Strong C-H/O interactions between polycyclic aromatic hydrocarbons and water: Influence of aromatic system size

Abstract

Energies of C-H/O interactions between water molecule and polycyclic aromatic hydrocarbons with a different number of aromatic rings were calculated using ab initio calculations at MP2/cc-PVTZ level. Results show that an additional aromatic ring in structure of polycyclic aromatic hydrocarbons significantly strengthens C-H/O interactions. Calculated interaction energies in optimized structures of the most stable tetracene/water complex is -2.27 kcal/mol, anthracene/water is -2.13 kcal/mol and naphthalene/water is -1.97 kcal/mol. These interactions are stronger than C-H/O contacts in benzene/water complex (-1.44 kcal/mol) while C-H/O contacts in tetracene/water complex are even stronger than C-H/O contacts in pyridine/water complexes (-2.21 kcal/mol). Electrostatic potential maps for different polycyclic aromatic hydrocarbons were calculated and used to explain trends in the energies of interactions. (C) 2017 Elsevier Inc. All rights reserved.