General acid-base catalysis of complex reactions in water

Chemical Reviews

Volumn 72, Issue 6, 1972, Pages 705-718

  Jencks, William P ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001329652     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr60280a004     Document Type: Article

References (67)

1. R. A. More O'Ferrall, J. Chem. Soc. B, 274 (1970).
2. C. G. Swain, D. A. Kuhn, and R. L. Schowen, J. Amer. Chem. Soc., 87, 1553 (1965).
3. J. E. Reimann and W. P. Jencks, J. Amer. Chem. Soc., 88, 3973 (1966).
4. R. L. Schowen, Progr. Phys. Org. Chem., 9, 275 (1972).
5. C. G. Swain and J. C. Worosz, Tetrahedron Lett., 36, 3199 (1965).
6. E. H. Cordes and W. P. Jencks, J. Amer. Chem. Soc., 84, 4319 (1962).
7. W. P. Jencks, Progr. Phys. Org. Chem., 2, 63 (1964).
8. G. S. Hammond, J. Amer. Chem. Soc., 77, 334 (1955).
9. G. E. Lienhard and W. P. Jencks, J. Amer. Chem. Soc., 88, 3982 (1966).
10. C. G. Swain and C. B. Scott, J. Amer. Chem. Soc.t 75, 141 (1953).
11. J. Hine, J. Amer. Chem. Soc., 94, 5766 (1972).
12. J. L. Kurz, J. Amer. Chem. Soc., 85, 987 (1963).
13. R. P. Bell, Adoan. Phys. Org. Chem., 4, 1 (1966).
14. Y. Ogata, A. Kawasaki, and N. Okumura, Tetrahedron, 22, 1731 (1966).
15. K. Dusek, Collect. Czech. Chem. Commun., 25, 108 (1960).
16. M. Eigen, Angew. Chem. Int. Ed. Engl., 3, 1 (1964).
17. R. E. Barnett and W. P. Jencks, J. Amer. Chem. Soc., 91, 2358 (1969).
18. W. P. Jencks, J. Amer. Chem. Soc., 94, 4731 (1972). The rule does not apply to certain diffusion-controlled reactions in which separate proton transfer steps are not possible. It does apply to the separate steps of reactions proceeding through intermediates so long as these intermediates have a significant lifetime; if there are no such intermediates it should be applied to the overall reaction.
19. W. P. Jencks, “Catalysis in Chemistry and Enzymology,” McGraw-Hill, New York, N. Y., 1969, Chapters 3 and 10.
20. J. Hine, J. Org. Chem., 31, 1236 (1966).
21. E. Sander and W. P. Jencks, J. Amer. Chem. Soc., 90, 4377 (1968).
22. J. Hine and F. C. Kokesh, J. Amer. Chem. Soc., 92, 4383 (1970);
23. J. Hine, J. C. Craig, Jr., J. G. Underwood, II, and F. A. Via, Amer. Chem. Soc., 92, 5194 (1970).
24. A. R. Fersht, Amer. Chem. Soc., 93, 3504 (1971).
25. J. P. Fox, M. I. Page, A. Satterthwait, and W. P. Jencks, Amer. Chem. Soc., 94, 4729 (1972).
26. M. Caplow, Amer. Chem. Soc., 90, 6795 (1968).
27. R. K. Chaturvedi and G. L. Schmir, Amer. Chem. Soc., 91, 737 (1969).
28. G. M. Blackburn, Chem. Commun., 249 (1970);
29. M. F. Aldersley, A. J. Kirby, and P. W. Lancaster, J. Chem. Soc., Chem. Commun., 570 (1972).
30. T. S.T. Pierre and W. P. Jencks, J. Amer. Chem. Soc., 90, 3817 (1968).
31. S. M. Felton and T. C. Bruice, J. Amer. Chem. Soc., 91, 6721 (1969).
32. J. E. Leffler, Science, 117, 340 (1953).
33. J. F. Bunnett, Sure. Progr. Chem., 5, 53 (1969).
34. E. R. Thornton, J. Amer. Chem. Soc., 89, 2915 (1967).
35. F. G. Bordwell, Accounts Chem. Res., 3, 281 (1970).
36. W. P. Jencks and K. Salvesen, J. Amer. Chem. Soc., 93, 1419 (1971).
37. L. D. Kershner and R. L. Schowen, J. Amer. Chem. Soc., 93, 2014 (1971).
38. J. E. Gordon, J. Org. Chem., 26, 738 (1961).
39. E. H. Cordes, Progr. Phys. Org. Chem., 4, 1 (1967).
40. G. C. Pimentel and A. L. McClellan, Annu. Rev. Phys. Chem., 22, 347 (1971).
41. M. M. Kreevoy and C. A. Mead, Discuss. Faraday Soc., 39, 166 (1965).
42. D. E. Irish and H. Chen, J. Phys. Chem., 74, 3796 (1970).
43. E. Grunwald and M. Cocivera, Discuss. Faraday Soc., 39, 105 (1965).
44. M. L. Ahrens and G. Maass, Angew. Chem. Int. Ed. Engl., 7, 818 (1968).
45. A. M. Katz and W. H. Saunders, Jr., J. Amer. Chem. Soc., 91, 4469 (1969).
46. F. H. Westheimer, Chem. Rev., 61, 265 (1961).
47. E. Grunwald, Progr. Phys. Org. Chem., 3, 317 (1965).
48. E. Clementi, J. Chem. Phys., 46, 3851 (1967);
49. C. D. Ritchie and H. F. King, J. Amer. Chem. Soc., 90, 825, 833, 838 (1968).
50. R. E. Barnett and W. P. Jencks, J. Amer. Chem. Soc., 91, 6758 (1969).
51. R. G. Kallen and W. P. Jencks, J. Biol. Chem., 241, 5851 (1966).
52. C. A. Bunton and R. H. DeWolfe, J. Org. Chem., 30, 1371 (1965).
53. D. R. Robinson and W. P. Jencks, J. Amer. Chem. Soc., 89, 7088 (1967).
54. J. M. Sayer and W. P. Jencks, J. Amer. Chem. Soc., 94, 3262 (1972).
55. R. P. Bell, J. P. Millington, and J. M. Pink, Proc. Roy. Soc., Ser. A, 303, 1 (1968).
56. G. E. Lienhard and F. H. Anderson, J. Org. Chem., 32, 2229 (1967).
57. B. A. Cunningham and G. L. Schmir, J. Amer. Chem. Soc., 88, 551 (1966).
58. S. O. Eriksson, Acta Chem. Scand., 22, 892 (1968).
59. M. Eigen, Discuss. Faraday Soc., 39, 7 (1965).
60. L. do Amaral, W. A. Sandström, and E. H. Cordes, J. Amer. Chem. Soc., 88, 2225 (1966).
61. T. H. Fife and L. K. Jao, J. Amer. Chem. Soc., 90, 4081 (1968).
62. E. Anderson and B. Capon, J. Chem. Soc. B, 1033 (1969).
63. R. H. DeWolfe, K. M. Ivanetich, and N. F. Perry, J. Org. Chem., 34, 848 (1969).
64. A. Kankaanperä and M. Lahti, Acta Chem. Scand., 23, 2465 (1969).
65. T. H. Fife and E. Anderson, J. Org. Chem., 36, 2357 (1971).
66. A. Kankaanperä, Acta Chem. Scancl., 23, 1723, 1728 (1969).
67. J. Critchlow, Faraday Trans. I, J. Chem. Soc., in press.