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Complex formation of hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin with substituted benzenes in aqueous solution

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Abstract

The complex formation of hexakis (2,3,6-tri-O-methyl)-α-cyclodextrin with substituted benzenes has been investigated by circular dichroism (CD) spectroscopy. The sign and shape of the CD spectra markedly differ from the spectra of corresponding α-cyclodextrin complexes because of the distorted conformation of the host molecule and/or the difference in the geometry of the host-guest interaction. Enthalpy and entropy changes of the complex formation are determined by using the CD band intensities measured at various temperatures and host concentrations. Negative values of ΔH and ΔS indicate that the hydrophobic interaction is not the major driving force for the complex formation. The guest molecule is suggested to be tightly bound within the host cavity through the induced-fit conformational change of the host molecule.

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References

  1. M. L. Bender and M. Komiyama,Cyclodextrin Chemistry, Springer-Verlag, Berlin (1978).

    Google Scholar 

  2. J. Szejtli,Cyclodextrins and their Inclusion Complexes, Akademiai Kiado, Budapest (1982).

    Google Scholar 

  3. W. L. Hinze,Separation and Purification Methods 10, 159–237 (1981).

    Google Scholar 

  4. A. P. Croft and R. A. Bartsch,Tetrahedron 39, 1417–1474 (1983).

    Google Scholar 

  5. K. Harata, K. Uekama, M. Otagiri, andF. Hirayama,Bull. Chem. Soc. Jpn. 55, 407–410 (1982).

    Google Scholar 

  6. K. Harata, K. Uekama, M. Otagiri, and F. Hirayama,Bull. Chem. Soc. Jpn. 56, 1732–1736 (1983).

    Google Scholar 

  7. K. Harata, K. Uekama, M. Otagiri, and F. Hirayama,J. Incl. Phenom. 1, 279–293 (1984).

    Google Scholar 

  8. B. Casu, M. Reggiani, and G. R. Sanderson,Carbohydr. Res. 76, 59–66 (1979).

    Google Scholar 

  9. Y. Inoue, Y. Takahashi, and R. Chujo,Carbohydr. Res. 144, C9-C11 (1985).

    Google Scholar 

  10. B. Casu, M. Reggiani, G. G. Gallo, and A. Vigevani,Tetrahedron 24, 803–821 (1968).

    Google Scholar 

  11. K. Harata,Bull. Chem. Soc. Jpn. 52, 1807–1812 (1981).

    Google Scholar 

  12. K. Harata,Bioorg. Chem. 10, 255–265 (1981).

    Google Scholar 

  13. K. Harata and H. Uedaira,Bull. Chem. Soc. Jpn. 48, 375–378 (1975).

    Google Scholar 

  14. J. Tanaka,Bull. Chem. Soc. Jpn. 36, 833–847 (1963).

    Google Scholar 

  15. K. Harata,Chem. Lett. 1986, 2057–2060.

  16. K. Harata, K. Uekama, M. Otagiri, and F. Hirayama,Bull. Chem. Soc. Jpn. 55, 3904–3910 (1982).

    Google Scholar 

  17. K. Harata,Bull. Chem. Soc. Jpn. 50, 1416–1424 (1977).

    Google Scholar 

  18. K. Harata, K. Uekama, M. Otagiri, and F. Hirayama,Bull. Chem. Soc. Jpn. 60, 497–502 (1987).

    Google Scholar 

  19. E. A. Lewis and L. D. Hansen,J. Chem. Soc., Perkin Trans. 2, 1973, 2081–2085.

    Google Scholar 

  20. K. Uekama, F. Hirayama, K. Esaki, and M. Inoue,Chem. Pharm. Bull. 27, 76–79 (1979).

    Google Scholar 

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Harata, K., Tsuda, K., Uekama, K. et al. Complex formation of hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin with substituted benzenes in aqueous solution. Journal of Inclusion Phenomena 6, 135–142 (1988). https://doi.org/10.1007/BF00663046

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  • DOI: https://doi.org/10.1007/BF00663046

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