The Calculation of Molecular Volumes and the Use of Volume Analysis in the Investigation of Structured Media and of Solid-State Organic Reactivity

Journal of the American Chemical Society

Volumn 105, Issue 16, 1983, Pages 5220-5225

  Gavezzotti, A ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PHYSICAL CHEMISTRY;

EID: 0020799931     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00354a007     Document Type: Article

References (32)

1. See for a general view: Richards, W.G.; Walker, T.E.H.; Farnell, L.; Scott, P.R. “Bibliography of ab initio Molecular Wave Functions: Supplement for 1970-1973”; Clarendon Press: Oxford, 1974.
2. In such terms, defining molecular shape and size is equivalent to choosing a threshold value for the charge density to define molecular boundaries; see, for example: Bader, R.F.W.; Henneker, W.H.; Cade, P.E.J. Chem. Phys. 1967, 46, 3341.
3. Kennard, O.; Watson, D.G.; Allen, F.H.; Weeds, S.M., Eds. “Molecular Structures and Dimensions”; International Union of Crystallography, Polycrystal Book Service: Pittsburgh, 1979; Vol. 1-10.
4. Kitaigorodski, A.I. “Organic Chemical Crystallography”; Consultants Bureau: New York, 1961.
5. Kitaigorodski, A.I. “Molecular Crystals and Molecules”; Academic Press: New York, 1973.
6. Gavezzotti, A. Nouv. J. Chim. 1982, 6, 443.
7. See, for instance, Coppens, P.; Stevens, E.D. In “Advances in Quantum Chemistry”; Lowdin, P.-O., Ed.; Academic Press: New York, 1977; Vol. 10, P 1.
8. Such terms are broadly defined as electrostatic; see for a recent example: Berkovitch-Yellin, Z.; Leiserowitz, L.J. Am. Chem. Soc. 1982, 104, 4052.
9. See, however: O'Shea, S.F.; Santry, D.P. Theor. Chim. Acta 1975, 37, 1.
10. Bondi, A. J. Phys. Chem. 1964, 68, 441.
11. Gavezzotti, A.; Simonetta, M. Chem. Rev. 1982, 82, 1.
12. We have used a compendium of data from: Sutton, L.E., Ed. “Tables of Interatomic Distances and Configurations in Molecules and Ions”; The Chemical Society: London, 1965; Pople, J.A.; Gordon, M.J. Am. Chem. Soc. 1967, 89, 4253, Table I.
13. For biphenyl and cyclohexane, the structural data from the X-ray analyses of Charbonneau and Kahn (Charbonneau, G.P.; Delugeard, Y. Acta Crystallogr., Sect. B 1976, B32, 1420.
14. Kahn, R.; Fourme, R.; André, D.; Renaud, M. Acta Crystallogr., Sect. B 1973, B29, 131) respectively, have been used in the calculation of molecular volume.
15. Mirsky, K. In “Computing in Crystallography, Proceedings of an International Summer School on Crystallographic Computing”; Delft University Press: Twente, 1978; p. 169.
16. Beringhelli, T.; Filippini, G.; Gavezzotti, A.; Simonetta, M. J. Mol. Struct., in press.
17. After completion of this work, we became aware that a method of molecular volume calculation similar to ours is mentioned in Meresse, A. Doctoral Thesis, Universitè de Bordeaux I, 1981, p. 185.
18. For the cryptand, See: Metz, B.; Moras, D.; Weiss, R. J. Chem. Soc., Perkin Trans. 2 1976, 423. We thank Dr. G. Wypff, Université de Strasbourg, for bringing these compounds to our attention.
19. For the crystal structures and structural data of the complexes, see: Moras, D.; Weiss, R. Acta Crystallogr., Sect. B 1973, B29, 396 and references therein.
20. Colombo, A.; Allegra, G. Atti Accad. Naz. Lincei 1967, 13, 41.
21. Allegra, G.; Farina, M.; Immirzi, A.; Colombo, A.; Rossi, U.; Broggi, R.; Natta, G.J. Chem. Soc. B 1967, 1020.
22. Allegra, G.; Farina, M.; Colombo, A.; Casagrande-Tettamanti, G.; Rossi, U.; Natta, G.J. Chem. Soc. B 1967, 1028.
23. See, for a review: Farina, M. Makromol. Chem., Suppl. 1981, 4, 21.
24. Colombo, A.; Allegra, G. Macromolecules 1971, 4, 579.
25. Filippini, G.; Gavezzotti, A.; Simonetta, M.; Mason, R. Nouv. J. Chim. 1981, 5, 211.
26. See ref 10 and references therein. The volume analysis method was presented in preliminary form at the VI International Conference on the Chemistry of the Organic Solid State, Freiburg, 1982; See: Gavezzotti, A. Mol. Cryst. Liq. Cryst. in press.
27. Jaffe, A.B.; Malament, D.S.; Slisz, E.P.; McBride, J.M. J. Am. Chem. Soc. 1972, 94, 8515 and references therein. Our calculations were based on the PI modification of AIBN.
28. Karch, N.J.; Koh, E.T.; Whitsel, B.L.; McBride, J.M. J. Am. Chem. Soc. 1975, 97, 6729.
29. McBride, J.M.; Merrill, R.A.J. Am. Chem. Soc. 1980, 102, 1723. McBride, J.M., personal communication.
30. Dwarakanath, K.; Prasad, P.N. J. Am. Chem. Soc. 1980, 102, 4254.
31. Gavezzotti, A.; Simonetta, M. Nouv. J. Chim. 1977, 2, 69.
32. Sukenik, C.N.; Bonapace, J.A.P.; Mandel, N.S.; Lau, P.; Wood, G.; Bergman, R.G. J. Am. Chem. Soc. 1977, 99, 851.