An approach for assessing the relative importance of field and σ inductive contributions to polar substituent effects based on the nonproportionality of field and σ inductive substituent constants

Journal of the Chemical Society, Perkin Transactions 2

Volumn , Issue 7, 1980, Pages 985-991

  Reynolds, William F ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049110333     PISSN: 1472779X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29800000985     Document Type: Article

References (76)

1. L. M. Stock, J. Chem. Educ., 1972, 49, 400.
2. R. D. Topsom, Progr. Phys. Org. Chem., 1976, 12, 1.
3. J. M. Rees, J. H. Ridd, and A. Ricci, J.C.S. Perkin II, 1976, 224.
4. S. Acevedo and K. Bowden, J.C.S. Chem. Comm., 1977, 608.
5. N. Bjerrum, Z. Phys. Chem., 1923, 106, 219.
6. A. Eucken, Angew. Chem., 1932, 45, 203.
7. J. G. Kirkwood and F. H. Westheimer, J. Chem. Phys., 1938, 6, 506.
8. F. H. Westheimer and J. G. Kirkwood, J. Chem. Phys., p. 513.
9. A. D. Buckingham, Canad. J. Chem., 1960, 38, 300.
10. P. R. Wells, Progr. Phys. Org. Chem., 1968, 6, 111.
11. R. T. C. Brownlee and R. W. Taft, J. Amer. Chem. Soc., 1970, 92, 7007.
12. W. F. Reynolds, P. G. Mezey, and G. K. Hamer, Canad. J. Chem., 1977, 55. 522.
13. B. G. Ramsay, J. Organometallic Chem., 1977, 135, 307.
14. J. G. Batchelor, J. Feeney, and G. C. K. Roberts, J. Magnetic Resonance, 1975, 20, 19.
15. G. E. K. Branch and M. Calvin, ‘The Theory of Organic Chemistry,’ Prentice-Hall, New York, 1941.
16. J. N. Murrell, S. F. A. Kettle, and J. M. Tedder, ‘Valence Theory,’ Wiley, New York, 1965.
17. L. Pauling, ‘The Nature of the Chemical Bond,’ Cornell University Press, Ithaca, 1960, 3rd edn.
18. W. J. Hehre and J. A. Pople, J. Amer. Chem. Soc., 1970, 92, 2191.
19. R. W. Taft in ‘Steric Effects in Organic Chemistry,’ ed. M. S. Newman, Wiley, New York, 1956.
20. C. W. N. Cumper, Tetrahedron, 1969, 25, 3131.
21. A. L. McClellan, ‘Tables of Experimental Dipole Moments,’ Freeman, San Francisco, 1963.
22. B. L. Poh, Austral. J. Chem., 1979, 32, 427 and references therein.
23. W. J. Hehre, R. F. Stewart, and J. A. Pople, J. Chem. Phys., 1969, 51, 2657.
24. P. G. Mezey and W. F. Reynolds, Canad. J. Chem., 1977, 55, 1567.
25. M. Taagepera, W. J. Hehre, R. D. Topsom, and R. W. Taft, J. Amer. Chem. Soc., 1976, 98, 7438.
26. N. Inamota and S. Masuda, Tetrahedron Letters, 1977, 3287.
27. N. Inamoto and S. Masuda, Chem. Letters, 1978, 177.
28. J. D. Roberts and W. T. Moreland, J. Amer. Chem. Soc., 1953, 75, 2167.
29. H. D. Holtz and L. S. Stock, J. Amer. Chem. Soc., 1964, 86, 5188.
30. C. F. Wilcox and J. S. McIntyre, J. Org. Chem., 1965, 30, 777.
31. E. Ceppi, W. Eckhardt, and C. A. Brob, Tetrahedron Letters, 1973 3627.
32. W. Adcock and T. C. Khor, Tetrahedron Letters, 1976, 3063.
33. J. Amer. Chem. Soc., 1978, 100, 7799.
34. D. F. Ewing, S. Sotheeswaran, and K. J. Toyne, Tetrahedron Letters, 1977, 2041.
35. D. F. Ewing and K. J. Toyne, J.C.S. Perkin II, 1979, 243.
36. H. H. Jaffé, Chem. Rev., 1953, 53, 191.
37. J. Fukunaga and R. W. Taft, J. Amer. Chem. Soc., 1975, 97, 1612 and references therein.
38. W. Adcock and D. B. Gupta, J. Amer. Chem. Soc., 1975, 97, 6871 and references therein.
39. W. F. Reynolds and G. K. Hamer, J. Amer. Chem. Soc., 1976, 98 7296.
40. W. Kitching, M. Bullpitt, D. Gartshore, W. Adcock, T. C. Khor, D. Dodrell, and I. D. Rae, J. Org. Chem., 1977, 42, 2411.
41. W. F. Reynolds, I. R. Peat, M. H. Freedman, and J. R. Lyerla, Canad. J. Chem., 1973, 51, 1857.
42. H. K. Hall, J. Amer. Chem. Soc., 1957, 79, 5441.
43. P. Ballinger and F. A. Long, J. Amer. Chem. Soc., 1960, 82. 795.
44. M. Charton, J. Org. Chem., 1964, 29, 1222.
45. R. W. Taft, M. Taagepera, J. L. M. Abboud, J. F. Wolf, D. J. Defrees, W. J. Hehre, J. E. Bartmess, and R. T. McIver, J. Amer. Chem. Soc., 1978, 100, 7765.
46. J. I. Brauman and J. K. Blair, J. Amer. Chem. Soc., 1968, 90, 5636, 6501.
47. G. Kortüm, W. Vogel, and K. Aldrussow, Pure Appl. Chem., 1960, 1, 189.
48. A. A. Cheremisin and P. V. Schastnev, Z. Strukt. Khim., 1979, 20, 221.
49. O. Exner, in ‘Advances in Linear Free Energy Relationships,’ eds. N. B. Chapman and J. Shorter, Plenum Press, New York, 1972.
50. S. Ehrenson, R. T. C. Brownlee, and R. W. Taft, Progr. Phys. Org. Chem., 1973, 10, 1.
51. R. A. McClellan and W. F. Reynolds, Canad. J. Chem., 1977, 55, 536.
52. D. F. Ewing in ‘Correlation Analysis in Chemistry,’ eds. N. B. Chapman and J. Shorter, Plenum Press, New York, 1978.
53. C. D. Schaeffer, J. J. Zuckerman, and C. H. Yoder, J. Organometallic Chem., 1974, 80, 29.
54. R. H. Kohler, M.Sc. Thesis, University of Toronto, Toronto, 1975.
55. M. J. Shapiro, Tetrahedron, 1977, 33, 1091.
56. I. R. Peat, Ph.D. Thesis, University of Toronto, Toronto, 1973.
57. STPRG, IBM System 360 Scientific Subroutine package III.
58. R. W. Taft, personal communication.
59. R. W. Taft and C. A. Grob, J. Amer. Chem. Soc., 1974, 96, 1236.
60. A. J. Hoefnagel, M. A. Hoefnagel, and B. M. Wepster, J. Org. Chem., 1978, 43, 4720.
61. C. Tanford, J. Amer. Chem. Soc., 1957, 79, 5348.
62. C. L. Liotta, W. F. Fisher, E. L. Slightom, and C. L. Harris, J. Amer. Chem. Soc., 1971, 94, 2121.
63. S. Ehrenson, J. Amer. Chem. Soc., 1976, 98, 7510.
64. C. T. Want and E. T. Grubbs, J. Org. Chem., 1977, 42, 534.
65. R. B. Hermann, J. Amer. Chem. Soc., 1969, 91, 3152.
66. K. Hiraoka, R. Yamdagni, and P. Kebarle, J. Amer. Chem. Soc., 1973, 95, 6833.
67. M. Taagepera, W. G. Henderson, R. T. C. C. Brownlee, J. L. Beauchamp, D. Holtz, and R. W. Taft, J. Amer. Chem. Soc., 1972, 94, 1369.
68. R. B. McMahon and P. Kebarle, J. Amer. Chem. Soc., 1977, 99, 2222.
69. R. Yamdagni, T. B. McMahon, and P. Kebarle, J. Amer. Chem. Soc., 1974, 96, 4035.
70. W. F. Reynolds, T. A. Modro, and P. G. Mezey, J.C.S. Perkin II, 1977, 1066.
71. R. W. Taft, J. F. Wolf, J. L. Beauchamp, G. Scorrano, and E. M. Arnett, J. Amer. Chem. Soc., 1978, 100, 1240.
72. R. W. Taft in ‘Kinetics in Ion-Molecule Reactions,’ NATO Advanced Study Institute Series (B-Physics), ed. P. Ausloos, Plenum Press, New York, 1979, vol. 40, p. 271.
73. R. Golden and L. M. Stock, J. Amer. Chem. Soc., 1972, 94, 3080.
74. K. Bowden, M. Hardy, and D. C. Parkin, Canad. J. Chem., 1968, 46. 2929.
75. K. Bowden and D. C. Parkin, Canad. J. Chem., 1969, 47, 185.
76. R. T. Morrison and R. N. Boyd, ‘Organic Chemistry,’ Allyn and Bacon, Boston, 1973, 3rd edn.