Supramolecular motifs: Concerted multiple phenyl embraces between Ph 4P+ cations are attractive and ubiquitous

Chemistry - A European Journal

Volumn 2, Issue 5, 1996, Pages 481-486

  Dance, Ian ^a   Scudder, Marcia ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Cations; Crystal structures; Phenyl rings; Supramolecular chemistry; Tetraphenylphosphonium ions

Indexed keywords

CAMBRIDGE STRUCTURAL DATABASES; CENTROSYMMETRY; NONBONDED INTERACTION; PHENYL RINGS; SUPRAMOLECULAR MOTIFS; VAN DER WAALS;

CRYSTAL STRUCTURE; SUPRAMOLECULAR CHEMISTRY; VAN DER WAALS FORCES;

POSITIVE IONS;

EID: 0039218720     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020505     Document Type: Article

References (43)

1. a) J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1988, 27, 89-112;
2. b) J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1990, 29, 1304-1319.
3. A. J. Pertsin, A. I. Kitaigorodskii, The Atom-Atom Potential Method, Springer, Berlin, 1987.
4. F. H. Allen, J. E. Davies, J. J. Galloy, O. Johnson, O. Kennard, C. F. Macrae, E. M. Mitchell, G. F. Mitchell, J. M. Smith, D. G. Watson, J. Chem. Inf. Comput. Sci. 1991, 31, 187-204.
5. H.-B. Burgi, J. D. Dunitz, Structure Correlation, VCH, Weinheim, 1994.
6. I. Dance, M. L. Scudder, J. Chem. Soc. Chem. Commun. 1995, 1039-1040.
7. I. Dance in Perspectives in Supramolecular Chemistry (Ed.: G. Desiraju), Wiley, 1996, ch. 5, pp. 137-233.
8. A. I. Kitaigorodskii, Molecular Crystals and Molecules, Academic Press, New York, 1973.
9. G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, Amsterdam, 1989.
10. a) S. K. Burley, G. A. Petsko, Science 1985, 229, 23;
11. b) S. K. Burley, G. A. Petsko, J. Am. Chem. Soc. 1986, 108, 7995-8001.
12. a) A. Gavezzotti, G. R. Desiraju, Acta Crystallogr. 1988, B44, 427-434;
13. b) G. R. Desiraju, A. Gavezzotti, ibid. 1989, B45, 473-482;
14. c) A. Gavezzotti, Chem. Phys. Lett. 1989, 161, 67;
15. d) A. Gavezzotti, Acta Crystallogr. 1990, B46, 275-283.
16. R. O. Gould, A. M. Gray, P. Taylor, M. D. Walkinshaw, J. Am. Chem. Soc. 1985, 107, 5921-5927.
17. a) J. Singh, J. M. Thornton, J. Mol. Biol. 1990, 211, 595-615;
18. b) C. A. Hunter, J. Singh, J. M. Thornton, J. Mol. Biol. 1991, 218, 837-846
19. a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534;
20. b) C. A. Hunter, Philos. Trans. R. Soc. London 1993, A345, 77-85;
21. c) C. A. Hunter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1584-1586.
22. a) D. Braga, F. Grepioni, Organometallics 1991, 10, 2563-2569;
23. b) D. Braga, P. J. Dyson, F. Grepioni, B. F. G. Johnson, Chem. Rev. 1994, 94, 1585-1620.
24. G. Klebe, F. Diederich, Philos. Trans. R. Soc. London 1993, A34S, 37-48.
25. D. E. Williams, Acta Crystallogr. 1980, A36, 715-723.
26. G. Karlström, P. Linse, A. Wallqvist, B. Jönsson, J. Am. Chem. Soc. 1983, 105, 3777-3782.
27. S. L. Price, A. J. Stone, J. Chem. Phys. 1987, 86, 2859-2868.
28. J.-H. Lii, N. L. Allinger, J. Am. Chem. Soc. 1989, 111, 8576-81.
29. W. L. Jorgensen, D. L. Severance, J. Am. Chem. Soc. 1990, 112, 4768-4774.
30. P. Hobza, H. L. Selzle, E. W. Schlag, J. Am. Chem. Soc. 1994, 116, 3500-3506.
31. K. C. Janda, J. C. Hemminger, J. S. Winn, S. E. Novick, S. J. Harris, W. Klemperer, J. Chem. Phys. 1975, 63, 1419.
32. J. M. Steed, T. A. Dixon, W. Klemperer, J. Chem. Phys. 1979, 70, 4940.
33. J. R. Grover, E. A. Walters, E. T. Hui, J. Phys. Chem. 1987, 91, 3233-7.
34. + to necessitate separate analysis of the concerted phenyl embraces.
35. Atom partial charges which have been used for benzene are +0.153 (H), -0.153 (C) [16] or +0.115 (H), -0.115 (C) [20]: the coulombic components of the intermolecular energy are relatively insensitive to the magnitudes of the charges in this range.
36. 2 for dimers, oligomers, and bulk benzene [13,16,20,21,24]. The calculations in this paper probably yield a small overestimate of the phenyl-phenyl intermolecular energies.
37. Program Discover, Biosym/MSI, San Diego (USA).
38. The terms acceptor and donor, and the arrows in figures, are conveniently used here in the same sense as hydrogen bonding, but the interaction is largely nonvectorial coulombic.
39. I. G. Dance, M. L. Scudder, unpublished results.
40. a) D. M. P. Mingos, A. L. Rohl, J. Chem. Soc. Dalton Trans. 1991, 3419;
41. b) D. M. P. Mingos, A. L. Rohl, J. Burgess, ibid. 1993, 423-426.
42. a) J. D. Dunitz, H.-B. Burgi, in ref. [4], ch. 2;
43. b) W. B. Schweizer, in ref. [4], ch. 9.