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  • Chem Sci Trans., 2013, 2(4),  pp 1370-1378  

    DOI:10.7598/cst2013.448

    Research Article

    A DFT Study on Tautomer Stability of 4-Hydroxyquinoline Considering Solvent Effect and NBO Analysis

  • ZABIALAH HEIDARNEZHAD, FATEMEH HEIDARNEZHAD, IZATULLO GANIEV and ZIYODULLO OBIDOV
  • Department of Chemistry, Islamic Azad University, Andimeshk , Iran
    Chemistry Institute, Tajikistan Academy of Sciences, Dushanbe, Tajikistan
  • Abstract

    Computational calculations at B3LYP/6-311++G (d,p) level were employed in the study of the predominant tautomeric of 4-hydroxyquinoline derivatives (5-H, 5-NO2, 5-Cl, 5-OH, 5-CH3, 6-NO2, 6-Cl, 6-OH, 6-CH3, 7-NO2, 7-Cl, 7-OH, 7-CH3, 8-NO2, 8-Cl, 8-OH, 8-CH3) in the gas phase and selected solvents (benzene (non-polar solvent), tetrahydrofuran (THF) (polar aprotic solvent) and water (protic solvent)). The tautomers were also optimized in solvents according to the polarisable continuum method (PCM). For electron withdrawing and releasing derivatives the order of stability is X1 >X2 >X3 and X1 form is a more stable and dominant form. An exception in the gas phase is X2 isomer of (8-OH) which has two forms. In one, the hydrogen bond between hydroxyl substituted with nitrogen isnít formed, but in another it is formed. If the hydrogen bond is formed, X2 isomer is more stable than X1. In addition variation of dipole moments and charges on atoms in the solvents are studied.

    Keywords

    DFT study, NBO analysis, PCM model, 4-Hydroxyquinoline, Tautomerism

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