Influence of substituents on kinetic isotope effects

Journal of the American Chemical Society

Volumn 118, Issue 43, 1996, Pages 10577-10583

  Nielsen, Peter Aa ^b   Glad, Sanne S ^b   Jensen, Frank ^a  

^a UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CALCULATION; CHEMICAL REACTION KINETICS; ISOTOPE LABELING; MOLECULAR DYNAMICS; THEORY;

EID: 0029844520     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961501g     Document Type: Article

References (70)

1. Melander, L.; Saunders, W., Jr. Isotope effects on reaction rates; Wiley-Interscience: New York, 1980.
2. Westheimer, F. H. Chem. Rev. 1961, 61, 265-273.
3. (a) More O'Ferrall, R. A. J. Chem. Soc. B 1970, 785-790.
4. (b) More O'Ferrall, R. A. J. Chem. Soc. B 1967, 985-990.
5. Buncel, E.; Lee, C. C., Eds. Isotopes in organic chemistry; Elsevier: Amsterdam, 1976; Vol. 2.
6. Buncel, E.; Lee, C. C., Eds. Isotopes in organic chemistry; Elsevier: Amsterdam, 1987; Vol. 7.
7. Streitwieser, A., Jr.; Jagow, R. H.; Fahey. R. C.; Suzuki, S. J. Am. Chem. Soc. 1958. 80, 2326-2332.
8. (a) Zhao, X. G.; Tucker, S. C.; Truhlar, D. G. J. Am. Chem. Soc. 1991, 113, 826-832.
9. (b) Barnes, J. A.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1993, 1286-1287.
10. (c) Poirier, R. A.; Wang, Y.; Westaway, K. C. J. Am. Chem. Soc. 1994, 116, 2526-2533.
11. (a) Wolfe, S.; Kim, C.-K. J. Am. Chem. Soc. 1991, 113, 8056-8061.
12. (b) Boyd, R. J.; Kim, C.-K.; Shi, Z.; Weinberg, N.; Wolfe, S. J. Am. Chem. Soc. 1993. 115, 10147-10152.
13. (a) Bakke, J. M.; Frøhaug, A. E. Acta Chem. Scand. 1995, 49, 615-622.
14. (b) Bergman, N.-Å.; Källsson, I. Acta Chem. Scand. 1976, A30, 411-417.
15. (c) Hussénius, A.; Matsson, O. Acta Chem. Scand. 1990, 44, 845-850.
16. (d) Caulton, K. G.; Chisholm, M. H.; Streib, W. E.; Xue, Z. J. Am. Chem. Soc. 1991, 113, 6082-6090.
17. (e) Nguyen, M. T.; Clarke, L. F.; Hegarty, A. F. J. Org. Chem. 1990, 55, 6177-6183.
18. (f) Westaway, K. C. Can. J. Chem. 1993, 71, 2084-2094.
19. (g) Hengge, A. C.; Hess, R. A. J. Am. Chem. Soc. 1994, 116, 11256-11263.
20. (h) Moss, R. A.; Liu, W.; Krogh-Jespersen, K. Tetrahedron Lett. 1993, 38, 6025-6028.
21. (i) Zhang, Y.; Bommuswamy, J.; Sinnott, M. L. J. Am. Chem. Soc. 1994, 116, 7557-7563.
22. (a) Glad, S. S.; Jensen, F. J. Am. Chem. Soc. 1994, 116, 9302-9310.
23. (b) Glad, S. S.; Jensen, F. Submitted for publication.
24. (a) Houk, K. N.; Gustavson, S. M.; Black, K. A. J. Am. Chem. Soc. 1992, 114, 8565-8572.
25. (b) Yoo, H. Y.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10247-10248.
26. (c) Wiest, O.; Black. K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336-10337.
27. (d) Storer, J. W.; Raimondi, L.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 9675-9683.
28. (e) Olson, L. P.; Niwayama, S.; Yoo, H.-Y.; Houk, K. N.; Harris, N. J.; Gajewski, J. J. J. Am. Chem. Soc. 1996, 118, 886-892.
29. (f) Wiest, O.; Houk, K. N.; Black, K. A.; Thomas. B., IV J. Am. Chem. Soc. 1995, 117, 8594-8599.
30. (g) Olson, L. P.; Li, Y.; Houk. K. N. J. Am. Chem. Soc. 1995, 117, 2992-2997.
31. (a) Duan, X.; Scheiner, S. J. Am. Chem. Soc. 1992, 114, 5849-5856.
32. (b) Wilkie, J.; Williams, I. H. J. Am. Chem. Soc. 1992, 114, 5423-5425.
33. (c) Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487-7492, 1996, 118, 297.
34. (c) Jensen, F. J. Am. Chem. Soc. 1995, 117, 7487-7492, 1996, 118, 297.
35. Hu, W.-P.; Truhlar, D. G. J. Am. Chem. Soc. 1996, 118, 860-869.
36. (a) Garrett, B. C.; Truhlar, D. G. J. Am. Chem. Soc. 1980, 102, 2559-2570.
37. (b) Truhlar, D. G.; Isaacson, A. D.; Skodje, R. T.; Garrett, B. C. J. Phys. Chem. 1982, 86, 2252-2261.
38. (c) Tucker, S. C.; Truhlar, D. G.; Garrett, B. C.; Isaacson, A. D. J. Chem. Phys. 1985, 82, 4102-4119.
39. (d) Garrett, B. C.; Truhlar, D. G.; Schatz. G. C. J. Am. Chem. Soc. 1986, 108, 2876-2881.
40. (e) Kreevoy, M. M.; Ostovic, D.: Truhlar, D. G.; Garrett, B. C. J. Phys. Chem. 1986, 90, 3766-3774.
41. (f) Schwenke, D. W.; Tucker, S. C.; Steckler, R.; Brown, F. B.; Lynch. G. C.; Truhlar, D. G.; Garrett, B. C. J. Chem. Phys. 1989, 90, 3110-3120.
42. (g) Tucker, S. C.; Truhlar, D. G. J. Am. Chem. Soc. 1990, 112, 3338-3347.
43. (h) Lu, D.-R; Maurice, D.; Truhlar, D. G. J. Am. Chem. Soc. 1990, 112, 6206-6214.
44. (i) Liu, Y.-P.; Lu, D.-H.; Gonzalez-Lafont, A.; Truhlar, D. G.; Garrett, B. C. J. Am. Chem. Soc. 1993, 115, 7806-7822.
45. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: London, 1980.
46. (a) Saunders, W. H. Chem. Scr. 1976, 10, 82-89.
47. (b) Burton, G. W.; Sims, L. B.; McLennan, D. J. J. Chem. Soc., Perkin Trans. 2 1977, 1763-1770.
48. (e) Saunders, W. H., Jr. J. Am. Chem. Soc. 1985, 107, 164-169.
49. (d) Saunders, W. H., Jr. J. Am. Chem. Soc. 1986, 108, 2223-2224.
50. (e) Bach, R. D.; Gonzalez, C.; Andres, J. L.; Schlegel, H. B. J. Org. Chem. 1995, 60, 4653-4656.
51. Glad, S. S.; Jensen, F. J. Chem. Soc., Perkin Trans. 2 1994, 871-876.
52. Wolfe, S.; Kim, C.-K. Isr. J. Chem. 1993, 33, 295-305.
53. (a) Gaussian 92, Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1992.
54. (b) Gaussian 94, 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.; Closlowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; 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, Inc.: Pittsburgh, PA, 1995.
55. Glad, S. S.; Jensen, F. J. Phys. Chem. In press.
56. Glad, S. S.; Jensen, F. Submitted for publication.
57. - results would be displaced slightly toward the right in Figure 3.
58. (a) Gajewski, J. J.; Gee, K. R.; Jurayj, J. J. Org. Chem. 1990, 55, 1813-1822.
59. (b) Gajewski, J. J.; Hawkin, C. M.; Jimenes, J. L. J. Org. Chem. 1990, 55, 674-679.
60. (c) Harris, N. J.: Gajewski, J. J. J. Am. Chem. Soc. 1994, 116, 6121-6129.
61. (d) Gajewski, J. J.; Brichford, N. L. J. Am. Chem. Soc. 1994, 116, 3165-3166.
62. (e) Kupczyk-Subotkowska. L.; Saunders, W. H., Jr.; Shine, H. J.; Subotkowska, W. J. Am. Chem. Soc. 1994, 116, 7088-7093.
63. (c) Kupczyk-Subotkowska, L.; Saunders, W. H., Jr.; Shine, H. J.; Subotkowska, W. J. Am. Chem. Soc: 1993, 115, 5957-5961.
64. (g) Hengge, A. C.; Hess. R. A. J. Am. Chem. Soc. 1994, 116, 11256-11263.
65. (h) Gajewski, J. J.; Gee, K. R. J. Am. Chem. Soc. 1991, 113, 967-971.
66. (i) Gajewski, J. J.; Peterson, K. B.; Kagel, J. R.; Huang, Y. C. J. J. Am. Chem. Soc. 1989, 111, 9078-9081.
67. (j) Gajewski, J. J.; Peterson, K. B.; Kagel, J. R.; Huang, Y. C. J. J. Am. Chem. Soc. 1987, 109, 5545-5546.
68. (k) Gajewski, J. J.; Jimenez, J. L. J. Am. Chem. Soc. 1986, 108, 468-474.
69. (a) Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119.
70. (b) Peräkylä, M. J. Phys. Chem. 1996, 100, 3441-3447.