Density functional study of the monocationic hypoxanthine tautomers

摘要

The chemical and physicochemical properties of the purine derivative hypoxanthine have been the subject of study for several year from different points of view. In this article, the density functional theory study of the hypoxanthine monocationic state was carried out; the relative energetic stabilities, the structural parameters, several electronic structure properties, the tautomeric equilibrium constants and the IR vibrational spectra of the first five energetically most stable hypoxanthine tautomers were calculated. Additionally, we obtained the #DELTA#G for certain heterocylic protonic transfer processes. The theoretical properties of the comparatively most stable 179 ketonic tautomer are discussed and successfully employed to analyze some features of the experimental physicochemical and chemical behavior of this hypoxanthine~(1+) predominant tautomer, as inferred from the studies on hypoxanthine-Lewis acid chemical interactions both in solution and in solid state.