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The Effects of Cosolvents on the Complexation of α-Cyclodextrin with Alkylated Substances. Calorimetric Studies at 25 °C

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Abstract

The formation of complexes of α-cyclodextrin with 1,2-alkanediols, α,ω-alkanediols and some cycloalkanols has been studied calorimetrically at 25 °C in water, in 7 mol kg-1 aqueous urea and in 3 mol kg-1 aqueous glucose. When a complex is formed, calorimetry enables the calculation of both the enthalpy and the association constant, from which the free energy and the entropy of the process can be obtained. The forces involved in the association process are discussed in the light of the signs and values of the thermodynamic parameters obtained. The effect of the variation of the aqueous medium on the hydration of the interacting substances and the consequent changes in the association parameters have been investigated. As respect to water, complexes are less stable in urea and more stable in glucose. The analysis of the data shows that this is the result of a different enthalpy-entropy balance in the two solvent media. Deaquation of the interacting substances plays a major role in determining the stability of the inclusion complexes.

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REFERENCES

  1. A. Connors: Chem. Rev. 97, 1325 (1997).

    Google Scholar 

  2. W. Saenger: In J.L. Atwood, J. E. Davies, and D. MacNicol (eds.), Inclusion Compounds, Vol. 2, Academic Press, London, 1984, pp. 231–259.

    Google Scholar 

  3. W. Saenger: Angew. Chem. Int. Ed. Engl. 19, 344 (1980).

    Google Scholar 

  4. R.J. Clarke, J.H. Coates, and S.F. Lincoln: Adv. Carbohydr. Chem. Biochem. 46, 205 (1988 ).

    Google Scholar 

  5. O. Huber and J. Szejtli (eds.): Proceedings of the 4th International Symposium on Ciclodextrins, Kluwer Academic Publisher, Dordrecht (1988).

    Google Scholar 

  6. M.V. Rekharsky and Y. Inoue: Chem. Rev. 98, 1875 (1998).

    Google Scholar 

  7. P.C. Manor and W. Saenger: J. Am. Chem. Soc. 96, 3630 (1974).

    Google Scholar 

  8. W. Saenger, M. Noltemeyer, P. C. Manor, B. Hingerty, and B. Klar: Bioorg. Chem. 5, 187 (1976).

    Google Scholar 

  9. R.J. Bergeron, M.A. Channing, G.J. Gibeily, and D.M. Pillor: J. Am. Chem. Soc. 99, 5146 (1977).

    Google Scholar 

  10. R.J. Bergeron: In J.L. Atwood, J E. Davis, and D.D. MacNicol (eds.): Inclusion Compounds, Vol. 3, Academic Press, London (1984), pp. 391–443.

    Google Scholar 

  11. G. Barone, G. Castronuovo, P. Del Vecchio, V. Elia, and M. Muscetta: J. Chem. Soc. Faraday Trans. I 82, 2089 (1986).

    Google Scholar 

  12. G. Castronuovo, V. Elia, M. Niccoli, F. Velleca and G. Viscardi: Carbohydr. Res. 306, 147 (1998).

    Google Scholar 

  13. S. Andini, G. Castronuovo, V. Elia, and E. Gallotta: Carbohydr. Res. 217, 87 (1991).

    Google Scholar 

  14. G. Castronuovo, V. Elia, A. Iannone, M. Niccoli, and F. Velleca: Carbohydr. Res. 325, 278 (2000).

    Google Scholar 

  15. G. Castronuovo, V. Elia, D. Fessas, F. Velleca, and G. Viscardi: Carbohydr. Res. 287, 127 (1996).

    Google Scholar 

  16. G. Castronuovo, V. Elia, F. Velleca, and G. Viscardi: Termochim. Acta 292, 31 (1997).

    Google Scholar 

  17. G. Barone, G. Castronuovo, V. Elia, V. Di Ruocco, and C. Giancola: Carbohydr. Res. 192, 331 (1989).

    Google Scholar 

  18. G. Castronuovo, V. Elia, D. Fessas, A. Giordano and F. Velleca: Carbohyd. Res. 272, 31 (1995).

    Google Scholar 

  19. L. Paduano, R. Sartorio, V. Vitagliano, and G. Castronuovo: Termochim. Acta 162, 155 (1990).

    Google Scholar 

  20. G. Castronuovo, V. Elia, M. Niccoli, and F. Velleca: ELDATA: Int. Electron. J. Phys.-Chem. Data 3, 63 (1997).

    Google Scholar 

  21. G. Barone, G. Castronuovo, V. Elia, and M. Muscetta: J. Solution Chem. 15, 129 (1986).

    Google Scholar 

  22. G. Barone, G. Castronuovo, V. Elia, and M. Muscetta: Termochimica Acta 85, 443 (1985).

    Google Scholar 

  23. G. Barone, G. Castronuovo, P. Del Vecchio, and V. Elia: In O. Huber and J. Szejtly (eds.), Proceedings of the 4th International Symposium on Cyclodextrins, Kluwer Academic Publisher, Dordrecht (1988).

    Google Scholar 

  24. R. Lumry and Rajender: Biopolymers 9, 1125 (1970).

    Google Scholar 

  25. E.A. Lewis and L.D. Hansen: J. Chem. Soc., Perkhin Trans. II, 2081 (1973).

  26. Y. Inoue, T. Hakushi, Y. Liu, L. Tong, B. Shen, and D. Jin: J. Am. Chem. Soc. 115, 475 (1993).

    Google Scholar 

  27. M. Eftink and R. Biltonen: In A.E. Beezer (ed.), Biological Microcalorimetry, Academic Press, London (1980).

    Google Scholar 

  28. W.G. McMillan Jr. and E. Mayer: J. Chem. Phys. 13, 276 (1945).

    Google Scholar 

  29. J.J. Kozak, W.S. Knight, and W. Kauzmann: J. Chem. Phys. 48, 675 (1945).

    Google Scholar 

  30. H.L. Friedman and V. Krishnan: J. Solution Chem. 2, 119 (1973).

    Google Scholar 

  31. I. Tabushi: In J.L. Atwood, J.E.D. Davies, and D.D. MacNicol (eds.): Inclusion Compounds, Vol. 3, Academic Press, London (1984), pp. 445–471.

    Google Scholar 

  32. M. Bastos, L.E. Briggner, I. Shehatta, and I. Wädso: J. Chem. Thermodyn. 22, 1181 (1990).

    Google Scholar 

  33. J. Li, A. Harada, and M. Kamachi: Bull. Chem. Soc, Jpn. 67, 2808, (1994).

    Google Scholar 

  34. G. Barone, P. Cacace, G. Castronuovo, and V. Elia: J. Chem. Soc. Faraday Trans. I 77, 1569 (1981).

    Google Scholar 

  35. G. Castronuovo, V. Elia, M. Niccoli, and F. Velleca: Thermochim. Acta, in press.

  36. I. Tabuschi, Y. Kiyosuke, T. Sugimoto, and K. Yamamura: J. Am. Chem. Soc. 100, 916 (1978).

    Google Scholar 

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Castronuovo, G., Elia, V., Niccoli, M. et al. The Effects of Cosolvents on the Complexation of α-Cyclodextrin with Alkylated Substances. Calorimetric Studies at 25 °C. Journal of Inclusion Phenomena 44, 229–234 (2002). https://doi.org/10.1023/A:1023019118389

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