Correlation Between Inclusion Formation Constant and Distribution Coefficient in a Liquid–Liquid Extraction System Consisting of Hydrocarbon Solvents and Aqueous Dimethyl Sulfoxide Solutions of β-Cyclodextrin

Abstract

Carbazole was used as a fluorescence probe for the investigation of the correlation between the apparent formation constant (K_f) for an inclusion complex of β-cyclodextrin (CD) and the distribution coefficient (K_d) on liquid–liquid extraction. Single batch extractions of carbazole were performed at 25 ± 1 °C from three types of hydrocarbon solvents into an aqueous dimethyl sulfoxide (DMSO) phase containing CD or nothing. Both the K_f and K_d values for carbazole can be determined simultaneously under the same conditions on the basis of the extraction data. A plot of log K_f versus log K_d gives a straight line in both extraction systems of heptane and dodecane, with good correlations (0.9996 and 0.9992) and similar slopes (-0.675 and -0.672). The experimental results obtained from the cyclohexane–aqueous DMSO system suggest that the hydrocarbon used as the organic phase competes with carbazole for complexation with CD. The linear relationship is embodied in the form of an empirical equation, log K_fOB = -0.673 log K_d + log (K_fCR/K_fHY), where K_fOB is the observed K_f value for a 1:1 carbazole–CD complex in the aqueous DMSO medium and K_fCR and K_fHY are the absolute K_f values in water for the carbazole– and hydrocarbon–CD complexes, respectively.

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