The lipophilicity of a series of phenolic compounds was studied in the 1,2-dichloroethane (1,2-DCE)/water system. Cyclic voltammetry at the ITIES was used to study the transfer characteristics of the
charged species, and their partition coefficient was deduced from their formal transfer potential. For the neutral
species, log P
DCE values were measured by a two-phase pH-metric method. The results are compared to those
previously obtained in octanol/water and by linear solvation energy relationships (LSER) in the two solvent
systems. It is shown that nitrophenols with intramolecular H-bonding deviate from the solvatochromic equation
for the 1,2-DCE/water system, and discrepancies between both approaches are discussed on the basis of
conformational and steric effects. When charged however, all the species have approximately the same partition
coefficients because the effect of the intramolecular H-bond disappears and the differences in measured
lipophilicity arise from the variation of the intramolecular charge delocalization due to resonance equilibria.
Some biological implications of these properties are discussed.
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