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The Influence of β- and γ-Cyclodextrin Cavity Size on the Association Constant with Decanoate and Octanoate Anions

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Abstract

This work evaluates the influence of the β- and γ-cyclodextrin (CD) cavity size on the association constant (KCDA) with decanoate (C10) and octanoate (C8) anions. The spectral displacement technique with phenolphthalein was used to obtain the 1:1 association constant (KCDA) in NaHCO3/NaOH buffer pH 10.5 at 25 °C. The KCDA value obtained were 2.6 (±0.2) × 103, 2.5 (±0.5) × 102, for beta;CD–C10 and γCD–C10 inclusion complexes, and 5.1 (±0.2) × 102 and 4.7 (±0.2) × 101 for βCD–C8 and γCD–C8 inclusion complexes, respectively. The KCDA values of either acid with βCD is approximately 10 times higher than for the same acid with γCD, where as for the same cyclodextrin, the KCDA value is 5 times higher for the C10 association than for the C8. The data demonstrate that the cyclodextrin cavity size exerts a greater influence on the association constant than the chain length of the acid for these compounds. 1H NMR studies show that fatty acid protonation has a distinct effect on the chemical shift of CD protons.

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References

  1. J. Szejtli: Cyclodextrin Technology, Kluwer Academic Publishers, Dordrecht (1988), pp. 4-18.

    Google Scholar 

  2. H. Lamparczyk and P. K. Zarzycky: J. Pharm. Biom. Anal. 18, 165 (1998).

    Google Scholar 

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

    Google Scholar 

  4. T. C. Werner and I.M. Warner: J. Incl. Phenom. Mol. Recognit. Chem. 18, 385 (1994).

    Google Scholar 

  5. E. Aicart, F. Mendicuti and E. Junquera: Langmuir 15, 4472 (1999).

    Google Scholar 

  6. E. Aicart and E. Junquera: Int. J. Pharm. 176, 169 (1999).

    Google Scholar 

  7. H-J Schneider, F. Hacket, V. Rüdigger and H. Ikeda: Chem. Rev. 98, 1755 (1998).

    Google Scholar 

  8. L. D. Wilson and R. E. Verrall: Can. J. Chem. 76, 25 (1998).

    Google Scholar 

  9. C.A. Georgiou, S.G. Skoulika and M.G. Polissiou: J. Incl. Phenom. Mol. Recognit. Chem. 34, 85 (1999).

    Google Scholar 

  10. R. E. Verrall, L. D. Wilson and S. R. Siddall: Can. J. Chem. 75, 927 (1997).

    Google Scholar 

  11. L. Barcza, and Á. Buvári: J. Chem. Soc Perkin Trans. 2 1687 (1988).

  12. K. A. Connors: Binding Constants. The Measurement of Molecular Complex Stability, John Wiley & Sons, Canada (1987), pp. 175-180.

    Google Scholar 

  13. J. H. Hildebrand and H. A. Benesi: J. Am. Chem. Soc. 71, 2703 (1949).

    Google Scholar 

  14. J. L. Atwood, J. E. D. Davies and D. D. MacNicol: Inclusion Compounds vol. 3, Academic Press, London (1984), pp. 391-443.

    Google Scholar 

  15. D. A. Laufer, R. I. Gelb, L. M. Schwartz, B. Cardelino, H. S. Fuhrman and R. F. Johnson: J. Am. Chem. Soc. 103, 1750 (1981).

    Google Scholar 

  16. K. A. Connors, H-J. Schneider, V. Rüdigger and A.Gadre: J. Pharm. Sci. 86, 236 (1997).

    Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, Federal University of Santa Catarina, Florianópolis -, SC, 88040 - 900 -, Brazil

    Marcia M. Meier & Bruno Szpoganicz

  2. Food Science and Technology Department, Federal University of Santa Catarina, Florianópolis -, SC, 88040 - 900 -, Brazil

    Marilde T. Bordignon Luiz

  3. Department of Chemistry, University of California, Irvine, Irvine, California, 92697-2025

    Patrick J. Farmer

Authors
  1. Marcia M. Meier
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  2. Marilde T. Bordignon Luiz
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  3. Patrick J. Farmer
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  4. Bruno Szpoganicz
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Meier, M.M., Bordignon Luiz, M.T., Farmer, P.J. et al. The Influence of β- and γ-Cyclodextrin Cavity Size on the Association Constant with Decanoate and Octanoate Anions. Journal of Inclusion Phenomena 40, 291–295 (2001). https://doi.org/10.1023/A:1012705301448

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