Interfacial effects in the solubilization of o-, p-substituted phenols

The solubilization of ortho and para isomers of substituted phenols such as nitro phenols, chlorophenols, cresols and isopropylphenols in anionic micelles is reported. A comparison of the free energy of micellar solubilization provides an insight into the effect of the nature and position of the substituent. The solubilization of the ortho substituted phenols was found to be energetically more favourable than that of corresponding para isomers when the substituent was polar in nature (nitropheols and chlorophenols). Conversely, phenols with nonpolar substituents (cresols and isopropylphenols) resulted in the para isomer being more favourably solubilized by the micelles.