Tautomeric equilibria for ionized oxamic acid - inhibitor of LDH
الموضوعات : Journal of the Iranian Chemical ResearchEwa D. Raczyńska 1 , Małgorzata Hallmann 2 , Kinga Duczmal 3
1 - Department of Chemistry, Warsaw University of Life Sciences (SGGW), 02-776 Warszawa, Poland
2 - Department of Chemistry, Warsaw University of Life Sciences (SGGW), 02-776 Warszawa, Poland
3 - Department of Chemistry, Warsaw University of Life Sciences (SGGW), 02-776 Warszawa, Poland
الکلمات المفتاحية: DFT, Oxamic acid, Amide-iminol tautomerism, Ionization, &pi, -electron delocalization,
ملخص المقالة :
Amide-iminol tautomerism was studied for ionized oxamic acid (OA+•) in the gas phase using theDFT method with the UB3LYP functional and various basis sets {6-31++G(d,p), 6-311+G(d,p), and augcc-pVDZ}. Among twenty tautomers-rotamers possible for OA+•, eleven isomers were found to bethermodynamically stable. Similarly as for the neutral molecule, ionization (OA → OA+• + e) favors theamidization process (amide ← iminol). Isomerization seems to change solely the conformationalpreferences. π-Electron delocalization in the NCO and OCO moieties is close to that for n-π conjugatedfragments.
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