Microhydration effects on a model SN 2 reaction in a nonpolar solvent

Journal of Chemical Physics

Volumn 130, Issue 19, 2009, Pages

  Nelson, Katherine V ^a   Benjamin, Ilan ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BARRIER HEIGHTS; BULK WATER; CL REACTION; ENERGY PROFILE; HIGHLY SENSITIVE; MICRO-HYDRATION; NON-POLAR SOLVENTS; NUCLEOPHILIC SUBSTITUTION REACTIONS; RATE OF CHANGE; REACTION COORDINATES; REACTIVE SYSTEM; SOLVENT STABILIZATION; TRANSITION STATE; TRANSITION STATE THEORIES; VALENCE BOND MODELS; WATER MOLECULE;

ACTIVATION ENERGY; CHLORINE COMPOUNDS; ELECTRONIC STRUCTURE; FREE ENERGY; RATE CONSTANTS; SUBSTITUTION REACTIONS;

MOLECULES;

EID: 65949122069     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.3138902     Document Type: Article

References (57)

1. C. K. Ingold, Structure and Mechanism in Organic Chemistry, 2nd ed. (Cornell University, Ithaca, NY, 1969).
2. A. Warshel and R. M. Weiss, J. Am. Chem. Soc. 0002-7863 102, 6218 (1980). 10.1021/ja00540a008
3. J. K. Hwang, G. King, S. Creighton, and A. Warshel, J. Am. Chem. Soc. 0002-7863 110, 5297 (1988). 10.1021/ja00224a011
4. J. Chandrasekhar, S. F. Smith, and W. L. Jorgensen, J. Am. Chem. Soc. 0002-7863 106, 3049 (1984). 10.1021/ja00322a059
5. W. L. Jorgensen and J. K. Buckner, J. Phys. Chem. 0022-3654 90, 4651 (1986). 10.1021/j100410a037
6. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed. (Springer-Verlag, Weinheim, 1988).
7. J. R. Mathis, R. Bianco, and J. T. Hynes, J. Mol. Liq. 0167-7322 61, 81 (1994). 10.1016/0167-7322(94)00754-3
8. J. Villa, J. Bentzien, A. Gonzalez-Lafont, J. M. Lluch, J. Bertran, and A. Warshel, J. Comput. Chem. 0192-8651 21, 607 (2000). 10.1002/(SICI)1096- 987X(200006)21:8<607::AID-JCC3>3.0.CO;2-R
9. X. G. Zhao, D. H. Lu, Y. P. Liu, G. C. Lynch, and D. G. Truhlar, J. Chem. Phys. 0021-9606 97, 6369 (1992). 10.1063/1.463698
10. Y. Okuno, J. Chem. Phys. 0021-9606 105, 5817 (1996). 10.1063/1.472424
11. M. Re and D. Laria, J. Chem. Phys. 0021-9606 105, 4584 (1996). 10.1063/1.472539
12. A. A. Mohamed and F. Jensen, J. Phys. Chem. A 1089-5639 105, 3259 (2001). 10.1021/jp002802m
13. P. B. Balbuena, K. P. Johnston, and P. J. Rossky, J. Am. Chem. Soc. 0002-7863 116, 2689 (1994). 10.1021/ja00085a087
14. P. B. Balbuena, K. P. Johnston, and P. J. Rossky, J. Phys. Chem. 0022-3654 99, 1554 (1995). 10.1021/j100005a029
15. G. E. Bennett, P. J. Rossky, and K. P. Johnston, J. Phys. Chem. 0022-3654 99, 16136 (1995). 10.1021/j100043a065
16. L. W. Flanagin, P. B. Balbuena, K. P. Johnston, and P. J. Rossky, J. Phys. Chem. 0022-3654 99, 5196 (1995). 10.1021/j100014a047
17. C. S. Pomelli and J. Tomasi, J. Phys. Chem. A 1089-5639 101, 3561 (1997). 10.1021/jp962358g
18. M. H. M. Olsson and A. Warshel, J. Am. Chem. Soc. 0002-7863 126, 15167 (2004). 10.1021/ja047151c
19. J. E. Klijn and J. B. F. N. Engberts, Langmuir 0743-7463 21, 9809 (2005). 10.1021/la0504715
20. D. Landini, A. Maia, and A. Rampoldi, J. Org. Chem. 0022-3263 54, 328 (1989). 10.1021/jo00263a013
21. A. Maia, Pure Appl. Chem. 0033-4545 67, 697 (1995). 10.1351/ pac199567050697
22. D. Albanese, D. Landini, A. Maia, and M. Penso, Ind. Eng. Chem. Res. 0888-5885 40, 2396 (2001). 10.1021/ie0008124
23. C. M. Starks, C. L. Liotta, and M. Halpern, Phase Transfer Catalysis (Chapman and Hall, New York, 1994).
24. Y. H. Shao, M. V. Mirkin, and J. F. Rusling, J. Phys. Chem. B 1089-5647 101, 3202 (1997). 10.1021/jp9702309
25. M. Makosza, Pure Appl. Chem. 0033-4545 72, 1399 (2000). 10.1351/pac200072071399
26. D. Albanese, Catal. Rev.-Sci. Eng. 0161-4940 45, 369 (2003). 10.1081/CR-120025538
27. Interfacial Catalysis, edited by, A. G. Volkov, (Dekker, New York, 2003).
28. C. A. Eckert, C. L. Liotta, D. Bush, J. S. Brown, and J. P. Hallett, J. Phys. Chem. B 1089-5647 108, 18108 (2004). 10.1021/jp0487612
29. D. K. Bohme and A. B. Raksit, Can. J. Chem. 0008-4042 63, 3007 (1985). 10.1139/v85-499
30. X. G. Zhao, S. C. Tucker, and D. G. Truhlar, J. Am. Chem. Soc. 0002-7863 113, 826 (1991). 10.1021/ja00003a015
31. J. M. Hayes and S. M. Bachrach, J. Phys. Chem. A 1089-5639 107, 7952 (2003). 10.1021/jp035407f
32. J. R. Pliego, J. Phys. Chem. B 1089-5647 113, 505 (2009). 10.1021/jp808581t
33. I. Benjamin, J. Chem. Phys. 0021-9606 129, 074508 (2008). 10.1063/1.2970083
34. J. P. Bergsma, B. J. Gertner, K. R. Wilson, and J. T. Hynes, J. Chem. Phys. 0021-9606 86, 1356 (1987). 10.1063/1.452224
35. S. E. Huston, P. J. Rossky, and D. A. Zichi, J. Am. Chem. Soc. 0002-7863 111, 5680 (1989). 10.1021/ja00197a027
36. J. L. Gao, J. Am. Chem. Soc. 0002-7863 113, 7796 (1991). 10.1021/ja00020a070
37. Y. J. Cho, S. R. Vandelinde, L. Zhu, and W. L. Hase, J. Chem. Phys. 0021-9606 96, 8275 (1992). 10.1063/1.462331
38. R. Bianco, S. Miertus, M. Persico, and J. Tomasi, Chem. Phys. 0301-0104 168, 281 (1992). 10.1016/0301-0104(92)87162-3
39. M. Aguilar, R. Bianco, S. Miertus, M. Persico, and J. Tomasi, Chem. Phys. 0301-0104 174, 397 (1993). 10.1016/0301-0104(93)80006-U
40. M. Sato, H. Yamataka, Y. Komeiji, Y. Mochizuki, T. Ishikawa, and T. Nakano, J. Am. Chem. Soc. 0002-7863 130, 2396 (2008). 10.1021/ja710038c
41. S. C. Tucker and D. G. Truhlar, J. Am. Chem. Soc. 0002-7863 112, 3338 (1990). 10.1021/ja00165a013
42. J. -P. Hansen and I. R. McDonald, Theory of Simple Liquids, 2nd ed. (Academic, London, 1986).
43. A. L. McClellan, Tables of Experimental Dipole Moments (Freeman, San Francisco, 1963).
44. I. Benjamin, J. Chem. Phys. 0021-9606 103, 2459 (1995). 10.1063/1.470695
45. T. M. Chang and L. X. Dang, J. Phys. Chem. B 1089-5647 101, 10518 (1997). 10.1021/jp972101y
46. T. M. Chang, L. X. Dang, and K. A. Peterson, J. Phys. Chem. B 1089-5647 101, 3413 (1997). 10.1021/jp9638550
47. J. I. Timoneda and J. T. Hynes, J. Phys. Chem. 0022-3654 95, 10431 (1991). 10.1021/j100178a034
48. R. S. Mulliken, C. A. Rieke, D. Orloff, and H. Orloff, J. Chem. Phys. 0021-9606 17, 1248 (1949). 10.1063/1.1747150
49. D. Chandler, Introduction to Modern Statistical Mechanics (Oxford University Press, Oxford, 1987).
50. G. King and A. Warshel, J. Chem. Phys. 0021-9606 93, 8682 (1990). 10.1063/1.459255
51. B. J. Berne, M. Borkovec, and J. E. Straub, J. Phys. Chem. 0022-3654 92, 3711 (1988). 10.1021/j100324a007
52. B. J. Gertner, K. R. Wilson, and J. T. Hynes, J. Chem. Phys. 0021-9606 90, 3537 (1989). 10.1063/1.455864
53. R. M. Whitnell and K. R. Wilson, in Reviews in Computational Chemistry, edited by, K. B. Lipkowitz, and, D. B. Boyd, (VCH, New York, 1993).
54. M. P. Allen and D. J. Tildesley, Computer Simulation of Liquids (Clarendon, Oxford, 1987).
55. B. J. Gertner, J. P. Bergsma, K. R. Wilson, S. Lee, and J. T. Hynes, J. Chem. Phys. 0021-9606 86, 1377 (1987). 10.1063/1.452225
56. J. T. Hynes, in The Theory of Chemical Reactions, edited by, M. Baer, (CRC, Boca Raton, FL, 1985), Vol. 4, p. 171.
57. J. P. Bergsma, B. J. Gertner, K. R. Wilson, and J. T. Hynes, J. Chem. Phys. 0021-9606 86, 1356 (1987). 10.1063/1.452224