Water interactions were evaluated for all model compounds and PET-derived molecules using geometries shown in Figure . Values of the minimum interaction distance and interaction energy are listed in Tables and. For both BHET and MHET, interaction energies and distances for carbonyl oxygen O4 and the hydroxyl oxygen OE were in very good agreement with QM target data. In case of the ester oxygen O3, interactions were slightly off for the interaction bisecting the lone pairs (O3_180) due to a steric clash caused by a In addition, we evaluated the anisotropic polarizabilities by scanning water interactions along arcs circling the lone pair axis of the carbonyl oxygen and the ester oxygen using MBOA as reference (Figure ). For the majority of the data points, interaction energies and distances were in good agreement with QM target data, although the ester oxygen showed larger deviations of ∼1 kcal/mol for some data points and could be improved in the future by more exhaustively targeting QM polarization anisotropies.