Tetrahedron

NMR spectra of intramolecularly hydrogen-bonded compounds—II: Schiff bases of β-diketones and o-hydroxycarbonyl compounds

NMD Brown, DC Nonhebel

Index: Brown,N.M.D.; Nonhebel,D.C. Tetrahedron, 1968 , vol. 24, p. 5655 - 5664

Full Text: HTML

Citation Number: 94

Abstract

Schiff bases of aromatic amines and β-diketones including those containing Ph end-groups have been shown to exist as the keto-amine tautomer using NMR spectroscopy. The Schiff bases derived from aromatic amines and 2-hydroxyl-1-naphthaldehyde were concluded to be an equilibrium mixture of the ketoenamine and enolimine forms. The influence of electronic effects in the aromatic amines on the hydrogen-bond strength was also ...