Systematic investigation of 2,7-dihydroxy-1,8-naphthyridine dimerization - secondary interactions and tautomeric preferences calculations

The tautomeric preferences and dimer formation of 2,7-dihydroxy-1,8-naphthyridine have been investigated using MP2/6-31G(2d,p), M05/6-311+G(2d,p) and B3LYP/6-311+G(2d,p) computational methods. Both geometrical parameters and energetic data are indicative of the presence of secondary interaction (SI) in the dimer formation. Weak hydrogen bonds (HB) form a cooperative network of SI, while stronger hydrogen bonds compete. The magnitude of the secondary interactions are compared across all dimers. The influence of dimerization on geometry, energy and relative molecules position is discussed.