Solvation of H3O+ by phenol:: Hydrogen bonding vs π complexation

Ab initio calculations at the second-order Moller-Plesset perturbation theoretic level have been carried out to study the solvation of protonated water by phenol molecules. The results show that in addition to classical O-H center dot center dot center dot O hydrogen bonds, C-H center dot center dot center dot O, pi center dot center dot center dot H-O, and pi center dot center dot center dot H-C bonds are also formed, thus stabilizing the H3O+(C6H5OH)(3) complex.