Determination of Lipophilicity of Chlorinated Alicyclic Compounds by Reversed-Phase High Performance Liquid Chromatography

Abstract

A RP-HPLC procedure has been developed for measuring the capacity factor (k′) of a series of chlorinated alicyclic compounds. The chromatographic behavior measured on a 4.5 mm i.d. × 3.3 cm C-18 column with methanol/water as the mobile phase was related to the volume fraction of methanol (φ). A linear relationship was found between log k′ and φ, showing the correlation coefficient γ > 0.99, for each of the 15 chlorinated alicyclic compounds tested. The log k_w, the capacity factor obtained by extrapolation of the retention data from binary eluents to 100 % water, was chosen as a measure of the solute lipophilicity. Since log k_w is considered as a valuble index of the lipophilicity of a compound, the determined values will be used for the quantitative structure-activity relationship studies of the chlorinated alicyclic compounds.