The interplay between cation-π and hydrogen bonding interactions involving aromatic rings is studied by
means of Molecular Interaction Potential with polarization (MIPp) calculations. We have analyzed the effect of the participation
of the aromatic in hydrogen bonding interactions on the ion-binding affinity of the arene, by means of Molecular
Electrostatic Potential (MEP), MIPp and ab initio calculations. We have observed that when the aromaric ring participates
in hydrogen bonding interaction as hydrogen bond (HB) donor its capacity for interacting with cations (cation-π interaction)
augments. In addition when the arene is forming hydrogen bonding interactions as HB acceptors, the capacity of
the aromatic ring for interacting with anion increments (anion-π interaction). This mutual influence of cation-π and HB interactions
is studied and analyzed by means of the MIPp partition scheme.