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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.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

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 Coefficients1)