Kinetics and mechanism of phosphate-catalyzed hydrolysis of benzoate esters: Comparison with nucleophilic catalysis by imidazole and o-iodosobenzoate

Journal of the Chemical Society. Perkin Transactions 2

Volumn 2, Issue 6, 2002, Pages 1053-1058

  El Seoud, Omar A ^a   Ruasse, Marie Françoise ^b   Rodrigues, Wagner A ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; ENTROPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; PHOSPHATES; RATE CONSTANTS; SOLVENTS; SPECTROPHOTOMETRY; SYNTHESIS (CHEMICAL);

NUCLEOPHILIC CATALYSIS;

ESTERS;

EID: 0035999946     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b202728n     Document Type: Article

References (29)

1. M. L. Bender, R. J. Bergeron and M. Komiyama The Bioorganic Chemistry of Enzyme Catalysis, Plenum, New York, 1984, pp. 45, 130.
2. W. P. Jencks Catalysis in Chemistry and Enzymology, Dover, New York, 1987, pp. 42, 163, 463.
3. N. S. Isaacs Physical Organic Chemistry, Longman, Essex, 1987 375.
4. P. Menegheli, J. P. S. Farah, O. A. El Seoud Ber. Bunsenges. Phys. Chem. 1991 95 1610.
5. O. A. El Seoud, M. F. Martins J. Phys. Org. Chem. 1995 8 637.
6. T. H. Fife Acc. Chem. Res. 1993 26 325.
7. D. D. Perrin, W. L. F. Armarego and D. R. Perrin Purification of Laboratory Chemicals, 2nd edn, Wiley-Interscience, New York, 1988.
8. V. A. Izmail’skii, A. V. Belotsvetov J. Gen. Chem. USSR. 1941 11 650 Chem. Abstr. 1942 36 436.
9. R. C. Brown, R. E. Kremers J. Am. Pharm. Assoc. 1922 11 607.
10. E. de B. Barnett, I. G. Nixon Chem. News 1924 129 190.
11. W. P. Jencks, J. Carriuolo J. Am. Chem. Soc. 1961 83 1743.
12. W. P. Jencks, G. Di Sabato J. Am. Chem. Soc. 1961 83 4393, 4400.
13. G. Camici, G. Manao, G. Cappugi, G. Ramponi Experientia 1976 32 535.
14. C. D. Hubbard, J. F. Kirsch Biochemistry 1972 11 2483.
15. E. A. Castro, G. B. Steinfort J. Chem. Soc., Perkin Trans. 2 1983 453.
16. R. A. Moss, S. Swarp, S. Ganguli J. Chem. Soc., Chem. Commun. 1987 860.
17. A. Williams Acc. Chem. Res. 1989 22 387.
18. S. Ba-Saif, A. K. Luthra, A. J. Williams J. Am. Chem. Soc. 1987 109 6362.
19. E. Buncel, H. I. Um, S. S. Hoz J. Am. Chem. Soc. 1989 111 971.
20. Preliminary (unpublished) results have shown that the hydrolysis of 4-nitrobenzoyl phosphate in water in the presence of 0.1 M phosphate buffer, at pH = 7.8, at 39 °C has a half-life of 28 minutes, compared with 3.04 minutes for the hydrolysis of I-d under more or less similar experimental conditions. Both reactions should be slowed down in 65% acetonitrile in water.
21. C. J. O’Connor, R. G. Wallace Aust. J. Chem. 1984 37 2559.
22. D. Herschlag, W. P. Jencks J. Am. Chem. Soc. 1989 111 7587.
23. A. Kanavarioti, M. T. Rosenbach J. Org. Chem. 1991 56 1513.
24. I. M. Kovach, A. J. Bennet, J. A. Bibbs, Q. Zhao J. Am. Chem. Soc. 1993 115 5138.
25. V. G. Machado, C. A. Bunton, C. Zucco, F. Nome J. Chem. Soc., Perkin Trans. 2 2000 169.
26. J. Shorter Pure Appl. Chem. 1994 66 2451.
27. O. A. El Seoud, P. Menegheli, P. A. R. Pires, N. Z. Kiyan J. Phys. Org. Chem. 1994 7 431.
28. J. E. Delbene, I. Cohen J. Am. Chem. Soc. 1978 100 5285.
29. D. W. Smith J. Chem. Educ. 1977 54 540.