CONFORMATIONS IN UNSYMMETRICALLY N-n-PROPYL-N-SUBSTITUTED 2-PHENYLACETAMIDES

Article abstract of DOI:10.1016/0022-2860(92)80075-S

As a part of a study on the structural characteristics of some new various N-alkyl-N-substituted 2-phenylacetamides the infrared and 1H N.M.R. spectra were obtained and interpreted.The synthesis of a various N-n-propyl-N-alkyl 2-phenylacetamides of the general formula PhCH2CON(nPr)R, wherein R is ethyl, isopropyl, n-butyl, t-butyl and cyclohexyl, were performed.The corresponding mixed secondary amines of the type HNnPrR were obtained by catalytic hydrogenation of the synthetized propylidenealkylamines.The 1H N.M.R. spectra of these unsymmetrically N,N-disubstituted amides have been studied and the peaks have been assigned in each cases to two possible conformational isomers, arising from the lack of free rotation about the C(O)-N bond.These results are in accordance with our previous investigation of the structure of N-substituted 2-phenylacetamides.