Abstract
The stability constants of the inclusion complexes between 2-hydroxypropyl-β-cyclodextrin and phenolphthalein have been found to decrease with increasing degree of substitution; the hydroxypropylation of the primary rim has a relatively higher effect. The change of specific rotations seems to support this finding. The decrease can be explained by the disturbance of the three-site interaction characteristic for the molecular recognition of phenolphthalein by cyclodextrins.
Similar content being viewed by others
References
L. Szente and D.E. Strattan: Hydroxypropyl-β-cyclodextrins, preparation and physicochemical properties, in:New Trends in Cyclodextrins and Derivatives, D. Duchêne, Ed., Edition de Santé, Paris, pp. 57–96 (1991).
J. Pitha, J. Milecki, H. Fales, L. Pannell and K. Uekama:Int. J. Pharm. 29, 73 (1986).
C.T. Rao, J. Pitha, B. Lindberg and J. Lindberg:Carbohydr. Res. 223, 99 (1992).
T. Irie, K. Fukunaga, A. Yoshida, K. Uekama, H.M. Fales and J. Pitha:Pharm. Res. 5, 713 (1988).
P. Mischnick:Carbohydr. Res. 192, 233 (1989).
J. Pitha, C.T. Rao, B. Lindberg and P. Seffers:Carbohydr. Res. 200, 429 (1990).
C.T. Rao, B. Lindberg, J. Lindberg and J. Pitha:J. Org. Chem. 56, 1327 (1991).
A.R. Hedges and W.J. Shieh, Complexation in modified cyclodextrin compared with unmodified cyclodextrin, in:New Trends in Cyclodextrins and Derivatives, D. Duchêne, Ed., Edition de Santé, Paris, pp. 297–311 (1991).
Á. Buvári, L. Barcza and M. Kajtár:J. Chem. Soc., Perkin Trans. 2, 1687 (1988).
L. Barcza, J. Szejtli and Á. Buvári:Ann. Univ. Sci. Budapest, Sec. Chim. 16, 11 (1980).
H.A. Benesi and J.H. Hildebrand:J. Am. Chem. Soc. 71, 2703 (1949).
Author information
Authors and Affiliations
Additional information
Dedicated to Professor Jószef Szejtli.
Rights and permissions
About this article
Cite this article
Buvári-Barcza, Á., Bodnár-Gyarmathy, D. & Barcza, L. Hydroxypropyl-β-cyclodextrins: Correlation between the stability of their inclusion complexes with phenolphthalein and the degree of substitution. J Incl Phenom Macrocycl Chem 18, 301–306 (1994). https://doi.org/10.1007/BF00708736
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00708736