Stability constants of α-cyclodextrin complexes of para-substituted aromatic ketones in aqueous solution

(Note: The full text of this document is currently only available in the PDF Version )

D. Martin Davies, Michael E. Deary and David I. Wealleans


Abstract

Stability constants for α-cyclodextrin complexes of 21 para-substituted acetophenones and related aryl ketones have been determined spectrophotometrically or potentiometrically. It has been found that the presence of ketone-containing substituents generally results in destabilisation of complex formation. It is postulated that steric hindrance at the narrow end of the cyclodextrin cavity causes the benzene ring to be displaced from its optimal position or orientation.


References

  1. G. Wenz, Angew. Chem., Int. Ed. Engl., 1994, 33, 803 CrossRef.
  2. Y. Inoue, Ann. Rep. NMR Spectrosc., 1993, 27, 59 Search PubMed.
  3. (a) D. M. Davies and J. R. Savage, J. Chem. Res. (S), 1993, 94 Search PubMed; (b) D. M. Davies and J. R. Savage, J. Chem. Res. (M), 1993, 660 Search PubMed.
  4. D. M. Davies and M. E. Deary, J. Chem. Soc., Perkin Trans. 2, 1995, 1287 RSC.
  5. D. M. Davies and M. E. Deary, J. Chem. Soc., Perkin Trans. 2, 1996, 2423 RSC.
  6. M. Sakurai, M. Kitagawa, H. Hoshi, Y. Inoue and R. Chujo, Chem. Lett., 1988, 895 CAS; M. Sakurai, M. Kitagawa, H. Hoshi, Y. Inoue and R. Chujo, Carbohydr. Res., 1990, 198, 181 CrossRef CAS.
  7. O. S. Tee, A. A. Fedortchenko, P. G. Loncke and T. A. Gadosy, J. Chem. Soc., Perkin Trans. 2, 1996, 2, 1243 RSC.
  8. D. M. Davies and M. E. Deary, J. Chem. Soc., Perkin Trans. 2, 1996, 2415 RSC.
  9. S.-F. Lin and K. A. Connors, J. Pharm. Sci., 1983, 72, 1333 CrossRef CAS.
  10. M. Charlton and I. Motoc, Top. Curr. Chem., 1983, 114, 2; A. Verloop and J. Tipker, in QSAR in Drug Design and Toxicology, ed. D. Hadzi and B. Jerman-Blazic, 1987, p. 97, Elsevier Science Publishers B.V., Amsterdam Search PubMed; T. Fujita and H. Iwamura, Top. Curr. Chem., 1983, 114, 119 Search PubMed.
  11. D. M. Davies and J. R. Savage, J. Chem. Soc., Perkin Trans. 2, 1994, 1525 RSC.
  12. K. Harata, Bull. Chem. Soc. Jpn., 1976, 49, 2066 CAS.