Steric retardation of SN2 reactions in the gas phase solution

Journal of the American Chemical Society

Volumn 126, Issue 29, 2004, Pages 9054-9058

  Vayner, Grigoriy ^a   Houk, K N ^a   Jorgensen, William L ^b   Brauman, John I ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b YALE UNIVERSITY   (United States)

^c STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CONTINUUM MECHANICS; DERIVATIVES; MONTE CARLO METHODS; ORGANIC COMPOUNDS; PHASE SHIFT; POLARIZATION; SOLVENTS; SUBSTRATES;

GAS-PHASE RATE; SOLVENT EFFECTS; STERIC EFFECTS;

CHLORIDE MINERALS;

BUTANE; CHLORIDE; CHLOROETHANE; METHYL GROUP; NEOPENTYL CHLORIDE; NITRILE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION; GAS; MODEL; SN2 REACTION; SOLVATION; STEREOCHEMISTRY;

EID: 3242807324     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049070m     Document Type: Article

References (48)

1. (a) Olmstead, W. N.; Brauman, J. I. J. Am. Chem. Soc. 1977, 99, 4219.
2. (b) Barfknecht, T.; Dodd, J. A.; Salomon, K. E.; Tumas, W. E.; Brauman, J. I. Pure Appl. Chem. 1984, 56, 1809.
3. (c) Caldweel. G.; Magnera, T. F.; Kebarle, P. J. Am. Chem. Soc. 1984, 106, 959.
4. For a recent review, see: Laerdahl, J. K.; Uggerud. E. Int. J. Mass Spectrom. 2002, 214, 277.
5. (a) Berthier, G.; David, D.-J.; Veillard, A. Theor. Chim. Acta 1969, 14, 329.
6. (b) Dedieu, A.; Veillard, A. Chem. Phys. Lett. 1970, 5, 328.
7. (c) Dedieu, A.; Veillard, A. J. Am. Chem. Soc. 1972, 94, 6730.
8. (d) Ritchie, C. D.; Chappel, G. A. J. Am. Chem. Soc. 1972, 92, 1819.
9. (e) Duke, A. J.; Bader, R. F. W. Chem. Phys. Lett. 1971, 10, 631.
10. (f) Gonzales, J. M.; Pak, C.; Cox, R. S.; Allen, W. D.; Schaefer, H. F.; Csaszar, A. G.; Tarczay, G. Chem.-Eur. J. 2003, 9, 2173.
11. Botchwina, P. Theor. Chem. Acc. 1998, 99, 426.
12. Based on the activation energies of unsymmetrical halogen exchange: McLennan, D. J. Aust. J. Chem. 1978, 31, 1897. Bathgate, R. H.; Moelwyn-Huges, E. A. J. Chem. Soc. 1959, 2694.
13. Based on the activation energies of unsymmetrical halogen exchange: McLennan, D. J. Aust. J. Chem. 1978, 31, 1897. Bathgate, R. H.; Moelwyn-Huges, E. A. J. Chem. Soc. 1959, 2694.
14. (a) Dostrovski, I.; Hughes, E. D. J. Chem. Soc. 1946, 157.
15. (b) Dostrovski, I.; Hughes, E. D.; Ingold, C. K. J. Chem. Soc. 1946, 173.
16. (c) de la Mare, P. B. D.; Fowden, L.; Hughes, E. D.; Ingold, C. K.; Mackie, J. D. H. J. Chem. Soc. 1955, 3200.
17. Brown, W. H.; Foote C. S. Organic Chemistry, 3rd ed.; Saunders College Publishers: New York; p 283.
18. Vollhardt, K. P. C.; Schore, N. E. Organic Chemistry Structure and Function, 4th ed.; Freeman and Co.: New York; p 235.
19. March, J. Advanced Organic Chemistry Reactions, Mechanisms, and Structure, 4th ed.; John Wiley and Sons: New York; pp 275, 339.
20. Regan, C. K.; Craig, S. L.; Brauman, J. I. Science 2002, 296, 2245.
21. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
22. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
23. Montgomery, J. A., Jr.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Tornasi, L.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
25. Repasky, M. P.; Chandrasekhar, J.; Jorgensen, W. L. J. Comput. Chem. 2002, 23, 1601. Tubert-Brohman, I.; Guimaraes, C. R. W.; Repasky, M. P.; Jorgensen, W. L. J. Comput. Chem. 2004, 25, 138.
26. Repasky, M. P.; Chandrasekhar, J.; Jorgensen, W. L. J. Comput. Chem. 2002, 23, 1601. Tubert-Brohman, I.; Guimaraes, C. R. W.; Repasky, M. P.; Jorgensen, W. L. J. Comput. Chem. 2004, 25, 138.
27. Martin, J. M. L.; De Oliveira, G. J. Chem. Phys. 1999, 111, 1843.
28. Parthiban, S.; De Oliveira, G.; Martin, J. M. L. J. Phys. Chem. A 2001, 105, 895.
29. Chandrasekhar, J.; Shariffskul, S.; Jorgensen, W. L. J. Phys. Chem. B 2002, 106, 8078.
30. Kaminski, G. A.; Jorgensen, W. L. J. Phys. Chem. B 1998, 102, 1787.
31. Repasky, M. P.; Guimaraes, C. R. W.; Chandrasekhar, J.; Tirado-Rives, J.; Jorgensen, W. L. J. Am. Chem. Soc. 2003, 125, 6663.
32. Guimaraes, C. R. W.; Repasky, M. P.; Chandrasekhar, J.; Tirado-Rives, J.; Jorgensen, W. L. J. Am. Chem. Soc. 2003, 125, 6892.
33. Thompson, J. D.; Cramer, C. J.; Truhlar, D. G. J. Comput. Chem. 2003, 24, 1291.
34. Jorgensen, W. L. BOSS 4.5; Yale University: New Haven, 2003.
35. (a) Murphy, K. P.; Xie, D.; Thompson, K. S.; Amsel, L. M.; Freire, E. Proteins: Struct., Funct., Genet. 1994, 18, 63.
36. (b) Hermans, J.; Wang, L. J. Am. Chem. Soc. 1997, 119, 2707.
37. (a) Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995.
38. (b) Barone, B.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404.
39. Albery, W. J.; Kreevoy, M. M. Adv. Phys. Org. Chem. 1978, 16, 87.
40. DeTar, D.; McMullen, D. F.; Luthra, N. P. J. Am. Chem. Soc. 1978, 100, 2484.
41. Kondo, Y.; Siotani, H.; Kusabayashi, S. J. Chem. Soc., Faraday Trans. 1 1984, 80, 2145.
42. Chandrasekhar, J.; Smith, S. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 154.
43. Landini, D.; Maia, A.; Montanari, F.; Rolla, F. J. Org. Chem. 1983, 48, 3774.
44. Alexander, R.; Ko, E. C. F.; Parker, A. J.; Broxton, T. J. J. Am. Chem. Soc. 1968, 90, 5049.
45. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 5th ed.; Wiley: New York, 2001; p 432.
46. Hase, W. L. Science 1994, 266, 998.
47. Craig, S. L.; Brauman, J. I. Science 1997, 276, 1536. Viggiano, A. A.; Morris, R. A.; Su, T.; Wladkowski, B. D.; Craig, S. L.; Zhong, M.; Brauman. J. I. J. Am. Chem. Soc. 1994, 116, 2213.
48. Craig, S. L.; Brauman, J. I. Science 1997, 276, 1536. Viggiano, A. A.; Morris, R. A.; Su, T.; Wladkowski, B. D.; Craig, S. L.; Zhong, M.; Brauman. J. I. J. Am. Chem. Soc. 1994, 116, 2213.