Synthesis, structural and spectroscopic properties of asymmetric Schiff bases derived from 2,3-diaminopyridine

Two Schiff base derivatives, 4-(2-amino-3-pyridyliminomethyl)phenol (I) and 3-(2-amino-3-pyridyliminomethyl)nitrobenzene (II), were synthesised and characterised by spectroscopy. The structure of I was determined by single crystal X-ray diffraction studies. The asymmetric Schiff base derived from 2,3-diaminopyridine selectively recognise transition and heavy metal cations, and some anion. Ligands I and II form stable complexes with Cu2+, Zn2+, Pb2+, Al3+ whereas ligand I also binds F~ ions. The stoichiometry for the host: cation is 1: 1 and 2: 1. The addition of F~ ion in CH3CN to ligand I causes a colour change of the solution from colourless to yellow. The binding behaviour of ligand I towards several ions was investigated using density functional theory calculations.