Analysis of the Orbital and Electrostatic Contributions to the Lone Pair–Aromatic Interaction Using Molecular Rotors

The attractive interaction between carbonyl oxygens and the π-face of aromatic surfaces was studied using N-phenylimide molecular rotors. The C═O···Ar interactions could stabilize the transition states but were half the strength of comparable C═O···C═O interactions. The C═O···Ar interaction had a significant electrostatic component but only a small orbital delocalization component.