Using secondary α deuterium kinetic isotope effects to determine the symmetry of S(N)2 transition states

Journal of the American Chemical Society

Volumn 119, Issue 16, 1997, Pages 3670-3676

  Westaway, Kenneth Charles ^a   Van Pham, Thuy ^a   Fang, Yao Ren ^a  

^a LAURENTIAN UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE; ORGANIC COMPOUND;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; ISOTOPE LABELING; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030991937     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962088f     Document Type: Article

References (45)

1. Westaway, K. C.; Ali, S. F. Can. J. Chem. 1979, 57, 1354.
2. Westaway, K. C.; Waszczylo, Z. Can. J. Chem. 1982, 60, 2500.
3. Yamataka, H.; Ando, T. J. Am. Chem. Soc. 1979, 101, 266.
4. Harris, J. M.; Shafer, S. G.; Moffat, J. R.; Becker, A. R. J. Am. Chem. Soc. 1979, 101, 3295.
5. Lee, I. Chem. Soc. Rev. 1995, 223.
6. Wolfe, S.; Kim, C.-K. J. Am. Chem. Soc. 1991, 113, 8056.
7. Poirier, R. A.; Wang, Y.; Westaway, K. C. J. Am. Chem. Soc. 1994, 116, 2526,
8. Barnes, J. A.; Williams, I. H. J. Chem. Soc., Chem. Commun. 1993, 1286.
9. N2 processes.
10. Saunders, W. H. Chem. Scripta 1975, 8, 27.
11. 12
12. Smith, P. J.; Pollock, C. A.; Bourns, A. N. Can. J. Chem. 1975, 53, 1319.
13. Maccoll, A. Anna. Rep. A: Chem. Soc. (London) 1974, 71, 77.
14. Buddenbaum, W. E.; Shiner, V. J., Jr. In Isotope Effects on Enzyme-Catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: London, 1977; p 18.
15. α-H(D) out-of-plane bending vibrations in the transition state.
16. Hartshorn, S. R.; Shiner, V. J., Jr. J. Am. Chem. Soc. 1972, 94, 9002.
17. Shiner, V. J., Jr.; Neumann, T. E. Z. Naturforsch. 1989, 44a, 337.
18. N2 Processes In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C, Eds.; Elsevier: New York, 1987; Vol. 7, p 312.
19. Humski, K; Sendijarevic, V.; Shiner, V. J., Jr. J. Am. Chem. Soc. 1974, 96, 6187.
20. Westaway, K. C., Tetrahedron Lett. 1975, 4229.
21. N2 Processes In Isotopes in Organic Chemistry; Buncel E., Lee, C. C., Eds.; Elsevier: New York, 1987; Vol. 7, pp 311-316.
22. 1,2
23. Hoz, S.; Basch, S; Goldberg, M. J. J. Am. Chem. Soc. 1992, 114, 4364.
24. Stefanidis, D.; Jencks, W. P. J. Am. Chem. Soc. 1993, 115, 6045.
25. Lee, I.; Lee, W. H.; Lee, H. W. J. Phys. Org. Chem. 1990, 3, 545.
26. α-H(D) out-of-plane bending vibrations.
27. Westaway, K. C. Can. J. Chem. 1993, 71, 2084.
28. Matsson, O.; Persson, J.; Axelsson, B. S.; Långström, B.; Fang, Y.-R.; Westaway, K. C. J. Am. Chem. Soc: 1996, 118, 6350.
29. Hill, J. W.; Fry, A. J. Am. Chem. Soc. 1962, 84, 2763.
30. Fry, A. In Isotope Effects in Organic Reactions; Collins, C. J., Bowman, N. S., Eds.; ACS Publication 167; Van Nostrand Reinhold: New York, 1970; p 380.
31. N2 processes.
32. N2 Processes In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Ehevier New York, 1987; Vol. 7, pp 275-392.
33. Sims, L B ; Fry, A.; Netherton, L. T.; Wilson, J. C.; Reppond, K. D.; Crook, S. W. J. Am. Chem. Soc. 1972, 94, 1364
34. Gray, C. H.; Coward, J. K., Schowen, B. K.; Schowen, R. L. J. Am. Chem. Soc. 1979, 101, 4351.
35. Ashan, M.; Robertson, R. E.; Blandamer, M. J.; Scott, J. M. W. Can. J. Chem. 1980, 58, 2142.
36. Shiner, V. J.; Rapp, M. W.; Pinnick, H. R., Jr. J. Am. Chem. Soc. 1970, 92, 232.
37. Koshy, K. M.; Robertson, R. E. J. Am. Chem. Soc. 1974, 96, 914.
38. Vitullo, V. P.; Grabowski, J.; Sridharan, S. J. Am. Chem. Soc. 1980, 102, 6463.
39. Lee, I.; Koh, H. J.; Lee, B.-S.; Sohn, D. S.; Lee, B. C. J. Chem. Soc., Perkin Trans. 2 1991, 1741.
40. Ando, T.; Tanabe, H.; Yamataka, H. J. Am. Chem. Soc. 1984, 106, 2084.
41. Matsson, O.; Persson, J.; Fang, Y.-R.; Westaway, K. C. Unpublished results.
42. Westaway, K. C.; Koerner, T. Unpublished results.
43. Shriner, R. L.; Fuson, R. C.; Curtin, D. Y. In The Systematic Identification of Organic Compounds, 4th ed.; J. Wiley and Sons: New York, 1959; p 149.
44. Snyder, L. R.; Kirkland, J. J. In Introduction to Modern Liquid Chromatography, 2nd ed.; Wiley-Interscience: New York, 1979; pp 549-555.
45. Laidler, K. J. In Chemical Kinetics; McGraw-Hill Inc.: New York, 1965; p 8.