Electronic Properties of Anticonvulsant Amides. A C-13 Nuclear Magnetic Resonance Study of Phenylacetanilides

Abstract

Some twenty phenylacetanilides with p-and m-substituents in the aniline ring were prepared and their C-13 nuclear magnetic resonance spectra were measured. Substituent chemical shifts (SCS) of the para-carbon atom were examined by means of dual substituent parameter (DSP) and DSP-nonlinear resonance (DSP-NLR) equations. Excellent correlations were obtained by DSP analyses. The results indicate that the-NHCOCH₂Ph moiety is a weak electron donor. The chemical shift data and derived correlations are very similar to those obtained for substituted propionanilides.