GEOMETRICAL CONSEQUENCES OF RESONANCE-ASSISTED HYDROGEN-BONDING IN 2-NITROVINYL ALCOHOL AND INDICATION OF A SLIGHT ATTRACTIVE O-CENTER-DOT-CENTER-DOT-CENTER-DOT-H INTERACTION IN 2-NITROETHANOL - AN AB-INITIO MOLECULAR-ORBITAL INVESTIGATION

Ab initio molecular orbital calculations on 2-nitrovinyl alcohol and 2 -nitroethanol and their parent structures have been performed with a 6 -31G* basis set, including electron correlation using second-order Mo ller-Plesset perturbation theory. There is resonance-assisted hydrogen bonding in 2-vinyl alcohol, as witnessed by a 1.75 Angstrom long O .. . H interaction and considerable bond length changes in the rest of th e molecule, as compared with nitroethylene and vinyl alcohol. Slight b ond length changes in 2-nitroethanol point to some attractive O ... H interaction even in 2-nitroethanol.