Steric, quantum, and electrostatic effects on SN2 reaction barriers in gas phase

Journal of Physical Chemistry A

Volumn 114, Issue 18, 2010, Pages 5913-5918

  Liu, Shubin ^a   Hu, Hao ^b   Pedersen, Lee G ^c,d  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

^c NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^d University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BARRIER HEIGHTS; BIO-MOLECULAR; CONVENTIONAL METHODS; ELECTROSTATIC EFFECT; ENERGY DECOMPOSITION; EXCHANGE-CORRELATIONS; FLUORINE ANIONS; GASPHASE; METHYL HALIDES; NATURAL BOND ORBITAL ANALYSIS; NUCLEOPHILIC SUBSTITUTION REACTIONS; QUANTUM EFFECTS; REACTION BARRIER HEIGHTS; REACTION BARRIERS; REACTION CENTER; RELATIVE CONTRIBUTION; STERIC EFFECT; STERIC HINDRANCES; TRANSITION STATE; WAVE FUNCTION THEORY;

CHEMICAL BONDS; ELECTROSTATICS; FLUORINE; GASES; ORGANIC POLYMERS; QUANTUM ELECTRONICS; SUBSTITUTION REACTIONS;

DENSITY FUNCTIONAL THEORY;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GAS; PHASE TRANSITION; QUANTUM THEORY; STATIC ELECTRICITY; THERMODYNAMICS;

GASES; MOLECULAR STRUCTURE; PHASE TRANSITION; QUANTUM THEORY; STATIC ELECTRICITY; THERMODYNAMICS;

EID: 77952157411     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp101329f     Document Type: Article

References (62)

1. Wade, L. G. Organic Chemistry, 5th ed.; Prentice Hall: Upper Saddle River, NJ, 2003.
2. N2 Mechanism; John Wiley & Sons: New York, 1992.
3. Steric Effects in Organic Chemistry; Newman, M. S., Ed.; John Wiley and Sons: New York, 1956.
4. Hughes, E. D.; Ingold, C. K. J. Chem. Soc. 1935, 244
5. Dostrovsky, I.; Hughes, E. D.; Ingold, C. K. J. Chem. Soc. 1946, 173
6. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: New York, 1988.
7. Ingold, C. K. Structure and Mechanism in Organic Chemistry, 2nd ed.; Cornell University Press: Ithaca, NY, 1969.
8. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper Collins: New York, 1987.
9. DeTar, D. F.; McMullen, D. F.; Luthra, N. P. J. Am. Chem. Soc. 1978, 100, 2484
10. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006.
11. Caldwell, G.; Magnera, T. F.; Kebarle, P. J. Am. Chem. Soc. 1984, 106, 959
12. Olmstead, W. N.; Brauman, J. I. J. Am. Chem. Soc. 1977, 99, 4219
13. Craig, S. L.; John, I.; Brauman, J. I. Science 1998, 276, 1536
14. Chabinyc, M. L.; Craig, S. L.; Regan, C. K.; Brauman, J. I. Science 1998, 279, 1882
15. Laerdahl, J. K.; Uggerud, E. Int. J. Mass. Spectrom. 2002, 214, 277
16. Regan, C. K.; Craig, S. L.; Brauman, J. I. Science 2002, 295, 2245
17. Jensen, F. Chem. Phys. Lett. 1992, 196, 368
18. Vayner, G.; Houk, K. N.; Jorgensen, W. L.; Brauman, J. I. J. Am. Chem. Soc. 2004, 126, 9054
19. Kim, Y.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. A 2009, 113, 9109
20. Chen, X.; Regan, C. K.; Craig, S. L.; Krenske, E. H.; Houk, K. N.; Jorgensen, W. L.; Brauman, J. I. J. Am. Chem. Soc. 2009, 131, 16162
21. Weisskopf, V. F. Science 1975, 187, 605
22. Badenhoop, J. K.; Weinhold, F. J. Chem. Phys. 1997, 107, 5406; Int. J. Quantum Chem. 1999, 72, 269
23. Liu, S. B. J. Chem. Phys. 2007, 126, 244103
24. March, N. H. Phys. Lett. A 1986, 113, 476
25. Levy, M.; Ou-Yang, H. Phys. Rev. A 1988, 38, 625
26. Herring, C.; Chopra, M. Phys. Rev. A 1988, 37, 31
27. Savin, A.; Becke, A. D.; Flad, J.; Nesper, R.; Preuss, H.; von Schnering, H. G. Angew. Chem., Int. Ed. 1991, 30, 409
28. Holas, A.; March, N. H. Phys. Rev. A 1991, 44, 5521
29. Levy, M.; Perdew, J. P. Phys. Rev. A 1985, 32, 2010
30. Liu, S. B.; Parr, R. G. Phys. Rev. A 1996, 53, 2211
31. Liu, S. B.; Karasiev, V.; Lopez-Boada, R.; De Proft, F. Int. J. Quantum Chem. 1998, 69, 513
32. Liu, S. B.; Nagy, A.; Parr, R. G. Phys. Rev. A 1999, 59, 1131
33. Nagy, A.; Liu, S. B.; Parr, R. G. Phys. Rev. A 1999, 59, 3349
34. Liu, S. B.; Morrison, R. C.; Parr, R. G. J. Chem. Phys. 2006, 125, 174109
35. Liu, S. B.; Parr, R. G. J. Phys. Chem. A 2007, 111, 10422
36. von Weizsäcker, C. F. Z. Phys. 1935, 96, 431
37. Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Oxford University Press: Oxford, 1990.
38. Liu, S. B.; Govind, N. J. Phys. Chem. A 2008, 112, 6690
39. Liu, S. B. J. Chem. Phys. 2007, 126, 191107
40. Liu, S. B.; Govind, N. L. G.; Pedersen, J. Chem. Phys. 2008, 129, 094104
41. Nagy, A.; Liu, S. B. Phys. Lett. A 2008, 372, 1654
42. Ugŭr, I.; Vleeschouwer, F. D.; Tüzün, N.; Aviyente, V.; Geerlings, P.; Liu, S. B.; Ayers, P. W.; De Proft, F. J. Phys. Chem. A 2009, 113, 8704
43. Taft, R. W., Jr. J. Am. Chem. Soc. 1952, 74, 2729
44. Torrent-Sucarrat, M.; Liu, S. B.; De Proft, F. J. Phys. Chem. A 2009, 113, 3698
45. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
46. Liu, S. B. Acta Phys.-Chim. Sin. 2009, 25, 590
47. Nagy, A. Chem. Phys. Lett. 2007, 449, 212
48. Becke, A. D. Phys. Rev. A 1988, 38, 3098; J. Chem. Phys. 1993, 98, 5648
49. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
50. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A., Gaussian 03, Rev E.02; Gaussian, Inc.: Wallingford, CT, 2004.
51. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49
52. Hratchian, H. P.; Schlegel, H. B. J. Chem. Phys. 2004, 120, 9918
53. Straatsma, T. P.; Aprȧ, E.; Windus, T. L.; Bylaska, E. J.; de Jong, W.; Hirata, S.; Valiev, M.; Hackler, M.; Pollack, L.; Harrison, R.; Dupuis, M.; Smith, D. M. A.; Nieplocha, J.; Tipparaju, V.; Krishnan, M.; Auer, A. A.; Brown, E.; Cisneros, G.; Fann, G.; Früchtl, H.; Garza, J.; Hirao, K.; Kendall, R.; Nichols, J.; Tsemekhman, K.; Wolinski, K.; Anchell, J.; Bernholdt, D.; Borowski, P.; Clark, T.; Clerc, D.; Dachsel, H.; Deegan, M.; Dyall, K.; Elwood, D.; Glendening, E.; Gutowski, M.; Hess, A.; Jaffe, J.; Johnson, B.; Ju, J.; Kobayashi, R.; Kutteh, R.; Lin, Z.; Littlefield, R.; Long, X.; Meng, B.; Nakajima, T.; Niu, S.; Rosing, M.; Sandrone, G.; Stave, M.; Taylor, H.; Thomas, G.; van Lenthe, J.; Wong, A.; Zhang, Z. NWChem, A Computational Chemistry Package for Parallel Computers, Version 4.6; Pacific Northwest National Laboratory: Richland, Washington 99352-0999, 2004.
54. Kendall, R. A.; Aprȧ, E.; Bernholdt, D. E.; Bylaska, E. J.; Dupuis, M.; Fann, G. I.; Harrison, R. J.; Ju, J.; Nichols, J. A.; Nieplocha, J.; Straatsma, T. P.; Windus, T. L.; Wong, A. T. High Performance Computational Chemistry: An Overview of NWChem, a Distributed Parallel Application Comput. Phys. Comm. 2000, 128, 260
55. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0. Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2001.
56. Glukhovtsev, M. N.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1995, 117, 2024
57. Glad, S. S.; Jensen, F. J. Am. Chem. Soc. 1997, 119, 227
58. Deng, L.; Branchadell, V.; Ziegler, T. J. Am. Chem. Soc. 1994, 116, 10645
59. Rong, C.; Lian, S.; Yin, D.; Zhong, A. G.; Zhang, R. Q.; Liu, S. B. Chem. Phys. Lett. 2007, 434, 149
60. Rong, C.; Lian, S.; Yin, D.; Shen, B.; Zhong, A. G.; Bartolotti, L.; Liu, S. B. J. Chem. Phys. 2006, 125, 174102
61. Liu, S. B.; Pedersen, L. G. J. Phys. Chem. A 2009, 113, 3648
62. Liu, S. B.; Schauer, C. K.; Pedersen, L. G. J. Chem. Phys. 2009, 131, 164107