TAUTOMERIZATION OF PYRIDO[2Вў,1Вў:2,3]IMIDAZO [4,5-b]QUINOLINE-12-YLCYANIDE: A DFT STUDY
S. A. Beyramabadi, A. Morsali, M. Pordel, H. Chegini, M. Khashi, I. Ahmadi, M. Poorzaki
Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran
beiramabadi@yahoo.com. beiramabadi6285@mshdiau.ac.ir
Keywords: DFT, PCM, intramolecular proton transfer, AIM analysis, tautomerization
Abstract
The titled imidazo compound can exist as three tautomers: OH, CH, and NH forms. Firstly, the OH tautomer is produced, which can be tautomerized to the CH and NH tautomers via the intramolecular-proton transfer. Herein, employing density functional theory and handling the solvent effects with the PCM model, the structural parameters, energy behavior, and also tautomerization mechanism of the tautomers are investigated. Based on the DFT results and the obtained-AIM parameters, the CH tautomer is considered to be the most stable one. Also, the CH tautomer is a kinetically and thermodynamically controlled product in tautomerization of the OH tautomer in a methanol solution.
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