Solvent effect on ternary complexes formed by epoxy and hydrofluoric acid

Abstract

The solvent effect on derivatives of the C2H4O∙∙∙HF∙∙∙HF ternary complex was investigated through the PCM approach and AGOA calculations at the B3LYP/6-311++G(d,p) level of theory. The continuous analysis was useful to verify the profiles of the hydrogen bond distances in the complex, specifically the O∙∙∙H, F∙∙∙H, and F∙∙∙Hβ contacts. On the viewpoint of AGOA, the configurations of the water molecules followed by the measurement of the discrete hydration energies were unveiled.Through the single point energy calculation, the hydration energies were determined through the supermolecule approach, whose values were corrected by the counterpoise correction of the Basis Sets Superposition Error (BSSE). In line with this, the analysis of the Molecular Electrostatic Potential (MEP) revealed positive and negative regions, which represent the interaction sites for the water molecules regarding the oxygen and hydrogen, respectively. In an overview, the acid-catalyzed epoxy ring-opening reaction has distinct interpretations either in vacuum or in aqueous medium whether the most appropriate structure of the C2H4O∙∙∙HF∙∙∙HF trimolecular complex is taken into account.

Keywords

• hydrogen bonds
• oxirane
• hydrofluoric acid
• PCM
• AGOA