Proton transfer and coordination properties of aromatic α-hydroxy hydrazones

Abstract

The prototropic properties of two nitro derivatives of aromatic α-hydroxy hydrazones [2,4-dinitro- N-phenyl- N′(2-hydroxy-1-phenylmethylene hydrazine) and 2,4-dinitro- N-phenyl- N′(2-hydroxy-1-naphthylmethylene hydrazine] have been analysed through electronic absorption, 1H and 13C NMR and semiempirical molecular orbital methods. The metal binding properties of both compounds and of the unsubstituted hydrazones were evaluated from potentiometric and spectrophotometric data in dioxane–water mixtures. On the basis of the spectral analysis and PM3 semiempirical calculations, the structures of the formed complexes were proposed.