N- vs. C-protonation of captodative trifluoromethylated enamines: A theoretical study

A study of the effect of stereoelectronic structure of captodative enamines on protonation site has been carried out by means B3LYP/6-311G**, B3LYP/6-311++G** and MP2/6-311G**//B3LYP/6-311G** calculations. The presence of CF3 group in trifluoromethylated enamines levels the energy of their N- and C-protonation. Its value and regioselectivity of protonation depends on both the nature of amine moiety and the solvent.