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

作者：Chipanina N N^*; Aksamentova T N; Shainyan B A; Rulev A Yu

来源：Journal of Molecular Structure (Theochem), 2010, 947(1-3): 22-31.

DOI：10.1016/j.theochem.2010.01.033

• Captodative enamine
• Protonation
• DFT
• B3LYP

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 MP2/6-311GB3LYP/6-311G** calculations. The presence of CF(3) 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.

• 出版日期2010-5-15