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

    Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

    Abstract

    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.
    OriginalsprogEngelsk
    Artikelnummer2
    TidsskriftJournal of Molecular Structure: THEOCHEM
    Vol/bind1036
    Udgave nummer2013
    Sider (fra-til)267-273
    Antal sider7
    ISSN0166-1280
    DOI
    StatusUdgivet - 2013

    Emneord

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

    Citer dette

    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. [2]. https://doi.org/10.1016/j.molstruc.2012.11.055