The effect of hydrogen bonding on the π depletion and the π-π stacking interaction.

Non-covalent interactions such as hydrogen bonding and π-π stacking are essential types of interactions governing molecular self-assembly. The π-π stacking ability of aromatic rings depends on the electron density of the π orbitals, which is affected by the electron-withdrawing or electron-donating properties of the substituents. We have here studied the effect of hydrogen bonding on the strength of the π-π stacking interactions by calculating the binding energies at the explicitly correlated Møller-Plesset (MP2-F12) perturbation theory level using polarized triple-