HYDROGEN-BONDING .32. AN ANALYSIS OF WATER-OCTANOL AND WATER-ALKANE PARTITIONING AND THE DELTA-LOG-P PARAMETER OF SEILER

A general linear solvation energy equation has been used to analyze published partition coefficients in the systems water-octanol (613 solutes), water-hexadecane (370 solutes), water-alkane (200 solutes), and water-cyclohexane (170 solutes). The descriptors used in the equation are R(2), an excess molar refraction; pi(2)(H), the solute dipolarity/polarizability; Sigma alpha(2)(H) and Sigma beta(2)(H), the effective solute hydrogen-bond acidity and basicity; and V-X, the characteristic volume of McGowan. It is shown that the water-octanol partition coefficient is dominated by solute hydrogen-bond basicity, which favors water, and by solute size, which favors octanol, but solute excess molar refraction and dipolarity/polarizability are also significant. For the water-alkane partition coefficients, the same factors are at work, together with solute hydrogen-bond acidity as a major influence that favors water. An analysis of 288 Delta log P values shows that solute hydrogen-bond acidity is the major factor but that solute hydrogen-bond basicity and, to a lesser extent, solute dipolarity/polarizability and size are also significant factors that influence the Delta log P parameter.