Hydrogen-Bonding Abilities for Phenols Assessed by Quantitative Analyses of Their Partition Coefficients Derived from Different Partitioning Systems

Abstract

We recently proposed a new hydrogen-accepting scale, S_HA, on the basis of the heat of formation calculated by the conductor-like screening model (COSMO) method. In this work, the same approach was applied to a series of compounds with a common hydrogen-donor group. Thus the S_HA values for monosubstituted phenols were calculated and used for correlating their log P_oct values (P_oct: 1-octanol/water partition coefficient) with log P_CL (P_CL: chloroform/water partition coefficient) and log P_E (P_E: butyl ether/water partition coefficient). It was demonstrated that the S_HA parameter works effectively, providing excellent correlations whose physicochemical meanings are well rationalized in terms of hydrogen-bonding characteristics of the substituents.