Enthalpies, Free Energies, and Entropies of Transfer of Phenols from Nonpolar Solvents to Water

Article abstract of DOI:10.1021/j150653a049

The enthalpies of transfer of seven phenols from 1-octanol to water and from toluene to water were determined by calorimetry.In the case of two phenols, whose rate of solution in water was found to be too slow for measurement by the usual heat of solution method, a new two-phase titration method was employed.The free energies of transfer between these solvents were determined by measuring the appropriate partition coefficients.The nature of the nonpolar solvent (toluene or 1-octanol) was found to cause large changes in the average values of the thermodynamic parameters of transfer into water, as well as changes in the ordering of the phenols in the series with respect to these transfer parameters.A curious correlation was observed between the octanol-water partition coefficients and the toluene -> water entropies of transfer.