Hydrophobicity Parameters Determined by Reversed-Phase Liquid Chromatography.
XVI: A New Hydrogen-Accepting Parameter for Monosubstituted Thiophenes and Furans for Correlating Retention Factors and Octanol–Water Partition Coefficients

Abstract

We recently proposed a new hydrogen-accepting parameter, S_HA, for monosubstituted (di)azines on the basis of the heat of formation calculated by the conductor-like screening model (COSMO) method. In this work, S_HA values for monosubstituted thiophenes and furans were calculated and the results were applied to the analysis of relationships between log P (P: 1-octanol/water partition coefficient) and log k (k: retention factor obtained by reversed phase HPLC). The S_HA parameter was found to work effectively as a hydrogen-bonding parameter in a range of heteroaromatic compounds.