Normal acid/base behaviour in proton transfer reactions to alkoxy substituted carbenes: Estimates for intrinsic barriers to reaction and pK(a) values

Canadian Journal of Chemistry

Volumn 77, Issue 7, 1999, Pages 1230-1240

  Pezacki, John Paul ^a,b  

^a MCMASTER UNIVERSITY   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

Bronsted plots; Carbenes; Carbocations; Marcus theory; Proton transfer reactions

Indexed keywords

CARBENE;

ACID BASE BALANCE; AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; PROTON TRANSPORT; REACTION ANALYSIS; REACTION TIME; THERMODYNAMICS;

EID: 0033306384     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v99-087     Document Type: Article

References (100)

1. 1. (a) R.P. Bell. The proton in chemistry. 2nd ed. Cornell University Press, Ithaca, N.Y. 1973;
2. (b) A.J. Kresge. Chem. Soc. Rev. 4, 475 (1973);
3. (c) In Proton transfer reactions. Edited by E.F. Caldin and V. Gold. Chapman and Hall, London. 1975. Chap. 7;
4. (d) W.P. Jencks. Acc. Chem. Res. 9, 425 (1976);
5. (e) A.J. Kresge. Acc. Chem. Res. 8, 354 (1975);
6. (e) J. Hine. Adv. Phys. Org. Chem. 15, 1 (1977);
7. (f) C.F. Bernasconi. Acc. Chem. Res. 25, 9 (1992);
8. (g) Adv. Phys. Org. Chem. 27, 119 (1991);
9. (h) Acc. Chem. Res. 20, 301 (1987).
10. 2. (a) M.T. Emerson, E. Grunwald, M.L. Kaplan, and R.A. Kromhout. J. Am. Chem. Soc. 82, 6307 (1960);
11. (b) E. Grunwald. J. Phys. Chem. 67, 2211 (1963);
12. (c) E. Grunwald and E.K. Ralph. Acc. Chem. Res. 4, 107 (1971);
13. (d) E. Grunwald and D. Eustace. In Proton transfer reactions. Edited by E.F. Caldin and V. Gold. Chapman and Hall, London. 1975. pp. 103-120.
14. 3. J.P. Guthrie. J. Am. Chem. Soc. 118, 12886 (1996), and refs. therein.
15. 4. M. Eigen. Angew. Chem. Int. Ed. Engl. 3, 1 (1964).
16. 5. W. Kirmse. In Advances in carbene chemistry. Edited by U. Brinker. JAI Press Inc., London. 1994. pp. 1-57, and refs. therein.
17. 6. (a) S.T. Belt, C. Bohne, G. Charette, S.E. Sugamori, and J.C. Scaiano. J. Am. Chem. Soc. 115, 2200 (1993);
18. (b) E.J. Dix and J.L. Goodman. J. Phys. Chem. 98, 12609 (1994);
19. (c) W. Kirmse, B. Krzossa, and S. Steenken. J. Am. Chem. Soc. 118, 7473 (1996);
20. (d) J.E. Chateauneuf. J. Chem. Soc. Chem. Commun. 1437 (1991);
21. (e) W. Kirmse, J. Kilian, and S. Steenken. J. Am. Chem. Soc. 112, 6399 (1990).
22. 7. (a) W. Kirmse, K. Loosen, and H.-D. Sluma. J. Am. Chem. Soc. 103, 5935 (1981);
23. (b) W. Kirmse and H.-D. Sluma. J. Org. Chem. 53, 763 (1988).
24. 8. W. Kirmse, T. Meinert, D.A. Modarelli, and M.S. Platz. J. Am. Chem. Soc. 115, 8918 (1993).
25. 9. (a) A.J. Arduengo III, J.R. Goerlich, and W.J. Marshall. J. Am. Chem. Soc. 117, 11027 (1995);
26. (b) G. Boche, C. Hilf, K. Harms, M. Marsch, and J.C.W. Lohrenz. Angew. Chem. Int. Ed. Engl. 34, 487 (1995);
27. (c) M.K. Denk, A. Thadani, K. Hatano, and A.J. Lough. Angew. Chem. Int. Ed. Engl. 36, 2607 (1997).
28. 10. (a) R.W. Hoffmann, B. Hagenbruch, and D.M. Smith. Chem. Ber. 110, 23 (1977);
29. (b) H.A. Staab, H. Irngartinger, A. Mannschreck, and M.-T. Wu. Justus Liebigs Ann. Chem. 55 (1966);
30. (c) G. Scherowsky, K. Dünnbier, and G. Höfle. Tetrahedron Lett. 2095 (1977);
31. (d) R.A. Olofson and J.M. Landesberg. J. Am. Chem. Soc. 88, 4263 (1966);
32. (e) R.A. Olofson, J.M. Landesberg, K.N. Houk, and J.S. Michelman. J. Am. Chem. Soc. 88, 4265 (1966);
33. (f) G. Scherowsky. Chem. Ber. 107, 1092 (1974);
34. (g) A.J. Arduengo III, J.R. Goerlich, and W.J. Marshall. Liebigs Ann. Chem. 365 (1997).
35. 11. (a) R. Breslow. J. Am. Chem. Soc. 79, 1762 (1957);
36. (b) R. Kluger. Chem. Rev. 87, 863 (1987).
37. 12. F.G. Bordwell and A.V. Satish. J. Am. Chem. Soc. 113, 985 (1991).
38. 13. M.W. Washabaugh and W.P. Jencks. J. Am. Chem. Soc. 111, 674 (1989); 111, 683 (1989).
39. 14. M.W. Washabaugh and W.P. Jencks. Biochemistry, 27, 5044 (1988).
40. 15. R.W. Alder, P.R. Alien, and S.J. Williams. J. Chem. Soc. Chem. Commun. 1267 (1995).
41. 16. N.G. Rondan, K.N. Houk, and R.A. Moss. J. Am. Chem. Soc. 102, 1770 (1980).
42. 17. R.A. Moss, M. Wostowski, S. Shen, K. Krogh-Jespersen, and A. Matro. J. Am. Chem. Soc. 110, 4443 (1988).
43. 18. (a) R.W. Hoffmann. Acc. Chem. Res. 18, 248 (1985);
44. (b) R.W. Hoffmann, B. Hagenbruch, and D.M. Smith. Chem. Ber. 110, 23 (1977);
45. (c) W. Lilienblum and R.W. Hoffmann. Chem. Ber. 110, 3405 (1977);
46. (d) R.W. Hoffmann and M. Reiffen. Chem. Ber. 109, 2565 (1976);
47. (e) R.A. Moss and J.K. Huselton. J. Chem. Soc. Chem. Commun. 950 (1976);
48. (f) R.W. Hoffmann, K. Steinbach, and W. Lilienblum. Chem. Ber. 109, 1759 (1976);
49. (g) R.W. Hoffmann, W. Lilienblum, and B. Dittrich. Chem. Ber. 107, 3395 (1974);
50. (h) R.W. Hoffmann, K. Steinbach, and B. Dittrich. Chem. Ber. 106, 2174 (1973);
51. (i) R.W. Hoffmann. Angew. Chem. Int. Ed. Engl. 10, 529 (1971);
52. (j) R.W. Hoffmann and C. Wunsche. Chem. Ber. 100, 943 (1967);
53. (k) D.M. Lemal, E.P. Gosselink, and S.D. McGregor. J. Am. Chem. Soc. 88, 582 (1966);
54. (l) D.M. Lemal, R.W. Lovald, and R.W. Harrington. Tetrahedron Lett. 2779 (1965);
55. (m) R.W. Hoffmann and H. Hauser. Tetrahedron, 21, 891 (1965);
56. (n) Tetrahedron Lett. 197 (1964);
57. (o) D.M. Lemal, E.P. Gosselink, and A. Ault. Tetrahedron Lett. 579 (1964).
58. 19. (a) M. El-Saidi, K. Kassam, D.L. Pole, T. Tadey, and J. Warkentin. J. Am. Chem. Soc. 114, 8751 (1992);
59. (b) K. Kassam, D.L. Pole, M. El-Saidi, and J. Warkentin. J. Am. Chem. Soc. 116, 1161 (1994);
60. (c) W.W. Win, M. Kao, M. Eiermann, J.J. McNamara, F. Wudl, D.L. Pole, K. Kassam, and J. Warkentin. J. Org. Chem. 59, 5871 (1994);
61. (d) J.D. Colomvakos, I. Egle, J. Ma, D.L. Pole, T.T. Tidwell, and J. Warkentin. J. Org. Chem. 61, 9522 (1996);
62. (e) A. de Meijere, S.I. Kozhushkov, D.S. Yufit, R. Boese, T. Haumann, D.L. Pole, P.K. Sharma, and J. Warkentin. Liebigs Ann. Chem. 601 (1996);
63. (f) D. L. Pole and J. Warkentin. Liebigs Ann. 1907 (1995);
64. (g) J. Org. Chem. 62, 4065 (1997);
65. (h) P. Couture, D.L. Pole, and J. Warkentin. J. Chem. Soc. Perkin Trans. 2, 1565 (1997).
66. 20. (a) C.-S. Ge, E.A. Jefferson, and R.A. Moss. Tetrahedron Lett. 34, 7549 (1993);
67. (b) R.A. Moss, M. Wostowski, J. Terpinski, G. Kmiecik-Lawrynowicz, and K. Krogh-Jespersen. J. Am. Chem. Soc. 109, 3811 (1987);
68. (c) X.-M. Du, H. Fan, J.L. Goodman, M.A. Kesselmayer, K. Krogh-Jespersen, J.A. LaVilla, R.A. Moss, S. Shen, and R.S. Sheridan. J. Am. Chem. Soc. 112, 1920 (1990);
69. (d) R.A. Moss, M. Wostowski, S. Shen, K. Krogh-Jespersen, and A. Matro. J. Am. Chem. Soc. 110, 4443 (1988);
70. (e) R.A. Moss, S. Shen, and M. Wostowski. Tetrahedron Lett. 29, 6417 (1988).
71. 21. R.A. Moss and D. P. Cox. Tetrahedron Lett. 26, 1931 (1985).
72. 22. J.A. Dunn, J.P. Pezacki, M.J. McGlinchey, and J. Warkentin. J. Org. Chem. 64, 4344 (1999).
73. 23. J. Warkentin. In Advances in carbene chemistry. Edited by U. Brinker. JAI Press Inc., Greenwich, Conn. 1998. pp. 245-295.
74. 24. (a) P. Ballinger and F.A. Long. J. Am. Chem. Soc. 82, 795 (1960);
75. (b) B.L. Dyatkin, E.P. Mochalina, and I.L. Knunyants. Tetrahedron, 21, 2991 (1965);
76. (c) S. Takahashi, L.A. Cohen, H.K. Miller, and E.G. Peake. J. Org. Chem. 36, 1205 (1971).
77. 25. The IUPAC Chemical Data Series. No. 35, 1990 (compiled by K. Izutsu).
78. 26. G.S. Hammond. J. Am. Chem. Soc. 77, 334 (1955).
79. 27. R.A. Marcus. J. Phys. Chem. 72, 891 (1968).
80. 28. (a) J.P. Pezacki, B.D. Wagner, C.S.Q. Lew, J. Warkentin, and J. Lusztyk. J. Am. Chem. Soc.119, 1789 (1997);
81. (b) Y. Chiang, A.S. Grant, A.J. Kresge, and S.W. Paine. J. Am. Chem. Soc. 118, 4366 (1996);
82. (c) W.J. Albery, A.J. Campbell-Crawford, and J.S. Curran. J. Chem. Soc. Perkin Trans. 2, 2206 (1972);
83. (d) A.J. Kresge. Chem. Soc. Rev. 4, 475 (1973).
84. 29. (a) H. Fischer, F.X. DeCandis, S.D. Ogden, and W.P. Jencks. J. Am. Chem. Soc. 102, 1340 (1980);
85. (b) H.F. Gilbert and W.P. Jencks. J. Am. Chem. Soc. 99, 7931 (1977);
86. (c) R.A. Bednar and W.P. Jencks. J. Am. Chem. Soc. 107, 7117 (1985).
87. 30. J.R. Murdoch. J. Am. Chem. Soc. 102, 71 (1980).
88. 31. (a) J.A. Elvidge, J.R. Jones, C. O'Brien, E.A. Evans, and H.C. Sheppard. Adv. Heterocycl. Chem. 16, 1 (1974);
89. (b) J.H. Ridd. Phys. Methods Heterocycl. Chem. 4, 55 (1971).
90. 32. R.A. McClelland, M.J. Kahley, P.A. Davidse, and G. Hadzialic. J. Am. Chem. Soc. 118, 4794 (1996).
91. 33. C.J. Murray and W.P. Jencks. J. Am. Chem. Soc. 112, 1880 (1990).
92. 34. A.G. Brook. In The chemistry of organic silicon compounds. Edited by S. Patai and Z. Rappoport. Wiley, New York. 1989. Chap. 15, and refs. therein.
93. 35. (a) H.M. Perrin, W.R. White, and M.S. Platz. Tetrahedron Lett. 32, 4443 (1991);
94. (b) W. Kirmse, M. Guth, and S. Steenken. J. Am. Chem. Soc.118, 10838 (1996).
95. 36. (a) A.G. Brook, R. Kiviskk, and G.E. Legrow. Can. J. Chem. 43, 1175 (1965);
96. (b) A.G. Brook and J.B. Pierce. J. Org. Chem. 30, 2566 (1965).
97. 37. J.W. Larson and T.B. McMahon. J. Am. Chem. Soc. 109, 6230 (1987).
98. 38. A.J. Kresge and M.F. Powell. J. Org. Chem. 51, 819 (1986); 51, 822 (1986).
99. 39. (a) J.T. Stivers and M.W. Washabaugh. Bioorg. Chem.19, 369 (1991);
100. (b) R. Kluger, J.F. Lam, J.P. Pezacki, and C.-M. Yang. J. Am. Chem. Soc. 117, 11383 (1995).