Are the O–H⋯H–C intramolecular systems of 2-cyclopropyl ethenol and its derivatives classified as dihydrogen bonds? Ab initio and DFT study

Abstract

MP2/6-311++G(d,p) and B3LYP/6-311++G(d,p) calculations on 2-cyclopropyl ethenol and its fluoro derivatives have been performed showing the existence of H⋯H intramolecular contacts which are slightly shorter than the corresponding sum of van der Waals radii. The molecular structures of these species have been compared with the corresponding conformers for which such contacts do not exist. The net atomic charges derived from the Mulliken population analysis were analyzed and the Bader theory was applied to discuss if H⋯H contacts of analyzed systems may be classified as intramolecular dihydrogen bonds.