Abstract
The inclusion complexation ofβ-CD with 1-substituted naphthalenes has been investigated by fluorescence spectroscopy. It was observed that the association constants were influenced by the molar refraction (R m), hydrophobic constant (π x ), and Hammett constant (σ x ) of substituents in the guest compounds. The thermodynamic parameters ΔG0, ΔH 0, and ΔS 0 determined by measuring the temperature-dependentK a values shows that inclusion complex formation is enthalpy driven. The results are discussed in terms of enthalpy-entropy compensation.
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References
M.L. Bender and M.K. Miyama:Cyclodextrin Chemistry, Springer-Verlag, Berlin (1978).
I. Tabushi: in J.L. Atwood, J.E.D. Davies, and D.D. MacNicol (eds.),Inclusion Compounds, Academic Press, London, Vol. 3, Ch. 13 (1984).
R. Breslow: in J.L. Atwood, J.E.D. Davies, and D.D. MacNicol (eds.),Inclusion Compounds, Academic Press, London, Vol. 3, Ch. 14 (1984).
J. Szejtli:Cyclodextrin Technology, Kluwer, Dordrecht (1988).
S. Hamai:Bull. Chem. Soc. Jpn. 55, 2721 (1982).
M. Fujiki, H. Deguchi, and I. Sanemasa:Bull. Chem. Soc. Jpn. 61, 1163 (1988).
K. Harata and H. Ueddaira:Bull. Chem. Soc. Jpn. 42, 375 (1975).
Y. Inoue, T. Hakushi, Y. Liu, L.-H. Tong, B.-J. Shen, and D.-S. Jing:J. Am. Chem. Soc. 114, 475 (1993).
H.A. Benesi and J.H. Hildebrand:J. Am. Chem. Soc. 71, 2703 (1949).
C. Hansch and A. Leo:Substituent Constants for Correlation Analysis in Chemistry and Biology, Wiley, New York (1979).
D.M. Davies and J.R. Savage:J. Chem. Res. (S) 94 (1993).
G. Nemethy:Angew. Chem. Int. Ed. Engl. 6, 195 (1967).
J.T. Chou and P.C. Jurs:J. Chem. Inf. Comput. Sci. 19, 172 (1979).
C. Hansch and T. Fijita:J. Am. Chem. Soc. 86, 1616 (1964).
A. Leo, C. Hansch, and D. Elkins:Chem. Rev. 71, 525 (1971).
Y. Inoue and T. Hakushi:J. Chem. Soc., Perkin Trans. 2 935 (1985).
Y. Inoue, T. Hakushi, Y. Liu, L.-H. Tong, J. Hu, G.-D. Zhao, S. Huang, and B.-Z. Tian:J. Phys. Chem. 92, 2371 (1988).
Y. Liu, L.-H. Tong, Y. Inoue, and T. Hakushi:J. Chem. Soc., Perkin Trans. 2 1247 (1990).
Y. Liu, L.H. Tong, S. Huang, B.-Z. Tian, Y. Inoue, and T. Hakushi:J. Phys. Chem. 94, 2666 (1990).
B. Zhang and R. Breslow:J. Am. Chem. Soc. 115, 9353 (1993).
Y. Inoue, Y. Liu, L.-H. Tong, B.-J. Shen, and D.-S. Jin:J Am. Chem. Soc. 115, 10637 (1993).
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Guo, QX., Zheng, XQ., Ruan, XQ. et al. Substituent effect and enthalpy-entropy compensation on the inclusion ofβ-cyclodextrin with 1-substituted naphthalenes. J Incl Phenom Macrocycl Chem 26, 175–183 (1996). https://doi.org/10.1007/BF01053536
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DOI: https://doi.org/10.1007/BF01053536