Quantum chemical study of the thermodynamic and kinetic aspects of the SN2 reaction in gas phase and solution using a DFT interpretation

Journal of Physical Chemistry A

Volumn 105, Issue 3, 2001, Pages 591-601

  Safi, B ^a   Choho, K ^a   Geerlings, P ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CONTINUUM MECHANICS; CORRELATION METHODS; POLARIZATION; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; SULFUR COMPOUNDS; THERMODYNAMICS;

NUCLEOPHILES;

REACTION KINETICS;

EID: 0035131368     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp000977q     Document Type: Article

References (69)

1. Parr, R. G.; Wang, W. Density functional theory of atoms and molecules; Oxford University Press: Oxford, UK, 1989.
2. Fukui, K.; Yonezawa, T.; Shingu, H. J. Chem. Phys. 1972, 20, 722.
3. (a) Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533.
4. (b) Pearson, R. G.; Songstad, J. J. Am. Chem. Soc. 1967, 89, 1827.
5. Huheey, J. E. Inorganic Chemistry, 3rd ed.; Harper & Row Publishers: New York, 1983; p 312.
6. Parr, R. G.; Chattaraj, P. K. J. Am. Chem. Soc. 1991, 113, 1854.
7. Pearson, R. G. Acc. Chem. Res. 1993, 26, 250.
8. De Proft, F.; Langenaeker, W.; Geerlings, P. J. Phys. Chem. 1993, 97, 1821.
9. Langenaeker, W.; Coussement, N.; De Proft, F.; Geerlings, P. J. Phys. Chem. 1994, 98, 3010.
10. De Proft, F.; Amira, S.; Choho, K.; Geerlings, P. J. Phys. Chem. 1994, 98, 5227.
11. De Proft, F.; Langenaeker, W.; Geerlings, P. Int. J. Quantum. Chem. 1995, 55, 459.
12. Choho, K.; Langenaeker, W.; Van De Woude, G.; Geerlings, P. J. Mol. Struct. (THEOCHEM) 1995, 338, 293.
13. Choho, K.; Langenaeker, W.; Van De Woude, G.; Geerlings, P. J. Mol. Struct. (THEOCHEM) 1996, 362, 305.
14. Damoun, S.; Van De Woude, G.; Mendez, F.; Geerlings, P. J. Phys. Chem. 1997, A101, 886.
15. Damoun, S.; Van De Woude, G.; Choho, K.; Geerlings, P. J. Phys. Chem. 1999, A103, 7861.
16. Roy, R. K.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Org. Chem. 1999, 12, 503.
17. De Proft, F.; Langenaeker, W.; Geerlings, P. J. Phys. Chem. 1993, 97, 1826.
18. Safi, B.; Choho, K.; De Proft, F.; Geerlings, P. J. Phys. Chem. 1998, A102, 5253.
19. Parker, A. J. Q. Rev. (London) 1962, 16, 163.
20. Menschutkin, N. Z. Phys. Chem. 1890, 6, 41.
21. Laidler, K. J.; King, M. C. J. Phys. Chem. 1983, 87, 2657.
22. Kreevoy, M. M.; Truhlar, D. G. Transition State Theory. In Investigation of Rates and Mechanisms of Reactions; Techniques of Chemistry Series, Vol. IV; Bernasconi, C. F., Ed.; Wiley: New York, 1986; Part I, p 13 ff.
23. Shaik, S. S.; Schlegel, H. B.; Wolfe, S. Theoretical Aspects of Physical Organic Chemistry; John Wiley: New York, 1992.
24. Shaik, S. S.; Hiberty, P. C. Adv. Quantum Chem. 1995, 26, 99.
25. Gazquez, J. L. J. Phys. Chem. 1997, A101, 8967.
26. Pross, A. Theoretical and physical principles of organic reactivity; Wiley: New York, 1995; Part C.
27. Su, T.; Wang, H.; Hase, W. L. J. Phys. Chem. 1998, A102, 9819.
28. Olsmtead, J. I. J. Am. Chem. Soc. 1977, 99, 4219.
29. Farneth, W. E.; Brauman, J. I. J. Am. Chem. Soc. 1976, 98, 7891.
30. Asubiojo, O. I.; Brauman, J. I. J. Am. Chem. Soc. 1979, 101, 3715.
31. Jasinski, J. M.; Brauman, J. I. J. Am. Chem. Soc. 1979, 101, 3715.
32. Pellerite, M. J.; Brauman, J. I. J. Am. Chem. Soc. 1980, 102, 5993.
33. Glasstone, S.; Laidler, K. J.; Eyring, H. The Theory of the Rate Processes; McGraw-Hill: New York, 1941.
34. Baer, T.; Hase, W. I. Unimolecular Reaction Dynamic-Theory and Experiments; New York, 1996.
35. Nguyen, L. T.; Le, T. N.; De Proft, F.; Chandra, A. K.; Langenaeker, W.; Nguyen, M. T. Geerlings, P. J. Am. Chem. Soc. 1999, 121, 5992.
36. Le, T. N.; Nguyen, L. T.; De Proft, F.; Chandra, A. K.; Geerlings, P.; Nguyen, M. T. Perkin Trans. 2 1999, 1249.
37. Hard and Soft Acids and Bases; Pearson, R. G., Ed.; Dowden, Hutchinson, and Ross, Inc.; Stroudsburg, PA, 1973.
38. Datta, D. Inorg. Chem. 1992, 31, 2797.
39. Pearson, R. G. Inorg. Chim. Acta 1992, 198, 781.
40. Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512.
41. Yang, W.; Lee, C.; Ghosh, S. K. J. Phys. Chem. 1985, 89, 6723.
42. Datta, D. J. Phys. Chem. 1992, 96, 2409.
43. Chattaraj, P. K.; Nath, S.; Sannigrahi, A. B. J. Phys. Chem. 1994, 98, 9143.
44. Ghanty, T. K.; Ghosh, S. K. J. Phys. Chem. 1996, 100, 12295.
45. Politzer, P.; Murray, J. S.; Grice, M. E. In Structure and Bonding 80: Chemical Hardness; Sen, K. D., Ed.; Springer-Verlag: Berlin, 1993; p 101.
46. Taft, R. W.; Topsom, R. D. Prog. Phys. Org. Chem. 1987, 16, 1.
47. Geerlings, P.; De Proft, F. Int. J. Quantum. Chem. 2000, 80, 227.
48. Tomasi, J.; Perisco, M. Chem. Rev. 1994, 94, 2027.
49. Miertus, S.; Scrocco, E.; Tomasi, J. J. Chem. Phys. 1981, 55, 117.
50. Wiberg, K. B.; Keith, T. A.; Frisch, M. J.; Murcko, M. J. Phys. Chem. 1995, 99, 9072.
51. Cohen, H. D.; Roothaan, C. C. J. J. Chem. Phys. 1965, 43, S34.
52. Parr, R. G.; Donnely, R. A.; Levy, M.; Palke, W. E. J. Chem. Phys. 1978, 68, 3801.
53. Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512.
54. Yang, W.; Parr, R. G. Proc. Natl Acad. Sci. U.S.A. 1985, 82, 6723.
55. Mulliken, R. S. J. Chem. Phys. 1934, 2, 782.
56. Koopmans, T. Physica 1934, 1, 104.
57. Bester, B. H.; Merz, K. M.; Kollman, P. A. J. Comput. Chem. 1990, 11, 431.
58. Singh, B. H.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129.
59. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.3; Gaussian Inc.: Pittsburgh, PA, 1995.
60. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 98, Revision A.I; Gaussian Inc.: Pittsburgh, PA, 1995.
61. Olmstead, W. N.; Brauman, J. I. J. Am. Chem. Soc. 1977, 99, 4219.
62. Hehre, W. J.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1972, 94, 1496.
63. Hehre, W. J.; Ditchfield, R.; Radom, L.; Pople, J. A. J. Am. Chem. Soc. 1974, 92, 4796.
64. Choho, K.; Van De Woude, G.; Van Lier, G.; Geerlings, P. J. Mol. Struct. (THEOCHEM) 1997, 417, 265.
65. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
66. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; 2nd ed.; Harper & Row Publishers: New York, 1981.
67. Cox, B. G.; Hedwig, G. R.; Parker, A. J.; Watts, D. W. Aust. J. Chem. 1974, 27, 477.
68. Ihrig, A. M.; Smith, S. L. J. Am. Chem. Soc. 1972, 94, 34.
69. Diercksen, G. H. F.; Karlson, M.; Tamm, T.; Zerner, M. C. Int. J. Quantum Chem. 1994, 28, 339.