SYNTHESIS OF PROPIOLAMIDE AND H-1, C-13 AND N-15 NMR-SPECTRA OF FORMAMIDE, ACETAMIDE AND PROPIOLAMIDE

A high-yield synthesis and purification of propiolamide is described. The structure and purity of the compound were confirmed by 1(H), C-13 and N-15 NMR studies. Natural abundance C-13 and N-15 chemical shift m easurements in 3.0 M acetonitrile solutions are reported along with H- 1-H-1, H-1-N-15 and(1)H-C-13 spin coupling constants. Polarization tra nsfer techniques were used for the N-15 and C-13 measurements. The pro piolamide NMR parameters were compared with those for 3.0 M solutions of formamide and acetamide in acetonitrile solution. Measurements at 2 98 and 278 K indicated that for all three compounds there is still sig nificant rotation about the carbon-nitrogen bond at room temperature. (C) 1997 by John Wiley & Sons, Ltd.