Astronomie, Geophysik und Technik; Springer: Berlin, West Germany, 1955; Vol. 1, Part 4, p 30. Other inorganic examples of double-diamondlike structures are provided by the silicate mineral neptunite, by Cu2O (cuprite), Zn(CN)2 and Cd(CN)2, and by three high-pressure modifications of ice: Cannillo, E.; Mazzi, F.; Rossi, G. Acta Crystallogr, 1966, 21, 200. Kamb, B.; Davis, B. L. Proc. Natl. Acad. Sci. U.S.A. 1964, 52, 1433. Kamb, B. Science (Washington D.C.) 1965, 150, 205. See also: Liebau, F. Structural Chemistry of Silicates; Springer: Berlin, West Germany, 1985; p 128.
5. Duchamp, D. J.; Marsh, R. E. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1969, B25, 5.
6. Stetter, H.; Bänder, O.-E.; Neumann, W. Chem. Ber. 1956, 89, 1922.
7. The tetragonal crystals of 1 are optically uniaxial positive: ncD(||c) = 1.6512 (5), n0D(⊥c) = 1.5909 (5); n̅D = (1.6512 + 1.5909 + 1.5909)/3 = 1.6110. These refractive indices were measured by O, Mcdenbach. Bochum, to whom we extend our appreciation, on a microrefractometer recently designed by himself: Medenbach O. Fortschr. Mineral 1985, 63, 111.
8. Ermer, O.; Bödecker, C.-D. Chem. Ber. 1981, 114, 652.
9. Ermer, O.; Dunitz, J. D.; Helv. Chim. Acta 1969, 52, 1861
10. Dieterich, D. A.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1974, 96, 6372.
11. Berkovitch-Yellin, Z.; Leiserowitz, L. J. Am. Chem. Soc. 1982, 104, 4052.
12. Lifson, S.; Hagler, A. T.; Dauber, P.; J. Am. Chem. Soc. 1979. 101, 5111.
13. Immirzi, A.; Perini, B. Acta Crystallogr., Sect. A: Cryst. Phys. Diffr. Theor. Gen. Crystallogr. 1977, A33, 216.
14. Ermer, O.; Eling, A. Angew. Chem., Int. Ed. Engl., in press.
15. For comparison with 5, the crystal structure of pentaerythritol, C-(CH2OH)4, appears to be of interest. This tetraalcohol also crystallizes tetragonally yet does not form diamondoid lattices. Presumably, this is at least partly due to the less suitable directionality of the hydrogen bonds of pentaerythritol as suggested by model considerations. Numerous crystallographic studies on pentaerythritol have been reported; see, e.g.: Eilerman, D.; Rudman, R. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1979, B35, 2458. Llewellyn, F. J.; Cox, E. G.; Goodwin, T. H. J. Chem. Soc. 1937, 883.
16. Herbstein, F. H.; Kapon, M.; Reisner, G. M. Proc. R. Soc. London, A 1981, 376, 301.
17. Farges, G.; Dreiding, A. S. Helv. Chim. Acta 1966, 49, 552. Rice, L. M.; Scott, K. R. J. Org. Chem. 1967, 32, 1966. Anteunis, M.; Geens, A.; van Cauwenberghe, R. Bull. Soc. Chim. Belg. 1973, 82, 573.