| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1406139 | Journal of Molecular Structure | 2013 | 7 Pages |
4-((Phenylimino)methyl)naphthalen-1-ol and 4-((phenylimino)methyl)-2-(piperidin-1-ylmethyl)naphthalen-1-ol have been synthesized and their tautomeric properties were investigated using molecular spectroscopy (UV–Vis absorption/emission and NMR), X-ray crystallographic analysis and quantum-chemical calculations. The results show that with the implementation of a flexible piperidine ring a controlled shift in the tautomeric equilibrium will be achieved upon protonation/deprotonation in acetonitrile. The addition of a metal salt also shifts the tautomeric equilibrium, but at very high concentrations, which is caused not by a complex formation, but a special effect of the salt addition.
► 4-((Phenylimino)methyl)-2-(piperidin-1-ylmethyl)naphthalen-1-ol was studied. ► The controlled shift of the tautomeric equilibrium through structural modifications was achieved. ► The inclusion of the piperidine ring leads to shift of the equilibrium to the enol tautomer. ► Upon protonation the equilibrium shifts to the keto tautomer in a controlled and reversible manner. ► The salt addition leads to shift in the tautomeric equilibrium, independly on the kind of salt used.
