Controlled shift in the tautomeric equilibrium of 4-​((phenylimino)​methyl)​naphthalen-​1-​ol

Fadhil S. Kamounah, V Deneva, y Manolova, L Lubenov, V Kuteva, R Nikolova, B Shivachev

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    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.
    TidsskriftJournal of Molecular Structure: THEOCHEM
    Udgave nummer2013
    Sider (fra-til)267-273
    Antal sider7
    StatusUdgivet - 2013


    • Tautomerism
    • Schiff bases
    • Alkali and alkaline earth metal salts
    • Molecular spectroscopy
    • X-ray crystallography

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