1H and 13C NMR studies on 3-aryl-2-thioxo-4-oxazolidinones and 3-arylrhodanines

3-Aryl-2-thioxo-4-oxazolidinones and 3-arylrhodanines have been studied for magnetic non-equivalence of diastereotopically related proton and ¹³C nuclei in rotational isomers, and for steric interactions between the aryl and heterocyclic moieties of these compounds. For the majority of rotational isomers the barriers to internal rotation about the aryl C? N bond were >100 kJ mol^?1, due to the steric bulk of the thiocarbonyl group. Chemical isolation of several of the diastereomers was achieved. The enhanced steric effect and the difference in the electronic effect of the sulphur atom in relation to the oxygen atom appeared to have no influence on the small chemical shift differences of the rotational isomers, detected for some ¹H and some ¹³C nuclei.