A Primer for the Bema Hapothle. An Empirical Approach to the Characterization of Changing Transition-State Structures

Chemical Reviews

Volumn 85, Issue 6, 1985, Pages 511-527

  Jencks, William P ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3042520570     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr00070a001     Document Type: Review

References (92)

1. Wilputte-Steinert, L.; Fierens, P. J. C.; Hannaert, H. Bull. Soc. Chim. Belg. 1955, 64, 628. Ritchie, C. D.; Saltiel, J. D.; Lewis, E. S. J. Am. Chem. Soc. 1961, 83, 4601.
2. Miller, S. I. J. Am. Chem. Soc. 1959, 81, 101.
3. Cordes, E. H.; Jencks, W. P. J. Am. Chem. Soc. 1962, 84, 4319.
4. Jencks, D. A.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99. 7948.
5. Dubois, J.-E.; Ruasse, M.-F. Argile, A. J. Am. Chem. Soc. 1984, 106, 4840.
6. Kemp, D. S.; Casey, M. L. J. Am. Chem. Soc. 1973, 95, 6670.
7. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
8. Marcus, R. A. J. Phys. Chem. 1968, 72, 891.
9. Bell, R. P. Proc. R. Soc. London, Ser. A 1936, 154, 414. Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1938, 34,11. Leffler, J. E. Science (Washington, D.C.) 1953,117, 340. Leffler, J. E.; Grunwald, E. "Rates and Equilibria of Organic Reactions"; Wiley: New York, 1963; pp 128-170.
10. Thornton, E. R. J. Am. Chem. Soc. 1967, 89, 2915. Thornton, E. K.; Thornton, E. R. In "Transition States of Biochemical Processes"; Gandour, R. D., Schowen, R. L., Eds.; Plenum Press: New York, 1978; p 3.
11. Johnston, H. S. "Gas Phase Reaction Rate Theory"; Ronald Press: New York, 1966.
12. Harris, J. C.; Kurz, J. L. J. Am. Chem. Soc. 1970, 92, 349.
13. Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410. Agmon, N.; Levine, R. D. Chem. Phys. Lett. 1977, 52, 197. le Noble, W. J.; Miller, A. R.; Hamann, S. D. J. Org. Chem. 1977, 42, 338. Miller, A. R. J. Am. Chem. Soc. 1978,100,1984. Agmon, N.; Levine, R. D. J. Chem. Phys. 1979, 71, 3034. Lewis, E. S.; Shen, C. C.; More O'Ferrall, R. A. J. Chem. Soc, Perkin Trans. 2 1981, 1084.
14. Hanson, J. B.; Jencks, W. P., unpublished work. The acronym Mabe Hapothle may be more appropriate but was rejected as being insufficiently positive.
15. Ritchie, C. D. Acc. Chem. Res. 1972, 5, 348. Johnson, C. D. Chem. Rev. 1975, 75, 755. Giese, B. Angew. Chem., Int. Ed. Engl. 1977,16,125. Pross, A. Adv. Phys. Org. Chem. 1977,14, 69. Johnson, C. D. Tetrahedron 1980, 36, 3461.
16. Bordwell, F. G.; Hughes, D. L. J. Org. Chem. 1980, 45, 3320.
17. Young, P. R.; Jencks, W. P. J. Am. Chem. Soc. 1979, 101, 3288.
18. Albery, W. J. Annu. Rev. Phys. Chem. 1980, 31, 227.
19. Murdoch, J. R. J. Am. Chem. Soc. 1980, 102, 71.
20. Murdoch, J. R. J. Phys. Chem. 1983, 87, 1571. Murdoch, J. R. J. Am. Chem. Soc. 1983, 105, 2667.
21. Hughes, E. D.; Ingold, C. K.; Shapiro, U. G. J. Chem. Soc. 1936, 225.
22. Bunnett, J. F. Angew. Chem., Int. Ed. Engl. 1962, 1, 225.
23. More O'Ferrall, R. A. J. Chem. Soc. B 1970, 274.
24. Albery, W. J. Prog. React. Kinet. 1967, 4, 355. Gandour, R. D.; Maggiora, G. M.; Schowen, R. L. J. Am. Chem. Soc. 1974, 96, 6967. Cox, M. M.; Jencks, W. P. J. Am. Chem. Soc. 1981,103, 580.
25. Grunwald, E. J. Am. Chem. Soc. 1985, 107, 125.
26. See, for example, Rogne, O. J. Chem. Soc. B 1971, 1855.
27. Pross, A.; Shaik, S. S. Acc. Chem. Res. 1983, 16, 363.
28. Agmon, N. J. Am. Chem. Soc. 1984, 106, 6960.
29. Bell, R. P. J. Chem. Soc, Faraday Trans. 2 1976, 72, 2088. Saunders, W. H., Jr. J. Phys. Chem. 1982,86, 3321. Murdoch, J. R. J. Am. Chem. Soc. 1983,105, 2159.
30. Wiseman, F.; Kestner, N. R. J. Phys. Chem. 1984, 88, 4354.
31. Kurz, J. L. Chem. Phys. Lett. 1978, 57, 243.
32. Bordwell, F. G.; Boyle, W. J., Jr. J. Am. Chem. Soc. 1972, 94, 3907.
33. Pross, A. J. Org. Chem. 1984, 49, 1811.
34. Guthrie, J. P. J. Am. Chem. Soc. 1980, 102, 5286.
35. Hine, J. J. Am. Chem. Soc. 1959, 81, 1126.
36. Swain, C. G.; Langsdorf, W. P., Jr. J. Am. Chem. Soc. 1951, 73, 2813.
37. Critchlow, J. E. J. Chem. Soc, Faraday Trans. 1 1972, 68, 1774. Dunn, B. M. Int. J. Chem. Kinet. 1974, 6,143. Gajew-ski, J. J. J. Am. Chem. Soc. 1979, 101, 4393. Murdoch, J. R. J. Am. Chem. Soc. 1983,105, 2660. Gajewski, J. J.; Gilbert, K. E. J. Ore. Chem. 1984, 49, 11.
38. Albery, W. J.; Kreevoy, M. M. Adv. Phys. Org. Chem. 1978, 16, 87.
39. Kreevoy, M. M.; Lee, I.-S.H. J. Am. Chem. Soc 1984, 106, 2550.
40. Shiner, V. S.: Seib, R. C. J. Am. Chem. Soc 1976, 98, 862.
41. Harris, J. M.; Shafer, S. G.; Moffatt, J. R.; Becker, A. R. J. Am. Chem. Soc, 1979, 101, 3295.
42. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc 1984, 106, 1383.
43. Hudson, R. F.; Klopman, G. J. Chem. Soc 1962, 1062. Ballistreri, F. P.; Maccarone, E.; Mamo, A. J. Org. Chem. 1976, 41, 3364.
44. Westaway, K. C.: Waszczylo, Z. Can. J. Chem. 1982, 60, 2500.
45. Shiner, V. J., Jr.; Rapp, M. W.; Pinnick, H. R., Jr. J. Am. Chem. Soc. 1970, 92, 232. Koshy, K. M.; Robertson, R. E. Can. J. Chem. 1974,52, 2485. Ando, T.; Tanabe, H.; Yamataka, H. J. Am. Chem. Soc. 1984, 106, 2084.
46. Arnett, E. M.; Reich, R. J. Am. Chem. Soc. 1978, 100, 2930. Lewis, E. S.; Kukes, S.; Slater, C. D. J. Am. Chem. Soc. 1980, 102, 1619.
47. Kirby, A. J.; Varvoglis, A. G. J. Chem. Soc. B 1968, 135. Jameson, G. W.; Lawlor, J. M. J. Chem. Soc. B 1970, 53.
48. Skoog, M. T.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 7597.
49. Bourne, N.; Williams, A. J. Am. Chem. Soc. 1983, 105, 3357.
50. Jencks, W. P. Chem. Rev. 1972, 72, 705.
51. Gilbert, H. F.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 7931. This refers to the absence of curvature in Br⊘nsted plots when general acid catalysis of the addition step itself is rate limiting. With some nucleophilic reagents there is a concurrent stepwise mechanism with rate-limiting proton transfer and catalysis by trapping of the anionic addition intermediate, which gives nonlinear Br⊘nsted plots.56
52. Funderburk, L. H.; Aldwin, L.; Jencks, W. P. J. Am. Chem. Soc 1978, 100, 5444.
53. Sorensen, P. E.; Jencks, W. P., in preparation.
54. Grunwald, E. J. Am. Chem. Soc 1985, 107, 4710, 4715.
55. Saunders, W. J., Jr.; Cockerill, A. F. "Mechanisms of Elimination Reactions"; Wiley: New York, 1973. Winey, D. A.; Thornton, E. R. J. Am. Chem. Soc. 1975, 97, 3102.
56. Smith, P. J.; Bourns, A. N. Can. J. Chem. 1974, 52, 749.
57. Fry, A. Chem. Soc. Rev. 1972, 1, 163.
58. Gandler, J. R.; Jencks, W. P. J. Am. Chem. Soc. 1982, 104, 1937.
59. Gandler, J. R.; Yokoyama, T. J. Am. Chem. Soc. 1984, 106, 130.
60. Thibblin, A. Chem. Scr. 1980, 15, 121.
61. Hasan, T.; Sims, L. B.; Fry, A. J. Am. Chem. Soc, 1983, 105, 3967.
62. Sayer, J. M.; Jencks, W. P. J. Am. Chem. Soc 1977, 99, 464.
63. Sayer, J. M.; Peskin, M.; Jencks, W. P. J. Am. Chem. Soc. 1973, 95, 4277.
64. Fife, T. H. Acc. Chem. Res. 1972, 5, 264.
65. Gravitz, N.; Jencks, W. P. J. Am. Chem. Soc. 1974, 96, 507.
66. Capon, B.; Nimmo, K. J. Chem. Soc, Perkin Trans. 2 1975, 1113.
67. Bernasconi, C. F.; Gandler, J. R. J. Am. Chem. Soc 1978, 100, 8117.
68. Bergstrom, R. G.; Cashen, M. J.; Chiang, Y.; Kresge, A. J. J. Org. Chem. 1979, 44, 1639.
69. Jensen, J. L.; Herold, L. R.; Lenz, P. A.; Trusty, S.; Sergi, V.; Bell, K.; Rogers, P. J. Am. Chem. Soc. 1979, 101, 4672.
70. Palmer, J. L.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 6466.
71. Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1984, 106, 1396.
72. Palmer, J. L.; Jencks, W. P. J. Am. Chem. Soc 1980, 102, 6472.
73. Eliason, R.; Kreevoy, M. M. J. Am. Chem. Soc. 1978, 700, 7037.
74. Bunton, C. A.; De Wolfe, R. H. J. Org. Chem. 1965, 30, 1371.
75. Fife, T. H.; Anderson, E. J. Am. Chem. Soc. 1970, 92, 5464.
76. Jensen, J. L.; Jencks, W. P. J. Am. Chem. Soc. 1979, 101, 1476.
77. Cordes, E. H.; Bull, H. G. Chem. Rev. 1974, 74, 581.
78. Jencks, W. P. Acc. Chem. Res. 1976, 9, 425.
79. Thibblin, A.; Jencks, W. P. J. Am. Chem. Soc. 1979, 101, 4963.
80. Johnson, S. L.; Morrison, D. L. J. Am. Chem. Soc 1972, 94, 1323.
81. Ewing, S. P.; Lockshon, D.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 3072.
82. Young, P. R.; Jencks, W. P. J. Am. Chem. Soc. 1978, 100, 1228.
83. Kreevoy, M. M.; Liang, T.-M.; Chang, K.-C. J. Am. Chem. Soc. 1977, 99, 5207.
84. Sayer, J. M.; Jencks, W. P. J. Am. Chem. Soc. 973, 95, 5637.
85. Bernasconi, C. F. Tetrahedron 1985, 41, 3219.
86. Richard, J. P.; Rothenberg, M. E.; Jencks, W. P. J. Am. Chem. Soc 1984, 106, 1361.
87. Kresge, A. J. Can. J. Chem. 1974, 52, 1897.
88. Hupe, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 451. Hupe, D. J.; Wu, D. J. Am. Chem. Soc. 1977, 99, 7653. Jencks, W. P.; Brant, S. R.; Gandler, J. R.; Fendrich, G.; Nakamura, C. J. Am. Chem. Soc. 1982, 104, 7045.
89. Jencks, W. P.; Nazaretian, K.; Herschlag, D.; Haber, M. J. Am. Chem. Soc, in press.
90. Stahl, N.; Jencks, W. P. in preparation.
91. Funderburk, L. H.; Jencks, W. P. J. Am. Chem. Soc. 1978, 100, 6708, footnote 26. See also ref 5.
92. Rothenberg, R.; Richard, J. P.; Jencks, W. P. J. Am. Chem. Soc. 1985, 107, 1340.