Binding of aliphatic ketones to cyclodextrins in aqueous solution

Journal of the Chemical Society. Perkin Transactions 2

Volumn 6, Issue , 1996, Pages 1243-1249

  Tee, Oswald S ^a   Fedortchenko, Alexei A ^a   Loncke, Paul G ^a   Gadosy, Timothy A ^a  

^a Gina Cody School of Engineering and Computer Science   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000240207     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/p29960001243     Document Type: Article

References (43)

1. (a) M. Bender and M. Komiyama, Cyclodextrin Chemistry, Springer-Verlag, New York, 1978;
2. (b) J. Szejtli, Cyclodextrins and their Inclusion Complexes, Akademiai Kiado, Budapest, 1982.
3. (a) J. Szejtli, Cyclodextrin Technology, Kluwer, Dordrecht, 1988;
4. (b) J. F. Stoddart and R. Zarzycki, Recl. Trav. Chim. Pays-Bas 1988, 107, 515;
5. (c) J. Szejtli, Carbohydr. Polym., 1990, 12, 375;
6. (d) G. Wenz, Angew. Chem., Int. Ed. Engl., 1994, 33, 803.
7. K. A. Connors, Binding Constants: The Measurement of Molecular Complex Stability, Wiley-Interscience, New York, 1987.
8. (a) H.-J. Schneider, Angew. Chem., Int. Ed. Engl., 1991, 30, 1417;
9. (b) H.-J. Schneider, Chem. Soc. Rev., 1994, 23, 227.
10. (a) O. S. Tee, Carbohydr. Res., 1989, 192, 181;
11. (b) O. S. Tee, Adv. Phys. Org. Chem., 1994, 29, 1.
12. (a) O. S. Tee and B. K. Takasaki, Can. J. Chem., 1985, 63, 3540;
13. (b) O. S. Tee and M. Bozzi, J. Am. Chem. Soc., 1990, 112, 7815;
14. (c) O. S. Tee, M. Bozzi, J. J. Hoeven and T. A. Gadosy, J. Am. Chem. Soc., 1993, 115, 8990;
15. (d) O. S. Tee, M. Bozzi, N. Clement and T. A. Gadosy, J. Org. Chem., 1995, 60, 3509.
16. (a) O. S. Tee, C. Mazza and X.-X. Du, J. Org. Chem., 1990, 55, 3603;
17. (b) O. S. Tee and X.-X. Du, J. Am. Chem. Soc., 1992, 114, 620;
18. (c) O. S. Tee, C. Mazza, R. Lozano-Hemmer and J. B. Giorgi, J. Org. Chem., 1994, 59, 7602.
19. (a) T. A. Gadosy and O. S. Tee, J. Chem. Soc., Perkin Trans. 2, 1994, 715;
20. T. A. Gadosy and O. S. Tee, J. Chem. Soc., Perkin Trans. 2, 1994, 2069;
21. (b) O. S. Tee and T. A. Gadosy, J. Chem. Soc., Perkin Trans. 2, 1994, 2191;
22. (c) O. S. Tee and T. A. Gadosy, J. Chem. Soc., Perkin Trans. 2, 1994, 2307;
23. (d) T. A. Gadosy and O. S. Tee, J. Chem. Soc., Perkin Trans. 2, 1995, 71;
24. (e) O. S. Tee and M. J. Boyd, J. Chem. Soc., Perkin Trans. 2, 1995, 1237.
25. (a) J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1988, 27, 89;
26. (b) H.-J. Schneider and H. Dürr, Frontiers in Supramolecular Organic Chemistry and Photochemistry VCH, Weinheim, 1990;
27. (c) F. Vögtle, Supramolecular Chemistry, Wiley, Chichester, 1991.
28. O. S. Tee, T. A. Gadosy and J. B. Giorgi, J. Chem. Soc., Perkin Trans. 2, 1993, 1705.
29. T. A. Gadosy, J. B. Giorgi and O. S. Tee, Can. J. Chem. 1996, in the press.
30. (a) Y. Matsui and K. Mochida, Bull. Chem. Soc. Jpn., 1979, 52, 2808;
31. (b) Y. Matsui, T. Nishioka and T. Fujita, Top. Curr. Chem., 1985, 128, 61;
32. (c) Cf. H. Fujiwara, H. Arakawa, S. Murata, and Y. Sasaki, Bull. Chem. Soc. Jpn., 1987, 60, 3891.
33. J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley, New York, 4th edn. 1992.
34. J. R. Keeffe and A. J. Kresge, The Chemistry of Enols, ed. Z. Rappoport, Wiley, New York, 1990, ch. 7.
35. H. Maskill, The Physical Basis of Organic Chemistry, Oxford University Press, Oxford, 1985, p. 341;
36. I. Eskendirov, B. Kabongo, L. Glasser and V. D. Sokolovskii, J. Chem. Soc., Faraday Trans., 1995, 91, 991.
37. (a) I. Satake, T. Ikenoue, T. Takashita, K. Hayakawa and T. Meda, Bull. Chem. Soc. Jpn., 1985, 58, 2746;
38. (b) I. Satake, S. Yoshida, K. Hayakawa, T. Meda and Y. Kusumoto, Bull. Chem. Soc. Jpn., 1986, 59, 3991;
39. (c) J. W. Park and H. J. Song, J. Phys. Chem., 1989, 93, 6454;
40. (d) I. Sanemasa, T. Osajima, and T. Deguchi, Bull. Chem. Soc. Jpn., 1990, 63, 2814.
41. (a) C. Tanford, The Hydrophobic Effect: Formation of Micelles and Biological Membranes, Wiley, New York, 2nd edn. 1980;
42. (b) M. H. Abraham, J. Am. Chem. Soc., 1982, 104, 2085.
43. W. Blokzijl and J. B. F. N. Engberts, Angew. Chem., Int. Ed. Engl., 1993, 32, 1545.