Alcohol associates as catalysts of tautomeric transformations

Abstract

The B3LYP/6-311++G(df,p) quantum-chemical simulation has revealed that linear associates of methanol catalyze the ketone-enol, nitro-aci-nitro, and carbamate-azomethinenol tautomeric transformations. All the reactions proceed via the coherent transition states. The catalytic effect is enhanced with the increased alcohol degree of association. The acid-base properties of methanol are changed similarly.

Reactivity of hydrogen-bonded complexes of water, methanol, phenol and methyl amine

“…91 The enhanced acid–base properties of alcohol associates lead to the fact that they catalyze tautomeric transformations much more efficiently than alcohol monomers. 92 Thus, alcohol associates exhibit an increased reactivity in comparison with monomers in a wide variety of reactions.…”