Conformational and spectroscopic investigation of 3-hydroxyflavone–aluminium chelates

3-Hydroxyflavone (3HF), which is the simplest molecule of the flavonol class, possesses chelating properties towards Al(III). Spectrophotometric methods have shown that the 3HF molecule forms an Al(3HF) 2 complex in pure methanol. The structure of this complex, obtained by quantum semi-empirical AM1 method, indicated that complexed 3HF adopts a pyronium form. Structural and electronic modifications induced by chelation are illustrated by the important frequency shifts observed between free and complexed 3HF FT–Raman spectra and by the chemical shifts variations in the 13C NMR spectra of the two species. Complexes with the same stoichiometry were formed when AcO − or MeO − are present in the medium. However, in acidic medium the chelate composition is Al 2(3HF).