Tautomeric equilibria for ionized oxamic acid - inhibitor of LDH

الموضوعات : Journal of the Iranian Chemical Research

Ewa D. Raczyńska ¹ (Department of Chemistry, Warsaw University of Life Sciences (SGGW), 02-776 Warszawa, Poland)
Małgorzata Hallmann ² (Department of Chemistry, Warsaw University of Life Sciences (SGGW), 02-776 Warszawa, Poland)
Kinga Duczmal ³ (Department of Chemistry, Warsaw University of Life Sciences (SGGW), 02-776 Warszawa, Poland)

تاريخ الإرسال : 23 السبت , ربيع الأول, 1432 تاريخ التأكيد : 07 السبت , ربيع الثاني, 1432 تاريخ الإصدار : 26 الخميس , ربيع الثاني, 1432

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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