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.
- Schiff bases
- Alkali and alkaline earth metal salts
- Molecular spectroscopy
- X-ray crystallography
Kamounah, F. S., Deneva, V., Manolova, Y., Lubenov, L., Kuteva, V., Nikolova, R., & Shivachev, B. (2013). Controlled shift in the tautomeric equilibrium of 4-((phenylimino)methyl)naphthalen-1-ol. Journal of Molecular Structure: THEOCHEM, 1036(2013), 267-273. . https://doi.org/10.1016/j.molstruc.2012.11.055