Is there an O–H⋯C hydrogen bond in the cation of ciso-cresol?

Abstract

Ab initio and DFT geometry optimization, followed by the application of Bader’s theory atoms in molecules (AIM) have been applied to probe the proposed O–H⋯C3– hydrogen bond in cis o-cresol. No evidence was found to support the presence of such novel type hydrogen bond. It is concluded that the observed ir frequency shift (25 cm −1) should be explained by some other means.