Effect of a phase transfer catalyst on the dynamics of an SN2 reaction. A molecular dynamics study

Journal of Physical Chemistry C

Volumn 115, Issue 5, 2011, Pages 2290-2296

  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; INTERFACE LOCATIONS; ION PAIRS; LIQUID/LIQUID INTERFACE; NUCLEOPHILIC ATTACK; ORGANIC PHASE; PHASE TRANSFER CATALYSTS; REACTION FREE ENERGY; TETRAMETHYLAMMONIUM; VALENCE BONDS; WATER MOLECULE;

CHLORINE COMPOUNDS; MOLECULAR DYNAMICS; NUCLEOPHILES; REACTION KINETICS;

CATALYSTS;

EID: 79952642814     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp110796n     Document Type: Article

References (63)

1. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase Transfer Catalysis; Chapman & Hall: New York, 1994.
2. Shao, Y. H.; Mirkin, M. V.; Rusling, J. F. J. Phys. Chem. B 1997, 101, 3202
3. Naik, S. D.; Doraiswamy, L. K. AIChE J. 1998, 44, 612
4. Makosza, M. Pure Appl. Chem. 2000, 72, 1399
5. Albanese, D. Catal. Rev. Sci. Eng. 2003, 45, 369
6. Interfacial Catalysis; Volkov, A. G., Ed.; Marcel Dekker: New York, 2003.
7. Eckert, C. A.; Liotta, C. L.; Bush, D.; Brown, J. S.; Hallett, J. P. J. Phys. Chem. B 2004, 108, 18108
8. Ingold, C. K. Structure and Mechanism in Organic Chemistry, 2 nd ed.; Cornell University: Ithaca, NY, 1969.
9. Warshel, A.; Weiss, R. M. J. Am. Chem. Soc. 1980, 102, 6218
10. Hwang, J. K.; King, G.; Creighton, S.; Warshel, A. J. Am. Chem. Soc. 1988, 110, 5297
11. Chandrasekhar, J.; Smith, S. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1984, 106, 3049
12. Jorgensen, W. L.; Buckner, J. K. J. Phys. Chem. 1986, 90, 4651
13. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2 nd ed.; Springer-Verlag: Weinheim, 1988.
14. Mathis, J. R.; Bianco, R.; Hynes, J. T. J. Mol. Liq. 1994, 61, 81
15. Hu, W.-P.; Truhlar, D. G. J. Am. Chem. Soc. 1994, 116, 7797
16. Vayner, G.; Houk, K. N.; Jorgensen, W. L.; Brauman, J. I. J. Am. Chem. Soc. 2004, 126, 9054
17. Almerindo, G. I.; Pliego, J. R. Chem. Phys. Lett. 2006, 423, 459
18. Pliego, J. R. J. Phys. Chem. B 2009, 113, 505
19. Kim, Y.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. A 2009, 113, 9109
20. Wang, H. F.; Borguet, E.; Eisenthal, K. B. J. Phys. Chem. B 1998, 102, 4927
21. Wang, H.; Borguet, E.; Eisenthal, K. B. J. Phys. Chem. 1997, 101, 713
22. Zhang, X.; Esenturk, O.; Walker, R. A. J. Am. Chem. Soc. 2001, 123, 10768
23. Steel, W. H.; Walker, R. A. Nature 2003, 424, 296
24. Zhang, X.; Steel, W. H.; Walker, R. A. J. Phys. Chem. B 2003, 107, 3829
25. Michael, D.; Benjamin, I. J. Chem. Phys. 1997, 107, 5684
26. Benjamin, I. J. Phys. Chem. A 1998, 102, 9500
27. Benjamin, I. Chem. Rev. 2006, 106, 1212
28. Landini, D.; Maia, A.; Rampoldi, A. J. Org. Chem. 1989, 54, 328
29. Maia, A. Pure Appl. Chem. 1995, 67, 697
30. Albanese, D.; Landini, D.; Maia, A.; Penso, M. Ind. Eng. Chem. Res. 2001, 40, 2396
31. Benjamin, I. J. Phys. Chem. B 2008, 112, 15801
32. Rose, D.; Benjamin, I. J. Phys. Chem. B 2009, 113, 9296
33. Bisson, P.; Xiao, H.; Kuo, M.; Kamelamela, N.; Shultz, M. J. J. Phys. Chem. A 2010, 114, 4051
34. Benjamin, I. J. Chem. Phys. 2008, 129, 074508
35. Nelson, K. V.; Benjamin, I. J. Chem. Phys. 2009, 130, 194502
36. Nelson, K. V.; Benjamin, I. J. Phys. Chem. C 2010, 114, 1154
37. Landini, D.; Maia, A. J. Mol. Catal. A: Chem. 2003, 204, 235
38. Gonzalez-Lafont, A.; Truhlar, D. G. In Chemical Reactions in Clusters; Bernstein, E. R., Ed.; Oxford University Press: Oxford, 1996; p 3.
39. Pomelli, C. S.; Tomasi, J. J. Phys. Chem. A 1997, 101, 3561
40. Mohamed, A. A.; Jensen, F. J. Phys. Chem. A 2001, 105, 3259
41. Olsson, M. H. M.; Warshel, A. J. Am. Chem. Soc. 2004, 126, 15167
42. Sato, M.; Yamataka, H.; Komeiji, Y.; Mochizuki, Y.; Ishikawa, T.; Nakano, T. J. Am. Chem. Soc. 2008, 130, 2396
43. Tucker, S. C.; Truhlar, D. G. J. Am. Chem. Soc. 1990, 112, 3338
44. Hansen, J.-P.; McDonald, I. R. Theory of Simple Liquids, 2 nd ed.; Academic: London, 1986.
45. McClellan, A. L. Tables of Experimental Dipole Moments; W. H. Freeman: San Francisco, 1963.
46. Benjamin, I. J. Chem. Phys. 1995, 103, 2459
47. Chang, T. M.; Dang, L. X. J. Phys. Chem. B 1997, 101, 10518
48. Tsun-Mei, C.; Dang, L. X.; Peterson, K. A. J. Phys. Chem. B 1997, 101, 3413
49. Hore, D. K.; Walker, D. S.; MacKinnon, L.; Richmond, G. L. J. Phys. Chem. C 2007, 111, 8832
50. Schweighofer, K. J.; Benjamin, I. J. Phys. Chem. A 1999, 103, 10274
51. Timoneda, J. J. I.; Hynes, J. T. J. Phys. Chem. 1991, 95, 10431
52. Mulliken, R. S.; Rieke, C. A.; Orloff, D.; Orloff, H. J. Chem. Phys. 1949, 17, 1248
53. Chandler, D. Introduction to Modern Statistical Mechanics; Oxford University Press: Oxford, 1987.
54. Berne, B. J.; Borkovec, M.; Straub, J. E. J. Phys. Chem. 1988, 92, 3711
55. Gertner, B. J.; Wilson, K. R.; Hynes, J. T. J. Chem. Phys. 1989, 90, 3537
56. Whitnell, R. M.; Wilson, K. R. Computational molecular dynamics of chemical reactions in solution. In Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; VCH: New York, 1993.
57. Nosé, S. J. Phys.: Condens. Matter 1991, 2, SA115
58. Allen, M. P.; Tildesley, D. J. Computer Simulation of Liquids; Clarendon: Oxford, 1987.
59. Uchiyama, Y.; Kitamori, T.; Sawada, T.; Tsuyumoto, I. Langmuir 2000, 16, 6597
60. King, G.; Warshel, A. J. Chem. Phys. 1990, 93, 8682
61. Carter, E. A.; Hynes, J. T. J. Chem. Phys. 1991, 94, 5961
62. Bergsma, J. P.; Gertner, B. J.; Wilson, K. R.; Hynes, J. T. J. Chem. Phys. 1987, 86, 1356
63. Gertner, B. J.; Bergsma, J. P.; Wilson, K. R.; Lee, S.; Hynes, J. T. J. Chem. Phys. 1987, 86, 1377