Intrinsic barriers and transition state structures in the gas phase carbon-to-carbon identity proton transfers from nitromethane to nitromethide anion and from protonated nitromethane to aci-nitromethane: an ab initio study

An ab initio study of the identity of carbon-to-carbon proton transfers between nitromethane and nitromethide anion and between oxygen protonated nitromethane and aci-nitromethane was reported. Transition state imbalances were shown to cause slight decrease in intrinsic gas phase barriers. Dependence of the barriers on the pi-acceptor was observed to be a result of complex reactions among resonance, inductive and hydrogen bonding effects.