Can Lone Pairs Bind to a π System? The Water···Hexafluorobenzene Interaction

Abstract

Ab initio calculations reveal a significant binding interaction between water and hexafluorobenzene in a geometry that points the oxygen lone pairs directly into the face of the π system. The geometry is as anticipated from electrostatic arguments emphasizing the substantial quadrupole moment of the aromatic. A second, off-axis geometry is also found which is also consistent with a substantial electrostatic interaction.