A theoretical study of adduct formation between methanolate and Propan-2-one

Abstract

Ab initio molecular orbital calculations at the STO-3G level of approximation predict that the methoxide anion bonds through its oxygen atom to form complexes with acetone in at least three different ways:

(i) A tetrahedral adduct at the carbonyl carbon (ΔE -262 kJ mol^-1).

(ii) A hydrogen-bond complex with a single hydrogen of one methyl group (- 100 kJ mol^-1).

(iii) A symmetrical bidentate hydrogen-bond complex with a hydrogen from each acetone methyl group (- 143 kJ mol^-1).