Kinetic study of hydrolysis of benzoates. Part XXII. Variation of the ortho inductive, resonance and steric terms with temperature in the alkaline hydrolysis of substituted phenyl benzoates in aqueous 2.25 M Bu4NBr

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 3, 2000, Pages 583-594

  Nummert, Vilve ^a   Piirsalu, Mare ^a  

^a UNIVERSITY OF TARTU   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; CORRELATION METHODS; ELECTRON RESONANCE; HYDROLYSIS; ORGANIC SOLVENTS; RATE CONSTANTS; REACTION KINETICS; SPECTROPHOTOMETRY; SUBSTITUTION REACTIONS; TEMPERATURE; THERMAL EFFECTS; WATER;

ACIDIDC HYDROLYSIS; BENZOATES; PHENYL BENZOATES; SECOND ORDER RATE CONSTANTS; STERIC TERM FOR WATER; SUSCEPTIBILITY;

AROMATIC COMPOUNDS;

EID: 0034160966     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904741g     Document Type: Article

References (70)

1. V. Nummert, Org. React., 1989, 26, 98.
2. T. Fujita and T. Nishioka, Prog. Phys. Org. Chem., 1976, 12, 49.
3. M. Charton, Prog. Phys. Org. Chem., 1971, 8, 235.
4. M. Charton, J. Am. Chem. Soc., 1969, 91, 624.
5. L. P. Hammett, Physical Organic Chemistry, McGraw-Hill Book Co., New York, N.Y., 1940, p. 206.
6. R. W. Taft, Jr., Steric Effects in Organic Chemistry, ed. M. S. Newman, Wiley, New York, 1956, p. 556.
7. J. Shorter, Advances in Linear Free Energy Relationships, eds. N. B. Chapman and J. Shorter, Plenum Press, London, 1972, p. 71.
8. N. B. Chapman, J. Shorter and J. H. P. Utley, J. Chem. Soc. (B), 1963, 1291.
9. N. B. Chapman, M. G. Rodgers and J. Shorter, J. Chem. Soc. (B), 1968, 157.
10. A. C. Farthing and B. Nam, Steric Effects in Conjugate Systems, ed. G. W. Gray, Butterworth, London, 1958, p. 131.
11. K. Bowden and G. E. Manser, Can. J. Chem., 1968, 46, 2941.
12. M. Charton, J. Am. Chem. Soc., 1974, 97, 3691.
13. M. Charton, J. Am. Chem. Soc., 1977, 42, 3531.
14. M. Charton, J. Org. Chem., 1968, 33, 3872.
15. M. Charton, J. Am. Chem. Soc., 1969, 91, 619.
16. M. Charton, J. Am. Chem. Soc., 1969, 91, 6649.
17. M. Charton, J. Am. Chem. Soc., 1975, 97, 3691.
18. M. Hojo, M. Utaka and Z. Yoshida, Tetrahedron, 1971, 27, 5433.
19. S. C. Dash and G. B. Behera, J. Indian Chem. Soc., 1980, LVII, 542.
20. T. Fujita, Prog. Phys. Org. Chem., 1983, 14, 75.
21. P. Segura, J. Am. Chem. Soc., 1985, 50, 1045.
22. C. N. Robinson, J. L. Horton, D. O. Foshee, J. W. Jones, S. H. Hanissian and C. D. Slater, J. Org. Chem., 1986, 51, 3535.
23. E. Kutter and C. Hansch, J. Med. Chem., 1969, 12, 6.
24. C. G. Swain and E. C. Lupton, J. Am. Chem. Soc., 1968, 90, 4328.
25. L. A. Janovskaja and S. S. Juffit, Organic Synthesis In Two-Phase Systems, Moscow, Khimia, 1982 (in Russian).
26. I. A. Koppel, A. Prodel, J. B. Koppel and V. O. Pihl, Org. React., 1990, 27, 74.
27. J. Steigman and D. Sussman, J. Am. Chem. Soc., 1967, 89, 6406.
28. V. Nummert and A. Bogdanov, Org. React., 1989, 26, 231.
29. V. Nummert, M. Piirsalu and V. Palm, Org. React., 1996, 30, 85.
30. V. Nummert and M. Piirsalu, Org. React., 1975, 11, 899.
31. V. Nummert and M. Piirsalu, Org. React., 1975, 11, 921.
32. V. Nummert and M. Piirsalu, Org. React., 1995, 29, 109.
33. V. Nummert and M. Piirsalu, Org. React., 1996, 30, 95.
34. V. Nummert and M. Piirsalu, Org. React., 1997, 31, 101.
35. V. Nummert, M. Eek and M. Piirsalu, Org. React., 1981, 18, 363.
36. V. Nummert and V. Palm, Org. React., 1993, 28, 63.
37. V. Nummert and M. Eek, Org. React., 1984, 21, 304.
38. V. Nummert, M. Eek and V. Palm, Org. React., 1985, 22, 263.
39. V. Nummert, M. Piirsalu and V. Palm, Org. React., 1990, 27, 99.
40. V. Nummert and M. Piirsalu, Org. React., 1990, 27, 217.
41. V. Nummert, K. Ojassalu and A. Bogdanov, Org. React., 1989, 26, 92.
42. R. W. Taft, Jr and I. C. Lewis, J. Am. Chem. Soc., 1958, 80, 2436.
43. V. Nummert, M. Piirsalu and V. Palm, Org. React., 1993, 28, 82.
44. V. Nummert, Org. React., 1981, 28, 274.
45. V. Nummert and V. Palm, Org. React., 1980, 17, 292.
46. V. Nummert, R. Pärisma and M. Piirsalu, Org. React., 1986, 23, 83.
47. T. O. Püssa, V. M. Nummert and V. A. Palm, Reakts. Sposobn. Org. Soedin., 1972, 9, 697.
48. A. Uri, A. Tuulmets and V. Palm, Org. React., 1983, 29, 122.
49. V. Palm, J. Chem. Inf. Comput. Sci., 1990, 30, 409.
50. Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions, 5(II), ed. V. Palm, Publishing House of VINITI, Moscow, 1979.
51. R. W. Taft, Jr, S. Ehrenson, I. C. Lewis and R. E. Glick, J. Am. Chem. Soc., 1959, 81, 5352.
52. M. L. Bender, Mechanisms of Catalysis of Nucleophilic Reactions of Carboxylic Acid Derivatives, Chemical Reviews, 1960, vol. 60 (in Russian 1964).
53. J. F. Kirsch, W. Clewell and A. Simon, J. Org. Chem., 1968, 33, 127.
54. Z. S. Chaw, A. Fischer and D. A. R. Happer, J. Chem. Soc. (B), 1971, 1818.
55. T. Nishioka, T. Fujita, K. Kitamura and M. Nakajima, J. Org. Chem., 1975, 40, 2520.
56. V. R. Correia, I. M. Cuccovia and H. Chaimovich, J. Phys. Org. Chem., 1991, 4, 13.
57. I. A. Koppel and J. B. Koppel, Org. React., 1984, 21, 98.
58. Water. A Comprehensive Treatise, vol. 3, ed. F. Franks, Plenum Press, New York, London, 1973.
59. P. S. Jastremitski, G. V. Kokovina, A. K. Ljastsenko, O. J. Somoilov and J. A. Mirgorod, Zh. Fiz. Khim., 1979, 20, 612 (in Russian).
60. I. A. Koppel and J. B. Koppel, Org. React., 1983, 20, 513.
61. R. Bates, L. Johnson and R. A. Robinson, Chem. Anal. (Warsaw), 1972, 17, 479.
62. E. S. Amis, Solvent Effects on Reaction Rates and Mechanisms, Academic Press, New York, 1966.
63. E. Tommila and L. Palenius, Acta Chem. Scand., 1963, 17, 1980.
64. E. Tommila, Suom. Kemistil., B 1964, 37, 117.
65. M. Hojo, M. Utaka and Z. Yoshida, Tetrahedron Lett., 1966, 1, 25.
66. J. Steigman, D. Sussman, J. Am. Chem. Soc., 1967, 89, 6400.
67. J. E. Dersnoyers, G. E. Pelletier and C. Jolicoeur, Can. J. Chem., 1965, 43, 3233.
68. E. Tommila and A. Hella, Ann. Acad. Sci. Fenn., Chem., 1954, 53, 1954.
69. V. Nummert, Org. React., 1978, 15, 412.
70. N. B. Chapman, J. Shorter and J. H. P. Utley, J. Chem. Soc., 1963, 1291.