Abstract
Complexation of various kinds of bisphenols (BPs) with cycloheptaamylose(β-cyclodextrin, β-CD) derivatives (β-CD, hydroxyethyl-β-CD (HE-β-CD), 2,6-di-O-methyl-β-CD (DM-β-CD) and polymerised β-CD (L-Poly-β-CD)) was examined fluorimetrically using2-anilinonaphthalene-6-sulfonic acid (2,6-ANS) as a probe. From the inhibitory effectof BPs on the inclusion of 2,6-ANS by the β-CD derivatives, the associationconstants (Kass) of BPs with the β-CD derivatives were determined.The Kass values for bisphenol B (BPB) with β-cyclodextrin derivatives except for L-Poly-β-CD were always larger than those for other BPs including bisphenol A (BPA), due to the interaction between the non-polar cavity and hydrophobic BPB. Thermodynamic parameters indicated that the entropy change was always largely negative (-90∼ -120 J/mol...K in the β-CD system, for example), and the inclusion of bisphenols into the CD cavity was completely enthalpy-driven. The very largely negative entropy change might be mainly due to the tight fixation of guest molecules in the CD cavity, resulting in the loss of freedom of both CD and guest molecules. The effect of the structure of guest and host molecules on the association was also examined.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
E.C. Dodds and W. Lawson: Proc. Roy. Soc. Lon. B. 125, 222 (1938).
J.E. Biles, T.P. McNeal, and T.H. Begley: J. Agr. Food Chem. 45, 4697 (1997).
R. Pulgar, M.F. Olea-Serrano, A. Novillo-Fertrell, A. Rivas, P. Pazos, V. Pedraza, J.-M. Navajas, and N. Olea: Environ. Health Perspect. 108, 21 (2000).
Y. Maeda, T. Fukuda, H. Yamamoto, and H. Kitano: Langmuir 13, 4187 (1997).
H. Kitano, Y. Taira, and H. Yamamoto: Anal. Chem. 72, 2976 (2000).
M. Fukuda, Doctor Thesis, Kyoto University (1985).
G.C. Catena and F. B. Bright: Anal. Chem. 61, 905 (1989).
T. Hirasawa, Y. Maeda, and H. Kitano: Macromolecules 31, 4480 (1998).
P. Collins and R. Ferrier: Monosaccharides, John Wiley & Sons, Chichester (1995).
H. Kitano and Y. Taira: Langmuir 18, 5835 (2002).
S. Murai, S. Imajo, Y. Takasu, K. Takahashi, and K. Hattori: Environ. Sci. Technol. 32, 782 (1998).
M.V. Rekharsky, F.P. Schwarz, Y.B. Tewari, and R.N. Goldberg: J. Phys. Chem. 98, 10282 (1994).
Y. Inoue, T. Hakushi, Y. Liu, L.-H. Tong, B.-J. Shen, and D.-S. Jin: J. Am. Chem. Soc. 115, 475 (1993).
W. Linert, L. Han, and I. Lukovits: Chem. Phys. 139, 441 (1989).
R.I. Gelb and J.S. Alper: J. Phys. Org. Chem. 8, 825 (1995).
M.V. Rekharsky, F.P. Schwarz, Y.B. Tewari, R.N. Goldberg, M. Tanaka, and Y. Yamashoji: J. Phys. Chem. 98, 4098 (1994).
M. Komiyama and M.L. Bender: J. Am. Chem. Soc. 100, 2259 (1978).
E.A. Lewis and L.D. Hansen: J. Chem. Soc. Perkin Trans II 2081 (1973).
K. Ikeda, K. Uekama, and M. Otagiri: Chem. Phar. Bull. 23, 201 (1975).
L.-H. Tong and Y. Liu, Youji Huxaue: Org. Chem. 10, 342 (1990).
H.-J. Schneider and A. Yatsimirsky: Principles and Methods in Supramolecular Chemistry, John Wiley & Sons, Chichester (2000).
W.P. Jencks: Catalysis in Chemistry and Enzymology, McGraw-Hill, New York, 427 (1969).
R.H. Wood and P.T. Thompson: Proc. Natl. Acad. Sci. USA 87, 946 (1990)
A. Bondi: J. Phys. Chem. 68, 441 (1964).
W. Kauzmann: Adv. Protein Chem. 14, 1 (1959).
S. Kunugi: Kagaku 42, 200 (1987).
W.J. LeNoble, S. Srivastava, R. Breslow, and G. Trainor: J. Am. Chem. Soc. 105, 2745 (1983).
S. Makimoto, K. Suzuki, and Y. Taniguchi: J. Phys. Chem. 86, 4544 (1982).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kitano, H., Endo, H., Gemmei-Ide, M. et al. Inclusion of Bisphenols by Cyclodextrin Derivatives. Journal of Inclusion Phenomena 47, 83–90 (2003). https://doi.org/10.1023/B:JIPH.0000003879.99301.cd
Issue Date:
DOI: https://doi.org/10.1023/B:JIPH.0000003879.99301.cd