Bimolecular reactions of nucleophiles in the gas phase. The reaction of the methoxide anion with ketones. An ion cyclotron resonance study

Abstract

The methoxide anion (produced from methyl nitrite) reacts with neutral ketones (M) to form non-decomposing(M-H⁺)^- ions. The (M-H⁺)^- ions are ambident species and they undergo a number of ion-molecule reactions, including (i) characteristic reactions through the carbanion centre with methyl nitrite, and (ii) for acetone, the formation of an [M +(M- H⁺)]^- ion. In several cases peaks due to collision-stabilized (M+MeO^-) ions are observed (e.g. MeO^-/acetone), but they are not detected for the majority of cases studied.