The Nature and Analysis of Substituent Electronic Effects

Progress in Physical Organic Chemistry

Volumn 12, Issue , 2007, Pages 1-20

  Topsom, R D ^a  

^a LA TROBE UNIVERSITY   (Australia)

Author keywords

Dual substituent parameter (DSP) approach; Electronic substituent effect; Remote P system; Substituent electronic effects; Substituted systems

Indexed keywords

DUAL SUBSTITUENT PARAMETERS; ELECTRONIC EFFECTS; P SYSTEMS; SUBSTITUENT EFFECT;

EID: 84986617286     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470171912.ch1     Document Type: Chapter

References (81)

1. See, for example: J. Hine, Structural Effects on Equilibria in Organic Chemistry, Wiley, New York, 1975.
2. K. F. Johnson, The Hammen Equation, Cambridge, 1973.
3. P. R. Wells, Linear Free Energy Relationships, Academic Press, New York, 1968.
4. O. Exner, in Advances in Linear Free Energy Relationships, N. B. Chapman and J. Shorter, Eds., Plenum Press, London, 1972, Chapter 1.
5. S. Ehrenson, Prog. Phys. Org. Chem., 2, 195 (1964).
6. C. D. Ritchie and W. F. Sager, Prog. Phys. Org. Chem., 2, 323 (1964).
7. P. R. Wells, S. Ehrenson, and R. W. Taft, Prog. Phys. Org. Chem., 6, 147 (1968).
8. R. T. C. Brownlee, S. Ehrenson, and R. W. Taft, Prog. Phys. Org. Chem., 10, 1 (1973).
9. A. R. Katritzky and R. D. Topsom, Angew. Chem. Int. Ed. Engl., 9, 87 (1970).
10. A. R. Katritzky and R. D. Topsom, J. Chem. Educ, 48, 427 (1971).
11. R. T. C. Brownlee and R. W. Taft, J. Amer. Chem. Soc, 90, 6537 (1968).
12. R. T. C. Brownlee and R. W. Taft, J. Amer. Chem. Soc. 92, 7007 (1970).
13. W. J. Hehre, R. W. Taft, and R. D. Topsom, Prog. Phys. Org. Chem., 12,(1976).
14. T. B. Grindley, A. R. Katritzky, and R. D. Topsom, J. Chem. Soc, Perkin II. 1974, 289.
15. G. P. Ford, A. R. Katritzky, and R. D. Topsom, J. Chem. Soc. Perkin II. 1975, 1378.
16. See Refs. 1, 2, and 7 for earlier discussion.
17. See also G. K. Hamer, I. R. Peat, and W. F. Reynolds, Can. J. Chem. 51, 897 (1973).
18. W. F.Reynolds, I. R. Peat, M. H. Freedman, and J. R.Lyerla, Can. J. Chem. 51, 1857, (1973).
19. For a thorough coverage of earlier work see L. M. Stock, J. Chem. Educ. 49, 400 (1972).
20. I. Mochida and Y. Yoneda, Bull. Chem. Soc. Jap. 41, 1479 (1968).
21. W. A. Waters, J. Chem. Soc. 1933, 1551.
22. J. N. Murreil, S. F. A. Kettle, and J. M. Tedder, Valence Theory, Wiley, New York, 1965.
23. J. A. Pople and M. Gordon, J. Amer. Chem. Soc. 89, 4253 (1967).
24. W. J. Hehre and J. A. Pople, J. Amer. Chem. Soc. 92, 2191 (1970).
25. For example, while ,3C studies for some protonated amines might be so interpreted [I. Morishima, K. Yoshikawa, K. Okada, T. Yonezawa, and K. Goto, J. Amer. Chem. Soc. 95, 165 (1973)], there seems no evidence for such an effect from 13C studies of substituted alkanes (G. Miyajima and K. Nishimoto, Org. Magn. Resonance. 6, 313 (1974)).
26. T. W. Cole, C. J. Mayers, and L. M. Stock, J. Amer. Chem. Soc. 96, 4555 (1974).
27. F. W. Baker, R. C. Parish, and L. M. Stock, J. Amer. Chem. Soc. 89, 5477 (1967).
28. R. Golden and L. M. Stock, J. Amer. Chem. Soc. 94, 3080 (1972).
29. C. L. Liotta, private communication.
30. N. Inamoto, K. Kushida, S. Masuda, H. Ohta, S. Satoh, Y. Tamura, K. Tokumaru, K. Tori, and M. Yoshida, Tetrahedron Lett., 3617 (1974).
31. J. S. Sandhu and D. Mago, Tetrahedron Lett. 1975, 1091.
32. W. Henderson, W. Sheppard, and R. W. Taft, private communication.
33. See, for example: C. L. Liotta, W. F. Fisher, G. H. Greene, and B. L. Joyner, J. Amer. Chem. Soc. 94, 4891 (1972).
34. C. L. Liotta, W. F. Fisher, E. L. Slighton, and C. L. Harris, J. Amer. Chem. Soc. 94, 2129 (1972).
35. R. B. Herman, J. Amer. Chem. Soc. 91, 3152 (1969).
36. R. T. C. Brownlee and R. D. Topsom, Tetrahedron Lett. 1972, 5187.
37. Certainly charge densities do not always parallel stabilities; see, for example, J. F. Wolf, P. G. Hanch, R. W. Taft, and W. J. Hehre, J. Amer. Chem. Soc. 97, 2902 (1975).
38. R. T. C. Brownlee, G. Butt, C. H. Chan, and R. D. Topsom, J. Chem. Soc, Perkin II, in press.
39. See, for example, the following and the references therein: W. Adcock, M. Aurangzeb, W. Kitching, N. Smith, and D. Doddrell, Aust. J. Chem. 27, 1817 (1974).
40. W. Adcock, M. J. S. Dewar, and B. D. Gupta, J. Amer. Chem. Soc. 95, 7353 (1973).
41. G. L. Anderson, R. C. Parish, and L. M. Stock, J. Amer. Chem. Soc, 93,6984 (1971).
42. V. V. Zverov, Zh. Obshch. Khim. 40, 1891 (1970).
43. R. T. C. Brownlee, R. E. J. Hutchinson, A. R. Katritzky, T. T. Tidwell, and R. D. Topsom, J. Amer. Chem. Soc. 90, 1757 (1968).
44. W. A. Sheppard and R. M. Henderson, J. Amer. Chem. Soc. 89, 4446, (1967).
45. M. J. S. Dewar and Y. Takeuchi, J. Amer. Chem. Soc. 89, 390 (1967).
46. S. K. Dayal, S. Ehrenson and R. W. Taft, J. Amer. Chem. Soc. 94, 9113 (1972).
47. J. P. Idroux, V. S. Cantwell, J. Hinton, S. O. Nelson, P. Hollier, and R. Zavillo, J. Org. Chem. 39, 3946(1974).
48. P. J. Mitchell and L. Phillips, J. Chem. Soc, Perkin II. 1974, 109.
49. W. A. Sheppard, J. Amer. Chem. Soc. 87, 2410 (1965).
50. Although theoretical calculations do suggest that some change of electron population in the opposite sense occurs at the meta positions (see, for example Ref. 10).
51. W. Adcock, M. J. S. Dewar, and B. D. Gupta, J. Amer. Chem. Soc. 95, 7353 (1973).
52. L. Libit and R. Hoffmann, J. Amer. Chem. Soc. 96, 1370 (1974).
53. W. J. Hehre, L. Radom, and J. A. Pople, J. Amer. Chem. Soc. 94, 1496 (1972).
54. D. T. Clark, J. N. Murrell, and J. M. Tedder, J. Chem. Soc. 1963, 1250.
55. J. Burdon, Tetrahedron. 21, 3373 (1965).
56. D. P. Craig and G. Doggett, Mol. Phys. 8, 485, (1964).
57. D. T. Clark, Chem. Commun. 1966, 390.
58. See for example: R. T. C. Brownlee, D. G. Cameron, R. D. Topsom, A. R. Katritzky, and A. F. Pozharsky, J. Chem. Soc, Perkin II. 1974, 247 and references therein.
59. T. J. Broxton, G. Butt, R. Liu, L. H. Teo, R. D. Topsom, and A. R. Katritzky, J. Chem. Soc, Perkin II. 1974, 463.
60. M. A. Davis, J. Org. Chem. 32, 1161 (1967).
61. See, for example: R. T. C. Brownlee, J. Munday, R. D. Topsom, and A. R. Katritzky, J. Chem. Soc, Faraday 2, 1973, 349.
62. A. R. Katritzky, R. F. Pinzelli, M. V. Sinnott, and R. D. Topsom, J. Amer. Chem. Soc. 92, 6861 (1970).
63. T. B. Grindley, K. F. Johnson, A. R. Katritzky, H. J. Keogh, C. Thirkettle, R. T. C. Brownlee, J. A. Munday, and R. D. Topsom, J. Chem. Soc, Perkin II. 1974, 276.
64. A. R. Katritzky and R. D. Topsom, in Advances in Linear Free Energy Relationships, N. B. Chapman and J. Shorter, Eds., Plenum Press, London, 1972, Chapter 3.
65. C. G. Swain and E. C. Lupton, J. Amer. Chem. Soc. 90, 4328 (1968).
66. Y. Yukawa and Y. Tsuno, Bull. Chem. Soc. Jap. 32, 965, 971 (1959).
67. G. Thirot, Bull. Soc. Chim. (Fr.). 1967, 739.
68. M. J. S. Dewar and P. J. Grisdale, J. Amer. Chem. Soc. 84, 3539 (1962).
69. R. T. C. Brownlee and R. D. Topsom, Spectrochim. Acta, 29A, 385 (1973).
70. R. T. C. Brownlee and R. D. Topsom, Spectrochim. Acta, 31 A, 1677 (1975).
71. R. T. C. Brownlee, J. Di Stefano, and R. D. Topsom, Spectrochim. Acta, 31 A, 1685 (1975).
72. M. Sjostrom and S. Wold, Chem. Scr. 6, 114 (1974).
73. R. W. Taft and I. C. Lewis, J. Amer. Chem. Soc. 80, 2436 (1958).
74. R. W. Taft and C. A. Grob, J. Amer. Chem. Soc. 96, 1236(1974).
75. D. A. Dawson, G. K. Hamer, and W. F. Reynolds, Can. J. Chem. 52, 39 (1974).
76. D.A. Dawson and W. F. Reynolds, Can. J. Chem. 53, 373 (1975).
77. For a wide coverage see Ref. 5; for naphthalene data see Ref. 4; for extended systen Ref. 31; for uv data see Ref. 47; for infrared data see Refs. 48 and 54; for theoretici culations and nmr data see Refs. 10, 52, and 55.
78. L. W. Deady, A. R. Katritzky, R. Shanks, and R. D. Topsom, Spectrochim. Acta, 115 (1973).
79. R. T. C. Brownlee and J. Bromilow, Tetrahedron Lett. 1975, 2113.
80. R. W. Taft and R. D. Topsom, work in progress.
81. A. J. Hoefnagel and B. M. Wepster, J. Amer. Chem. Soc. 95, 5357 (1973).