Tautomeric equilibria for ionized oxamic acid - inhibitor of LDH

Authors

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

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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Journal title

volume 4  issue 2

pages  113- 122

publication date 2011-03-31

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