Effects of solvents on the tautomerization of N,N-dimethylglycine

Abstract

The effects that solvents have on the tautomerization of N,N-dimethylglycine are analyzed and the solvent's dipolarity/ polarizability and acidic properties appear to play important roles in the solvation of the zwitterionic tautomer. Owing to the existence of a stable intramolecular hydrogen-bonded conformer of the zwitterion, in which the acidic hydrogen of the ion is hydrogen bonded to the carboxylate functionality, solvation of the zwitterion by basic solvents is not very important.