Intramolecular electronic and hydrogen-bonding interactions in N,N'-dimethyl-2,3-di-O-methyl-L-tartaramide

The changes in energy of the N,N'-dimethyl-2,3-di-O-methyl-L-tartaramide, model compound of polytartaramides based on 2,3-di-O-methyl-L-tartaric acid and 1,n-alkanediamine, have been analyzed by ab initio quantum mechanical calculations. The influences of the gauche oxygen effect have been investigated in the gas phase as well as in aqueous, chloroform, and carbon tetrachloride solutions. The results indicate that polarizable environments enhance the gauche oxygen effect, but the amount of stabilization depends on the electronic characteristics of the solvent.