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The inclusion of diflunisal by γ-cyclodextrin and permethylatedβ-cyclodextrin. A UV-visible and19F nuclear magnetic resonance spectroscopic study

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Abstract

The complexation of the diflunisal anion (DF) by γ-cyclodextrin (γCD) and permethylatedβ-cyclodextrin (βPCD) in aqueous solution at pH 7.00 at 298.2 K, has been studied by UV-visible and19F NMR spectroscopy. The formation of 1∶1 and 1∶2 γCD inclusion complexes proceeds through the two equilibria:

$${\text{DF + }}\gamma {\text{CD}} \rightleftharpoons {\text{DF}} \cdot \gamma {\text{CD}}$$
((K1))
$${\text{DF}} \cdot \gamma {\text{CD + }}\gamma {\text{CD }} \rightleftharpoons {\text{ DF}} \cdot {\text{(}}\gamma {\text{CD)}}_{\text{2}} {\text{ }}$$
((K2))

characterised byK 1=(5.5±0.2)×104 dm3 mol−1 andK 2=(2.3±0.2)×104 dm3 mol−1 derived from UV-visible spectrophotometric data. The analogous βPCD complexes are characterised byK 1=(6.86±0.02)×104 dm3 mol−1 andK 2=(8.75±2.7)×101 dm3 mol−1. The variation of the19F chemical shift of DF on inclusion is consistent with the formation of 1∶1 and 1∶2 complexes also. Comparisons with related systems are made.

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Authors and Affiliations

  1. Department of Physical and Inorganic Chemistry, University of Adelaide, 5001, South Australia, Australia

    Stephen F. Lincoln, Andrea M. Hounslow, John H. Coates, Rosa P. Villani & Robert L. Schiller

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  1. Stephen F. Lincoln
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  2. Andrea M. Hounslow
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  3. John H. Coates
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  4. Rosa P. Villani
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  5. Robert L. Schiller
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Lincoln, S.F., Hounslow, A.M., Coates, J.H. et al. The inclusion of diflunisal by γ-cyclodextrin and permethylatedβ-cyclodextrin. A UV-visible and19F nuclear magnetic resonance spectroscopic study. Journal of Inclusion Phenomena 6, 183–191 (1988). https://doi.org/10.1007/BF00663051

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  • DOI: https://doi.org/10.1007/BF00663051

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