Hydrolysis of aryl hydrogen maleate esters mediated by cyclodextrins - Effect on the intramolecular catalysis

Canadian Journal of Chemistry

Volumn 83, Issue 9, 2005, Pages 1281-1286

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

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

Cyclodextrins; Hydrolysis; Inhibition; Intramolecular catalysis

Indexed keywords

CATALYSIS; CORRELATION THEORY; ESTERS; HYDROGEN; REACTION KINETICS; SUBSTRATES;

CYCLODEXTRINS; INHIBITION; INTRAMOLECULAR CATALYSIS;

HYDROLYSIS;

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ANION; CARBOXYLIC ACID; ESTER DERIVATIVE; HYDROGEN; HYDROGEN MALEATE ESTER; MALEIC ANHYDRIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; EQUILIBRIUM CONSTANT; GEOMETRY; HYDROLYSIS; INFRARED SPECTROSCOPY; PKA; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 33644597002     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-144     Document Type: Article

References (35)

1. A.J. Kirby and P.W. Lancaster. J. Chem. Soc. Perkin Trans. 2, 1206 (1972).
2. J. Suh and K.H. Chun. J. Am. Chem. Soc. 108, 305 (1986).
3. F.M. Menger and M. Ladika. J. Am. Chem. Soc. 110, 6794 (1988).
4. A.D. Bond, A.J. Kirby, and E. Rodriguez. Chem. Commun. 2266 (2001).
5. M.L. Bender and M. Komiyama. Cyclodextrin chemistry. Springer-Verlag, New York. 1978.
6. K. Takashi. Chem. Rev. 98, 2013 (1998).
7. R. Breslow and S.D. Dong. Chem. Rev. 98, 1997 (1998).
8. E.M.M. Del Valle. Proc. Biochem. 39, 1033 (2004).
9. A.R. Hedges. Chem. Rev. 98, 2035 (1998).
10. O.S. Tee and B.K. Takasaki. Can. J. Chem. 63, 3540 (1985).
11. O.S. Tee, M. Bozzi, J.J. Hoeven, and T.A. Gadosy. J. Am. Chem. Soc. 115, 8990 (1993).
12. M.A. Fernandez and R.H. de Rossi. J. Org. Chem. 62, 7554 (1997).
13. L. Viola and R.H. de Rossi. Can. J. Chem. 77, 860 (1999).
14. T.A. Gadosy, M.J. Boyd, and O.S. Tee. J. Org. Chem. 65, 6879 (2000).
15. V.T. D'Souza and M.L. Bender. Ace. Chem. Res. 20, 146 (1987).
16. A. Craft and R.A. Bartsch. Tetrahedron, 39, 1407 (1983).
17. A.R. Khan, P. Forga, K.J. Stine, and V.T. D'Souza. Chem. Rev. 98, 1977 (1998).
18. D.D. Sternbach and D.M. Bossana. J. Am. Chem. Soc. 104. 5853 (1982).
19. A.M. Granados and R.H. de Rossi. J. Org. Chem. 66, 1548 (2001).
20. G.O. Andrés, A.M. Granados, and R.H. de Rossi. J. Chem. Soc. Perkin Trans. 2, 1502 (2002).
21. G.O. Andrés and R.H. de Rossi. ARKIVOC, 10, 127 (2003).
22. A.J. Kirby. Adv. Org. Chem. 17, 183 (1980).
23. G.O. Andres and R.H. de Rossi. J. Org. Chem. 70, 1445 (2005).
24. J. Kurz. J. Am. Chem. Soc. 65, 987 (1963).
25. O.S. Tee. Carbohydr. Res. 192, 181 (1989).
26. O.S. Tee, C. Mazza, and X.-X. Du. J. Org. Chem. 55, 3603 (1990).
27. O.S. Tee and X.-X. Du. J. Am. Chem. Soc. 114, 620 (1992).
28. H. Hirai, Y. Shiraishi, H. Mihori, K. Saito, and T. Kawamura. Polym. J. 28, 91 (1996).
29. A. Kokkinou, K. Yannakopoulou, I.M. Mavridis, and D. Mentzafos. Carbohydr. Res. 332, 85 (2001).
30. E. Hartwell, D.R.W. Hodgson, and A.J. Kirby. J. Am. Chem. Soc. 122, 9326 (2001).
31. F.M. Menger. Acc. Chem. Res. 18, 128 (1985).
32. D.W. Griffiths and M.L. Bender. J. Am. Chem. Soc. 95, 1679 (1973).
33. D.D. Perrin and W.L.G. Armarego. Purification of laboratory chemicals. 3rd ed. Butterworths-Heinemann Ltd, Oxford, UK. 1994.
34. I. Bojanowska and T. Jasinski. Pol. J. Chem. 63, 455 (1989).
35. D.R. Lide (Editor). Handbook of chemistry and physics. 72nd ed. CRC Press, Boca Raton, Fla. pp. 8-30-8-35. 1991 to 1992.