Abstract
Hindered rotation around the CN-bond of the thioamid group and the NC aryl-bond in o-substituted N-alkyl thioformanilides has been investigated by NMR spectroscopy. The (E)/(Z)-isomer ratio depends on the electrostatic interaction of the thiocarbonyl group and the ortho substituent, and the size of the N-alkyl group. Concerning symmetry operations the chemical shift difference in the NMR signals of the geminal groups of prochiral N-alkyl substituents has been reduced to the anisotropy and the property of the ortho substituent, to withdraw electrons from the aromatic nucleus.
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