Solvent effects on the conformations of ortho-substituted acetanilides

Abstract

In acetanilides bearing nitro, halogen, alkoxyl, or carboxyl substituents in the ortho position, the intramolecular hydrogen bond is disrupted by polar solvents and the acetamido group adopts a position out of the plane of the aromatic ring. These changes are studied by means of changes in the deshielding effect of the amide carbonyl group on the remaining ortho proton.