The Open Chemical Physics Journal

2008, 1 : 36-41
Published online 2008 June 3. DOI: 10.2174/1874412500801010036
Publisher ID: TOCPJ-1-36

Molecular Interaction Potential with Polarization (MIPp) Study of the Interplay Between Ion-π and Hydrogen Bonding Interactions

David Quiñonero , Daniel Escudero , Antonio Frontera and Pere M. Deyà
Department of Chemistry, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122 Palma de Mallorca, Baleares, Spain.

ABSTRACT

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.