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

✍ Scribed by Zihni Aksaç; Esat Pinar; Sîddîk Içli

Publisher
John Wiley and Sons
Year
1983
Tongue
English
Weight
396 KB
Volume
21
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

3‐Aryl‐2‐thioxo‐4‐oxazolidinones and 3‐arylrhodanines have been studied for magnetic non‐equivalence of diastereotopically related proton and ^13^C 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 ^1^H and some ^13^C nuclei.

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