Chiral recognition of the Schiff bases by NMR spectroscopy in the presence of a chiral dirhodium complex. Deuterium isotope effect on 13C chemical shift of the optically active Schiff bases and their dirhodium adducts

Abstract

The dirhodium method has been successfully applied in chiral recognition of the optically active Schiff bases, derivatives of ortho-hydroxyaldehydes existing in the NH-form. or at tautomeric equilibrium. The position of the equilibrium of Schiff bases as well as their adducts has been established on the basis of measurements of deuterium isotope effects on 13C chemical shifts. The presence of the proton transfer equilibrium or NH-tautomer has promoted the adduct formation. At the equilibrium state, formation of the adducts has shifted the proton transfer equilibrium towards the NH-form. The binding site was the oxygen atom of the proton donor group.