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Thermodynamics of Nicotinic Acid Interactions with Some Saccharides

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Abstract

The interactions of nicotinic acid with α-D-glucose and maltose, and with α-, β-, hydroxypropyl-α- and hydroxypropyl-β-cyclodextrins were studied by using solution calorimetry at T = 298.15 K and pH = 3.4. The thermodynamic parameters (log10 K, Δ Gc, Δ Hc and Δ Sc) were calculated for the systems in which complex formation was observed. Systems with weak interparticle interactions lacking complex formation were characterized by enthalpic virial coefficients calculated on the basis of the McMillan–Mayer theory. It was found that the complexation affinity of α-cyclodextrin to nicotinic acid is stronger in comparison to β-cyclodextrin and the mono- and disaccharides. The influence of different factors, such as the availability of the macrocyclic hydrophobic cavity, the relationship of the sizes of guest molecule to the host cavity, the presence of bulky hydroxypropyl substitutes and their structure, and the solvation of guest molecules on the stability of complexes and their thermodynamic parameters of interaction is discussed.

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References

  1. D. Menon, D. Dollimore, and K. S. Alexander, Thermochim. Acta 392–393, 237 (2002).

    Google Scholar 

  2. J. Szejtli and T. Osa, Eds. Cyclodextrins, in Comprehensive Supramolecular Chemistry, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, and F. Vögtle, eds., (Pergamon, Oxford, 1996), V. 3.

  3. A. R. Hedges, Chem. Rev. 98, 2035 (1998).

    Article  CAS  Google Scholar 

  4. S. El Gezawi, N. Omar, N. El Rabbat, H. Ueda, and J. H. Perrin, J. Pharm. Biomed. Anal. 6, 399 (1988).

    CAS  Google Scholar 

  5. Y. A. Zhdanov, E. V. Kompantseva, Y. E. Alekseev, L. P. Ovcharenko, E. L. Korol, and T. P. Sudareva, Dokl. Russ. Acad. Sci. 344, 197 (1995).

    CAS  Google Scholar 

  6. E. A. Lewis and L. D. Hansen, J. Chem. Soc., Perkin Trans. 2, {2081} (1973).

    Google Scholar 

  7. D. Ferej-Temeljotov, M. Kmet, D. Kocjan, S. Kotnik, A. Resman, U. Urleb, K. Verhniak, I. Zver, and J. Zmitek, Chirality 4, 288 (1993).

    Google Scholar 

  8. M. V. Rekharsky, E. V. Nemykina, A. V. Eliseev, and A. K. Yatsimirsky, Thermochim. Acta 202, 25 (1992).

    Article  Google Scholar 

  9. V. Terekhova, O. V. Kulikov, and E. S. Titova, Thermochim. Acta 412, 121 (2004).

    Article  CAS  Google Scholar 

  10. V. Terekhova and O. V. Kulikov, Russ. Chem. Bull. 48, 2259 (1999).

    CAS  Google Scholar 

  11. V. A. Borodin, E. V. Kozlovsky, and V. P. Vasil'ev, Russ. J. Inorg. Chem. 27, 2169 (1982).

    CAS  Google Scholar 

  12. A. Lesley and J. Bullock, J. Chem. Soc., Faraday Trans. 1 78, 1177 (1982).

    Google Scholar 

  13. R. M. Smith and A. E. Martell, Critical Stability Constants (Plenum Press, London, 1976), Vol. 1, p. 3.

    Google Scholar 

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

    Article  CAS  Google Scholar 

  15. E. Desnoyers, G. Perron, and L. Avedikian, J. Solution Chem. 5, 631 (1976).

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  17. A. Connors, Chem. Rev. 97, 1325 (1997).

    Article  CAS  Google Scholar 

  18. V. Rekharsky and Y. Inoue, Chem. Rev. 98, 1875 (1998).

    Article  CAS  Google Scholar 

  19. H.-J. Schneider, F. Hacket, and V. Rudiger, Chem. Rev. 98, 1755 (1998).

    Article  CAS  Google Scholar 

  20. B. Lipkowitz, J. Org. Chem. 56, 6357 (1991).

    CAS  Google Scholar 

  21. S. P. van Helden, M. J. van Drooge, A. J. Claessens, A. C. A. Jansen, and L. M. H. Janssen, Carbohydr. Res. 215, 251 (1991).

    Article  CAS  Google Scholar 

  22. L. Liu and Q.-X. Guo, J. Inclus. Phen. Macrocycl. Chem. 42, 1 (2002).

    CAS  Google Scholar 

  23. H. S. Frank and M. W. Evans, J. Chem. Phys. 13, 507 (1945).

    CAS  Google Scholar 

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Correspondence to Irina V. Terekhova.

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Terekhova, I.V., Obukhova, N.A. Thermodynamics of Nicotinic Acid Interactions with Some Saccharides. J Solution Chem 34, 1273–1282 (2005). https://doi.org/10.1007/s10953-005-8018-9

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  • DOI: https://doi.org/10.1007/s10953-005-8018-9

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