Mechanism of phthalate ester hydrolysis in water and in cyclodextrinmediated reactions

Arkivoc

Volumn 2003, Issue 10, 2003, Pages 127-138

  Andrés, Gabriel O ^a   De Rossi, Rita H ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

Cyclodextrin; Ester hydrolysis mechanism; Intramolecular catalysis

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; 2 PROPANOL; BENZYL HYDROGEN PHTHALATE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXANOL; HYDROXYL GROUP; PHTHALIC ACID ESTER; PROPANOL; SODIUM HYDROXIDE; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; HYDROGEN BOND; HYDROLYSIS; PH; TEMPERATURE;

EID: 3242730280     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. a) Kirby, A.J.; P. W. Lancaster, P.W. J. Chem. Soc. Perkin 2, 1972, 1206.
2. b) J. Suh, J.; Chun, K.H. J. Am. Chem. Soc., 1986, 108, 305.
3. c) Menger, F. M.; Ladika, M. J. Am. Chem. Soc., 1988, 110, 6794.
4. Aldersley, M. F.; Kirby, A. J.; Lancaster, P. W. J. Chem. Soc., Perkin 2, 1974, 1504.
5. a) Bender, M. L.; M. Komiyama, M. Cyclodextrin Chemistry. Springer-Verlag, New York. 1977.
6. b) I. Tabushi, I.; Kuroda, Y. in Advances in Catalysis Vol. 32 Edited by D. D. Eley, H. Pines, P. B. Weisz, Academic Press, London. 1983. pp 417-462.
7. a) Takashi, K. Chem. Rev., 1998, 98, 2013.
8. b) Breslow; Dong, S.D. Chem. Rev., 1998, 98, 1997.
9. c) L. Viola and R. H. de Rossi, Can. J. Chem., 1999, 77, 860.
10. a) Hartwell, E.; Hodgson, D. R. W.; Kirby, A. J. J. Am. Chem. Soc., 2001, 122, 9326.
11. b) Menger, F. M. Acc. Chem. Res., 1985, 18, 128.
12. a) Kim, Y.; Yoon, M.; Kim, D.J. Photochem Photobiol A Chem. 2001, 138, 167.
13. b) Vizvardi, K.; Desmet, K.; Luyten, I.; Sandra, P.; Hoornaert, G. Vander Eycken, E. Org. Lett. 2001, 3, 1173.
14. Andrés, G. O.; Granados, A. M.; de Rossi, R. H. J. Org. Chem., 2001, 66, 7653.
15. Castro, E. A. Chem. Rev. 1999, 99, 3505
16. 2 (10.62). The value reported for benzyl alcohol is 15.2 (Menger, F. M.; Ladika, M. J. Amer. Chem. Soc., 1987, 109, 3145) which seems too high
17. 2 (10.62). The value reported for benzyl alcohol is 15.2 (Menger, F. M.; Ladika, M. J. Amer. Chem. Soc., 1987, 109, 3145) which seems too high
18. Kirsch, J. F.; Jencks, W.P J. Am. Chem. Soc. 1964, 86, 837
19. Ba-Saif, S.; Luthra, A. K.; Williams, A. J. Am. Chem. Soc. 1989, 111, 2647.
20. Guthrie, J. P.; J. Am. Chem. Soc. 1991, 113, 3941.
21. Stefanidis, D.; Cho, S.; Dhe-Pagamon, S.; Jencks, W. P. J. Am. Chem. Soc 1993, 115, 1650.
22. Hengge, A. C.; Hess, R. A. J. Am. Chem. Soc. 1994, 116, 11256.
23. Takahashi, K. Chem. Rev. 1998, 98, 2013.
24. Tee, O. S.; Bozzi, M.; Hoeven, J. J.; Gadosy, T. A. J. Am. Chem. Soc. 1993, 115, 8990
25. This is pKa of β-cyclodextrin reported by Hamai, S. Bull. Chem Soc. Jpn 1996, 69, 543., but the pKa of HPCD is not expected to be very different from this value
26. Sigmaplot 5.0 was used for non-linear fitting and the parameters were a, b, and c or we used the experimentally determined value of a and calculated b and c. Both methods gave similar results
27. Menger, F. M.; Ladika, M. J. Amer. Chem. Soc., 1987, 109, 3145
28. Andrés, G.O.; Granados, A.M.; de Rossi, R. H. J. Chem. Soc. Perkin 2, 2002, 1502.
29. Perrin, D.D.; Armarego; W. L. G. Purification of Laboratory Chemicals, Butterworth-Heinemann Ltd, Great Britain, 3th Edition, 1994, p 68.
30. "Handbook of Chemistry and Physics" CRC Press, 72nd Edition, Lide D. R. Editor, 1991-1992, p 8-30 to 8-35.
31. Padwa, A.; Carter, S. P.; Nimmesgern, H.; Stull; P. D. J. Am. Chem. Soc. 1988, 110, 2894.