Linear solvation energy relationships. Part 37. An analysis of contributions of dipolarity-polarisability, nucleophilic assistance, electrophilic assistance, and cavity terms to solvent effects on t-butyl halide solvolysis rates

Journal of the Chemical Society, Perkin Transactions 2

Volumn , Issue 7, 1987, Pages 913-920

  Abraham, Michael H ^a   Doherty, Ruth M ^b   Kamlet, Mortimer J ^b   Harris, J Milton ^c   Taft, Robert W ^d  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b NAVAL SURFACE WARFARE CENTER   (United States)

^c UNIVERSITY OF ALABAMA IN HUNTSVILLE   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049076695     PISSN: 1472779X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p29870000913     Document Type: Article

References (48)

1. E. Grunwald and S. Winstein, J. Am. Chem. Soc., 1948, 70, 846
2. S. Winstein and E. Grunwald, J. Am. Chem. Soc., 1951, 73, 2700
3. A. H. Fainberg and S. Winstein, J. Am. Chem. Soc., 1956, 78, 2770.
4. D. J. Raber, R. C. Bingham, J. M. Harris, J. L. Fry, and P. von R. Schleyer, J. Am. Chem. Soc., 1970, 92, 5977.
5. T. W. Bentley and P. von R. Schleyer, Adv. Phys. Org. Chem., 1977, 14, 1.
6. I. A. Koppel and V. A. Palm, Adv. Linear Free Energy Relationships, 1972, 203.
7. M. H. Abraham, R. W. Taft, and M. J. Kamlet, J. Org. Chem., 1981, 46, 3053.
8. C. G. Swain, M. S. Swain, A. L. Powell, and S. Alunni, J. Am. Chem. Soc., 1983, 105, 502.
9. M. J. Kamlet, J-L. M. Abboud, M. H. Abraham, and R. W. Taff, J. Org. Chem., 1983, 48, 2877.
10. M. J. Kamlet, P. W. Carr, R. W. Taft, and M. H. Abraham, J. Am. Chem. Soc., 1981, 103, 6062.
11. M. H. Abraham, M. J. Kamlet, and R. W. Taft, J. Chem. Soc., Perkin Trans. 2, 1982, 923.
12. M. H. Abraham and R. J. Abraham, J. Chem. Soc., Perkin Trans. 2, 1974, 47.
13. T. W. Bentley and G. E. Carter, J. Am. Chem. Soc., 1882, 104, 5741.
14. T. W. Bentley, G. E. Carter, and K. Roberts, J. Org. Chem., 1984, 49, 5183.
15. J. M. Harris, D. I. Mount, M. R. Smith, W. C. Neal Jr., M. D. Dukes, and D. J. Raber, J. Am. Chem. Soc., 1978, 100, 8147.
16. D. N. Kevill, W. A. Kamil, and S. W. Anderson, Tetrahedron Lett., 1982, 23, 4635.
17. D. Farcasiu, J. Jahme and C. Ruchardt, J. Am. Chem. Soc., in the press.
18. J. H. Hildebrand and R. L. Scott, ‘The Solubility of Nonelectrolytes,’ 3rd edn., Dover, New York.
19. R. W. Taft, M. H. Abraham, R. M. Doherty, and M. J. Kamlet, J. Am. Chem. Soc., 1985, 107, 3105.
20. E. Matteoli, Z. Phys. Chem. (Wiesbaden), 1980, 123, 141.
21. J. V. Leyendekkers, J. Chem. Soc., Faraday Trans. 1, 1982, 78, 357.
22. M. H. Abraham and A. Nasehzadeh, unpublished work
23. M. H. Abraham and A. Nasehzadeh, J. Chem. Soc., Chem. Commun., 1981, 905.
24. S. Cabani, G. Conti, E. Matteoli, and M. R. Tine, J. Chem. Soc., Faraday Trans, 1, 1981, 77, 2377.
25. G. A. Clarke and R. W. Taft, J. Am. Chem. Soc., 1962, 84, 2295.
26. M. H. Abraham, J. Chem. Soc., Perkin Trans. 2, 1972, 1343.
27. M. H. Abraham, Prog. Phys. Org. Chem., 1974, 11, 1.
28. G. F. Dvorko, E. A. Ponomareva, and N. I. Kulik, Russ. Chem. Rev., 1984, 53, 547.
29. M. H. Abraham, J. Chem. Soc., Faraday Trans. 1, 1973, 69, 1375.
30. P. Kebarle, Ann. Rev. Phys. Chem., 1977, 28, 445.
31. W. L. Jorgensen and J. R. Monroe, J. Am. Chem. Soc., 1978, 100, 1511
32. W. L. Jorgensen, J. Am. Chem. Soc., 1977, 99, 280
33. W. L. Jorgensen, J. Am. Chem. Soc., 1978, 100, 1049.
34. D. J. Raber, W. C. Neal Jr., M. D. Dukes, J. M. Harris, and D. L. Mount, J. Am. Chem. Soc., 1978, 100, 8137
35. J. B. Lambert and R. B. Finzel, J. Am. Chem. Soc., 1983, 105, 1954
36. V. J. Shiner and R. D. Rutkowsky, Abstracts 187th A.C.S. National Meeting, St Louis, Mo., April 8–13, 1984, ORGN 061
37. D. J. McLennan and P. L. Martin, J. Chem. Soc., Perkin Trans. 2, 1982, 1091.
38. S. P. McManus, N. Neamati-Mazraeh, B. H. Hovanes, and J. M. Harris, J. Am. Chem. Soc., 1985, 107, 3393.
39. R. M. Doherty, J. M. Harris, M. H. Abraham, R. W. Taft, and M. J. Kamlet, J. Org. Chem., in the press.
40. R. H. Staley, R. D. Weiting, and J. C. Beauchamp, J. Am. Chem. Soc., 1977, 99, 5964.
41. D. Mirda, D. Rapp, and G. M. Kramer, J. Org. Chem., 1979, 44, 2619.
42. E. M. Arnett, C. Petro, and P. von R. Schleyer, J. Am. Chem. Soc., 1979, 101, 522.
43. J. M. Harris, Prog. Phys. Org. Chem., 1974, 11, 89.
44. J. M. Harris and S. P. McManus, J. Am. Chem. Soc., 1974, 96, 4693.
45. C. Reichardt, ‘Solvent Effects in Organic Chemistry,’ Verlag Chemie, Weinheim, 1979, ch. 7.
46. T. W. Bentley and K. Roberts, J. Org. Chem., 1985, 50, 4821.
47. M. H. Abraham, R. M. Doherty, M. J. Kamlet, J. M. Harris, and R. W. Taft, in the press.
48. M. H. Abraham, Pure Appi. Chem., 1985, 57, 1055.