Distinction between the weak hydrogen bond and the van der Waals interaction

Abstract

The angular distributions of C–H···O interactions for different types of C–H groups show that the directionality decreases with decreasing C–H polarisation, but that it is still clearly recognisable for methyl groups; for C–H···H–C van der Waals contacts, in contrast, isotropic angular characteristics are observed.

References

1. G. R. Desiraju, Acc. Chem. Res., 1991, 24, 290; 1996, 29, 441.
2. T. Steiner, Chem. Commun., 1997, 727.
3. A. Allerhand, P. von and P. Schleyer, J. Am. Chem. Soc., 1963, 85, 1715.
4. D. J. Sutor, Nature, 1962, 195, 68; J. Chem. Soc., 1963, 1105.
5. V. R. Pedireddi and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1992, 988 and references cited therein.
6. T. Steiner, J. Chem. Soc., Chem. Commun., 1994, 2341.
7. J. J. Novoa, B. Tarron, M.-H. Whangbo and J. M. Williams, J. Chem. Phys., 1991, 95, 5179; X. Yan, S. Wang, M. Hodoscek and G. W. A. Milne, J. Mol. Struct.: THEOCHEM, 1994, 309, 279; T. van Mourik and F. B. van Duijneveldt, J. Mol. Struct.: THEOCHEM, 1995, 341, 63.
8. J. Donohue, in Structural Chemistry and Molecular Biology, ed. A. Rich and N. Davidson, Freeman, San Francisco, 1968, p. 443.
9. F. A. Cotton, L. M. Daniels, G. T. Jordan IV and C. A. Murillo, Chem. Commun., 1997, 1673.
10. G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures, Springer, Berlin, 1991.
11. F. H. Allen and O. Kennard, Chem. Des. Autom. News, 1993, 8, 1.
12. A. Bondi, J. Phys. Chem., 1964, 68, 441.
13. J. Kroon and J. A. Kanters, Nature, 1974, 248, 667.
14. P. Seiler, L. Isaacs and F. Diederich, Helv. Chim. Acta, 1996, 79, 1047.
15. N. N. L. Madhavi, A. K. Katz, H. L. Carrell, A. Nangia and G. R. Desiraju, Chem. Commun., 1997, 1953.