Abstract
2-Deuterated anilides demonstrate a significant upfield shift of the remaining 6- proton in their 1H-NMR spectra. This is occasioned by a preference for the conformation in which the deuteron is adjacent to the anilide carbonyl group. The electronic effects in this system have been investigated by the preparation of a range of structural variants. The results are consistent with a hydrogen-bonding hypothesis but further work is required to investigate alternative explanations.