Synthesis and FTIR spectroscopic study of some N-monosubstituted propanamides

Article abstract of DOI:10.1016/S0022-2860(96)09743-8

In the present work we investigated the conformations of some N-mono-substituted propanamides of general formula CH₃CH₂CONHR, wherein R is chosen from n-(C₁-C₉)alkyl, cyclo(C₃-C₆)alkyl, some branched (C₃-C₆)alkyl or phenyl. The amides were synthesised by the well known Schotten-Baumann reaction-acylation of the corresponding amines with propionyl chloride. On the basis of FTIR data for diluted solutions (concentrations below 10^-3 mol dm^-3) of N-mono-substituted propanamides in carbon tetrachloride, chloroform, dichloromethane, or a 1:1.5 mixture of benzene and carbon tetrachloride the exact position of the N-H stretching band was established. For spectroscopic data the different conformational isomers were assigned and its structures unequivocally proven. These results are in good accordance with ¹H NMR and MS data.