COMPUTATIONAL INVESTIGATIONS OF CARBONYL REACTIONS: COMPARISON BETWEEN NUCLEOPHILIC ADDITION VERSUS ENOLATE FORMATION IN THE REACTION OF ACETALDEHYDE WITH HYDROXIDE ION

摘要

Reaction pathways leading to nucleophilic addition and enolate formation were investigated for the reaction between acetaldehyde and hydroxide anion. Ab initio calculations predict small activation barriers for both reactions in the gas phase. Monte Carlo simulations were performed to assess the effects of aqueous solvation. It was found that both reaction pathways involve significant solvent-induced activation barriers, in addition to effecting some structural changes in the transition state.