International Journal of
Physical Sciences

  • Abbreviation: Int. J. Phys. Sci.
  • Language: English
  • ISSN: 1992-1950
  • DOI: 10.5897/IJPS
  • Start Year: 2006
  • Published Articles: 2557

Full Length Research Paper

DFT study of solvent effects on tautomerization of 4-(2-thiazolylazo)-resorcinol

S. Ali Beyramabadi*,  Mohammad Reza Bozorgmehr and  Ali Morsali     :   
Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran.  
Email: [email protected]

  •  Accepted: 06 September 2011
  •  Published: 16 October 2011


Here, the structural parameters of the enol and keto tautomers of the 4-(2-thiazolylazo)-resorcinol (TAR) were determinate. Also, tautomerization mechanism of the TAR was investigated, employing density functional theory and the polarizable continuum model (PCM). In addition to the gas phase calculations, the tautomerization mechanism of the TAR was investigated in the chloroform and dimethyl sulfoxide (DMSO) solutions for analysis of the solvent effects. More polar solvent results in higher activation energy for the keto-enol tautomerization, and larger amount of keto tautomer than the enol.


Key words: Density functional theory (DFT), 4-(2-thiazolylazo)-resorcinol, enol-keto tautomerism, polarizable continuum model (PCM), mechanism, solvent effects.