An unusual ground-state stabilization effect and origins of the α- effect in aminolyses of Y-substituted phenyl X-substituted benzoates

Canadian Journal of Chemistry

Volumn 76, Issue 6, 1998, Pages 729-737

  Um, Ik Hwan ^a   Chung, Eun Kyung ^a   Lee, So Mi ^a  

^a Ewha Womans University   (South Korea)

Author keywords

Ground state stabilization effect; Intramolecular H bonding interaction; effect

Indexed keywords

BENZENE DERIVATIVE; BENZOIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR STABILITY; REACTION ANALYSIS;

EID: 0031765069     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/cjc-76-6-729     Document Type: Article

References (63)

1. T.H. Lowry and K.S. Richardson. In Mechanism and theory in organic chemistry. 3rd ed. Harper Collins Publishers, New York. 1987. pp. 289-290.
2. J.O. Edwards and R.G. Pearson. J. Am. Chem. Soc. 84, 16 (1962).
3. (a) N.J. Fina and J.O. Edwards. Int. J. Chem. Kinet. 5, 1 (1973);
4. (b) A.P. Grekov and V.Y. Veselov. Usp. Khim. 47, 1200 (1978);
5. (c) E. Buncel and S. Hoz. Isr. J. Chem. 26, 313 (1985).
6. (a) F. Terrier, G. Moutiers, L. Xiao, E.L. Guevel, and F. Guir. J. Org. Chem. 60, 1974 (1995);
7. (b) F. Terrier, P. MacCormack, E. Kizilian, J.C. Halle, P. Demerseman, F. Guir, and C. Lion. J. Chem. Soc. Perkin Trans. 2, 153 (1991);
8. (c) F. Degorre, D. Kiffer, and F. Terrier. J. Med. Chem. 31, 757 (1988);
9. (d) K.R. Fountain, K.L. Hutchinson, D.C. Mulhearn, and Y.B. Xu. J. Org. Chem. 58, 7883 (1993);
10. (e) K.R. Fountain. D.P. Fountain, B. Michales, D.B. Myers, J.K. Salmon, D.A. Van Galen, and P Yu. Can. J. Chem. 69, 798 (1991);
11. (f) K.R. Fountain and K.D. Patel. J. Org. Chem. 62, 4795 (1997);
12. (g) K.R. Fountain, T.W. Dunkin, and K.D. Patel. J. Org. Chem. 62, 2738 (1997);
13. (h) O.A. El Seoud and M.F. Martins. J. Phys. Org. Chem. 8, 637 (1995);
14. (i) R.A. Hess, A.C. Hengge, and W.W. Cleland. J. Am. Chem. Soc. 119, 6980 (1997).
15. (a) E. Buncel, C. Chuagui, and H. Wilson. Int. J. Chem. Kinet. 14, 823 (1982);
16. (b) E. Buncel, H. Wilson, and C. Chuagui. J. Am. Chem. Soc. 104, 4896 (1982);
17. (c) A.R. Fersht and Y. Requena. J. Am. Chem. Soc. 93, 6592 (1971).
18. (a) J.E. Dixon and T.C. Bruice. J. Am. Chem. Soc. 93, 3248 (1971);
19. (b) J. Gerstein and W.P. Jencks. J. Am. Chem. Soc. 86, 4655 (1964).
20. (a) C.H. DePuy, E.W. Della, J. Filley, J.J. Garbowski, and V.M. Bierbaum. J. Am. Chem. Soc. 105, 2481 (1983);
21. (b) S. Wolfe, D.J. Mitchell, H.B. Schlegel, C. Minot, and O. Eisenstein. Tetrahedron Lett. 23, 615 (1982).
22. E. Buncel and I.H. Um. J. Chem. Soc. Chem. Commun. 595 (1986).
23. R.M. Tarkka and E. Buncel. J. Am. Chem. Soc. 117, 1503 (1995).
24. (a) I.H. Um, H.W. Yoon, J.S. Lee, H.J. Moon, and D.S. Kwon. J. Org. Chem. 62, 5939 (1997);
25. (b) I.H. Um, G.J. Hahn, G.J. Lee, and D.S. Kwon. Bull. Korean Chem. Soc. 13, 642 (1992);
26. (c) D.S. Kwon, G.J. Lee, and I.H. Um. Bull. Korean Chem. Soc. 10, 642 (1989).
27. (a) W.P. Jencks and M. Gilchrist. J. Am. Chem. Soc. 88, 104 (1966);
28. (b) J. Am. Chem. Soc. 90, 2622 (1968);
29. (c) D.J. Palling and W.P. Jencks. J. Am. Chem. Soc. 106, 4869 (1984).
30. (a) E.A. Castro, M.I. Pizarro, and J.G. Santos. J. Org. Chem. 61, 5982 (1996);
31. (b) E.A. Castro, M. Cubillos, and J.G. Santos. J. Org. Chem. 62, 4395 (1997);
32. (c) E.A. Castro, J.G. Santos, J. Tellez, and M. Umana. J. Org. Chem. 62, 6568 (1997).
33. (a) I.H. Um, H.J. Kwon, D.S. Kwon, and J.Y. Park. J. Chem. Res. Synop. 301, J. Chem. Res. Miniprint, 1801 (1995);
34. (b) I.H. Um, M.J. Kim, J.S. Min, and D.S. Kwon. Bull. Korean Chem. Soc. 18, 523 (1997);
35. (c) I.H. Um, E.S. Yeom, and D.S. Kwon. Bull. Korean Chem. Soc. 18, 865 (1997).
36. (a) C.D. Johnson. Tetrahedron, 36, 3461 (1980);
37. (b) A. Pross. Isr. J. Chem. 26, 390 (1985).
38. (a) I. Lee, C.S. Shim, S.Y. Chung, H.Y. Kim, and H.W. Lee. J. Chem. Soc. Perkin Trans. 2, 1919 (1988);
39. (b) K.H. Yew, H.J. Koh, H.W. Lee, and I. Lee. J. Chem. Soc. Perkin Trans. 2, 2263 (1995).
40. I.H. Um, J.S. Jeon, and D.S. Kwon. Bull. Korean Chem. Soc. 12, 406 (1991).
41. N.B. Chapman and J. Shorter (Editors). Advances in linear free energy relationships. Plenum, London, 1972.
42. D. Stefanidis, S. Cho, S. Dhe-Paganon. and W.P. Jencks. J. Am. Chem. Soc. 115, 1650 (1993).
43. R.A.Y. Jones. Physical and mechanistic organic chemistry. 2nd ed. 1984. pp. 38-67.
44. J.F. Kirsch, W. Chewell, and A. Simon. J. Org. Chem. 33, 127 (1968).
45. I.H. Um, Y.J. Hong, and D.S. Kwon. Tetrahedron, 53, 5073 (1997).
46. I.H. Um, E.K. Chung, and D.S. Kwon. Tetrahedron Lett. 38, 4787 (1997).
47. H.C. Brown and Y. Okamoto. J. Am. Chem. Soc. 80, 4979 (1958).
48. G. Alberghina and S. Fisichella. J. Chem. Soc. Perkin Trans. 2, 81 (1978).
49. E.K. Chung. M.S. thesis. Ewha Womans University, Seoul, Korea. 1997.
50. (a) G. Moutiers, E. Le Guevel, L. Villien, and F. Terrier. J. Chem. Soc. Perkin Trans. 2, 7 (1997);
51. (b) J.D. Aubort, R.F. Hudson, and R.C. Woodcock. Teterahedron Lett. 24, 2229 (1973).
52. (a) I.H. Um, S.J. Oh, and D.S. Kwon. Tetrahedron Lett. 36, 6903 (1995);
53. (b) R.A. Moss, S. Swarup, and S. Ganguri. J. Chem. Soc. Chem. Commun. 860 (1987);
54. (c) R. Curci and F. Di Furia. Int. J. Chem. Kinet. 7, 341 (1975).
55. E. Buncel, H. Wilson, and C. Chuagui. J. Am. Chem. Soc. 104, 4896 (1982).
56. J.E. Dixon and T.C. Bruice. J. Am. Chem. Soc. 94, 2052 (1972).
57. E. Buncel and S. Hoz. Tetrahedron Lett. 24, 4777 (1983).
58. I.H. Um, G.J.Lee, and D.S. Kwon. Bull. Korean Chem. Soc. 11, 262 (1990).
59. W.P. Jencks and F. Regenstein. In Handbook of biochemistry. Selected data for molecular biology. Edited by H.A. Sober. The Chemical Rubber Co., Cleveland, Ohio. 1968.
60. (a) J.F. Kirsch and C.D. Hubbard, Biochem. 13, 2483 (1972).
61. (b) A.A. Humffray and J.J. Ryan. J. Chem. Soc. (B). 468 (1967).
62. (c) A.R. Katritsky, R.T. Langthorne, H.A. Muathin, and R.C. Patel. J. Chem. Soc. Perkin Trans. 1, 2601 (1983).
63. E. Buncel, I.H. Um, and S. Hoz. J. Am. Chem. Soc. 111, 971 (1989).