N. Chipanina, A. Y. Rulev, L. V. Sherstyannikova
Nov 1, 2003
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Journal
Russian Journal of Organic Chemistry
Abstract
According to the data of UV, IR, 1H and 13NMR spectra and also quantum-chemical calculations (B3LYP/631G*), Z- and E-isomers of 2-diethylamino-3-phenylpropenal in inert environment exist as antiperiplanar conformers. The energy of electron transitions therein depends on the orientation both f the benzene ring and the unshared electron pair of the nitrogen with respect to the C = C bond. 2-Diethylamino-3-phenylpropenal is an enamine, but the extent of the pπ* interaction in its prevailing Z-isomer is small.