Changing mechanisms in the β-cyclodextrin-mediated hydrolysis of phenyl esters of perfluoroalkanoic acids

Journal of Organic Chemistry

Volumn 68, Issue 18, 2003, Pages 6887-6893

  Fernández, Mariana A ^a   De Rossi, Rita H ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

REACTION RATES;

HYDROLYSIS; NEGATIVE IONS; PHASE TRANSITIONS;

ESTERS;

ALKANOIC ACID; BETA CYCLODEXTRIN; CARBONYL DERIVATIVE; ESTER; MONOMER; PHENYL ESTER; PHENYL HEPTAFLUOROBUTANOATE; PHENYL PENTAFLUOROPROPANOATE; PHENYL PERFLUOROOCTANOATE; PHENYL TRIFLUOROACETATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; EQUILIBRIUM CONSTANT; FLUORINATION; HYDROLYSIS; IONIZATION; REACTION ANALYSIS;

ALGORITHMS; CYCLODEXTRINS; ESTERS; FLUOROCARBONS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; MASS SPECTROMETRY; SOLUTIONS; SOLVENTS; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 0042839570     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034402b     Document Type: Article

References (39)

1. Breslow, R.; Trainor, G.; Ueno, A. J. Am. Chem. Soc. 1983, 105, 2739.
2. Van Etten, R. L.; Sebastian, J. F.; Clowes, G. A.; Bender, M. L. J. Am. Chem. Soc. 1967, 89, 3242.
3. Tee, O. S.; Takasaki, B. K. Can. J. Chem. 1985, 63, 3540.
4. Tee, O. S.; Mazza, C.; Du, X.-X. J. Org. Chem. 1990, 55, 3603.
5. Menger, F. M.; Ladika, M. J. Am. Chem. Soc. 1987, 109, 3145.
6. Komiyama, M.; Bender, M. L. J. Am. Chem. Soc. 1978, 100, 4576.
7. Granados, A.; de Rossi, R. H. J. Org. Chem. 1993, 58, 1771.
8. Barthelemy, P.; Tomao, V.; Selb, J.; Chaudier, Y.; Pucci, B. Langmuir 2002, 18, 2557.
9. Eastoe, J.; Paul, A.; Downer, A. Langmuir 2002, 18, 3014.
10. Fernández, M. A.; de Rossi, R. H. J. Org. Chem. 1997, 62, 7554.
11. Fernández, M. A.; de Rossi, R. H.; Cervelló, E.; Jaime, C. J. Org. Chem. 2001, 66, 4399.
12. Tee, O. S.; Du, X.-X. J. Am. Chem. Soc. 1992, 114, 620.
13. Shinoda, K.; Hato, M.; Hayashi, T. J. Phys. Chem. 1972, 76, 909.
14. Lindström, U. M. Chem. Rev. 2002, 102, 2751.
15. Bernasconi, C. F. Relaxation Kinetics; Academic Press: New York, 1976; p 142.
16. It should be noticed that at pH 6.00, the reactions were measured in a conventional spectrophotometer in 5 cm path cells, whereas at pH 9, the measurements were carried out in a stopped flow apparatus where the optical pathlength is only 1 cm.
17. Wilson, L. D.; Verral, R. E. J. Phys. Chem. B 1998, 102, 480.
18. (a) Jiang, X.-K.; Hui, Y.-Z.; Fan, W.-Q. J. Am. Chem. Soc. 1984, 106, 3839.
19. (b) Jiang, X.-K. Acc. Chem. Res. 1988, 21, 362.
20. Granados, A.; de Rossi, R. H. J. Am. Chem. Soc. 1995, 117, 3690.
21. Tee, O. S. Adv. Phys. Org. Chem. 1994, 29, 1.
22. Komiyama, M.; Inoue, S. Bull. Chem. Soc. Jpn. 1980, 53, 3334.
23. Griffiths, D. W.; Bender, M. L. J. Am. Chem. Soc. 1973, 95, 1679.
24. Lach, J. L.; Chin, T. F. J. Pharm. Sci. 1964, 53, 924.
25. Chin, T. F.; Chung, P. H.; Lach, J. L. J. Pharm. Sci. 1968, 57, 44.
26. De Lisi, R.; Milioto, S.; De Giacomo, A.; Inglese, A. Langmuir 1999, 15, 5014.
27. Bonora, G. M.; Fornasier, R.; Scrimin, P.; Tonellato, U. J. Chem. Soc., Perkin Trans 2 1995, 367.
28. Tee, O. S. Carbohydr. Res. 1989, 192, 181.
29. Kurz, J. L. J. Am. Chem. Soc. 1963, 85, 987.
30. The difference in steric energy for the complex with the aryl ring inside and that with the trifluoromethyl inside was calculated as 4.2 kcal/mol (see ref 11).
31. The reaction of m-nitro phenyl acetate is more strongly accelerated than that of the para-substituded derivative due to the more favorable orientation of the substrate in the complex (see ref 20).
32. (a) Hartwell, E.; Hodgson, D. R. W.; Kirby, A. J. J. Am. Chem. Soc. 2001, 122, 9326.
33. (b) Menger, F. M. Acc. Chem. Res. 1985, 18, 128.
34. Bernasconi, C. F. Relaxation Kinetics; Academic Press: New York, 1976; Chapter 9.
35. Fernández, M. A.; Granados, A. M.; El Seoud O. A.; de Rossi; R. H. Langmuir 2002, 18, 8786.
36. Adenier, A.; Aubard, J.; Schwaller, M.-A J. Phys. Chem. 1992, 96, 8785.
37. Analytical Chemistry. The Working Tools; Strouts, C. R. N., Gilgilan, J. H., Wilson, H. N., Eds.; Oxford University Press: London, 1958, pp 228-233.
38. Cyclodextrins were a gift from the pharmaceutical company Ferromet S. A., Buenos Aires, Argentina.
39. Clark, R. F.; Simons, J. H. J. Am. Chem. Soc. 1953, 75, 6305.