Abstract
Syntheses of 2-phenyliminomethylphenols (I) and 2-phenylaminomethylphenols (II) are described. Acid dissociation constants, determined potentiometrically, for the amines (II) are related to substituent constants; values are not obtained for Schiff bases(I) due to their hydrolysis. IR spectra of the amines (II) indicate chelate ring formation via OH⋯N hydrogen bonding. NMR spectra for Schiff bases (I) are consistent with the phenol-imine tautomer, not the ketone-amine tautomer. Ligands (I) form bis-complexes with copper(II) while the amines (II) form copper(II) complexes in the presence of acetate anion; magnetic measurements for these indicate no metal-metal interaction in the solid state.
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