An ab initio MO study on the hydrolysis of methyl chloride

Journal of Molecular Structure: THEOCHEM

Volumn 461-462, Issue , 1999, Pages 417-427

  Aida, Misako ^a,c   Yamataka, Hiroshi ^b  

^a NATIONAL CANCER CENTER RESEARCH INSTITUTE   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Ab initio MO; Kinetic isotope effect; Methyl chloride hydrolysis; S(N)2 reaction; Solvation effect

Indexed keywords

METHYL CHLORIDE;

ARTICLE; COMPLEX FORMATION; HYDROGEN BOND; HYDROLYSIS; MOLECULAR MODEL; PROTON TRANSPORT;

EID: 0033515409     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(98)00453-9     Document Type: Article

References (33)

1. J.M. Harris, S.P. McManus (Eds.), Nucleophilicity, American Chemical Society, Washington, DC, 1987.
2. Morokuma K. J. Am. Chem. Soc. 104:1982;3732.
3. Ohta K., Morokuma K. J. Phys. Chem. 89:1985;5845.
4. Hu W.-P., Truhlar D.G. J. Am. Chem. Soc. 116:1994;7797.
5. Okuno Y. J. Chem. Phys. 105:1996;5817.
6. Gonzales-Lafont A., Truong T.N., Truhlar D.G. J. Phys. Chem. 95:1991;4618.
7. Tucker S.C., Truhlar D.G. J. Am. Chem. Soc. 112:1990;3347.
8. Zhao X.G., Tucker S.C., Truhlar D.G. J. Am. Chem. Soc. 113:1991;826.
9. Hwang J.-K., King G., Creighton S., Warshel A. J. Am. Chem. Soc. 110:1988;5297.
10. O. Tapia, J. Bertran (Eds.), Solvent Effects and Chemical Reactivity, Kluwer Academic Publishers, Dordrecht, 1996.
11. Yamataka H., Aida M. Chem. Phys. Lett. 289:1998;5.
12. M. Dupuis, A. Marquez, E.R. Davidson, HONDO 96, available from the Quantum chemistry Program Exchange, Indiana University.
13. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T.A. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andress, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, GAUSSIAN 94, Revision C.2, Gaussian Inc., Pittsburgh, PA, 1995.
14. Møller C., Plesset M.S. Phys. Rev. 46:1934;618.
15. Fukui K. J. Phys. Chem. 74:1970;4161.
16. Ishida K., Morokuma K., Komornicki A. J. Chem. Phys. 66:1977;2153.
17. Wong M.W., Frisch M.J., Wiberg K.B. J. Am. Chem. Soc. 113:1991;4776.
18. Pople J.A., Scott A.P., Wong M.W., Radom L. Israel J. Chem. 33:1993;345.
19. W.A. Van Hook, in: C.J. Collins, N.S. Bowman (Eds.), Isotope Effects in Chemical Reactions, Van Nostrand-Reinhold, New York, 1970, Chapter 1.
20. Re S., Osamura Y., Suzuki Y., Schaefer III H.F. J. Chem. Phys. 109:1998;973.
21. Palinkas G., Riede W.O., Heinzinger K. Z. Naturforsch. 32A:1977;1137.
22. Lias S.G., Bartmess J.E., Holmes J.L., Levin R.D., Mallard G.W. J. Phys. Chem. Ref. Data Supple. 17:1988;1.
23. Abraham M.H., McLennan D.J. J. Chem. Soc. Perkin. 2:1977;873.
24. Llewellyn J.A., Robertson R.E., Scott J.M.W. Can. J. Chem. 38:1960;222.
25. Bender M.L., Hoeg D.F. J. Am. Chem. Soc. 79:1957;5649.
26. A. Fry, in: C.J. Collins, N.S. Bowman (Eds.), Isotope Effects in Chemical Reactions, Van Nostrand-Reinhold, New York, 1970, Chapter 6.
27. Laughton P.M., Robertson R.E. Can. J. Chem. 34:1956;1714.
28. Swain C.G., Cardinaud R., Ketley A.D. J. Am. Chem. Soc. 77:1955;934.
29. Swain C.G., Thornton E.R. J. Am. Chem. Soc. 84:1962;822.
30. Olivier S.C.J. Rec. Trav. Chim. 56:1937;247.
31. L. Melander, W.H. Saunders Jr., Reaction Rates of Isotopic Molecules, Wiley, New York, 1979.
32. L.B. Sims, D.E. Lewis, in: E. Buncel, C.C. Lee (Eds.), Isotopes in Organic Chemistry, vol. VI, Elsevier, Amsterdam, 1984, Chapter 4.
33. Yamataka H., Ando T. J. Phys. Chem. 85:1981;2281.