Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects
Само за регистроване кориснике
2024
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Computational investigationattheBHandHLYP/6-311+G(d,p) leveloftheoryofthegas-phasetautomerismof2-and4-pyridonesconfirmedtheslightprevalenceof lactiminthecaseof theformer,but its dominance inthecaseof the latter, asshownpreviously. Examinationof aromaticitybyusingHOMA, EDDB, NBOdel, NICSandAICD led to theconclusion that tautomerizationof 4-pyridone results in greateraromaticitygain. ItisalsodrivenbythePaulirepulsionrelief,whichwasrevealedbythetautomerizationenergydecompositionanalysis.Bycontrast, inthecaseof2-pyridone, lactimisfavouredbyorbital andelectrostatic interactions anddisfavouredby thePauli repulsion. Aromaticitygain in this case is smaller.Thepositionofthetautomericequilibriumcanbemodulatedbysubstituent inductiveeffects(Cl andF), inductiveandresonanceeffects (NH2andNO2),hydrogenbonding(NO2),andmediumpolarity, theincreaseofwhichincreaseslactampopulation.
Извор:
Organic & Biomolecular Chemistry, 2024, 22, 1, 144-158Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-MESTD-inst-2020-200168)
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Baranac-Stojanović, Marija AU - Aleksić, Jovana AU - Stojanović, Milovan PY - 2024 UR - http://cherry.chem.bg.ac.rs/handle/123456789/6417 AB - Computational investigationattheBHandHLYP/6-311+G(d,p) leveloftheoryofthegas-phasetautomerismof2-and4-pyridonesconfirmedtheslightprevalenceof lactiminthecaseof theformer,but its dominance inthecaseof the latter, asshownpreviously. Examinationof aromaticitybyusingHOMA, EDDB, NBOdel, NICSandAICD led to theconclusion that tautomerizationof 4-pyridone results in greateraromaticitygain. ItisalsodrivenbythePaulirepulsionrelief,whichwasrevealedbythetautomerizationenergydecompositionanalysis.Bycontrast, inthecaseof2-pyridone, lactimisfavouredbyorbital andelectrostatic interactions anddisfavouredby thePauli repulsion. Aromaticitygain in this case is smaller.Thepositionofthetautomericequilibriumcanbemodulatedbysubstituent inductiveeffects(Cl andF), inductiveandresonanceeffects (NH2andNO2),hydrogenbonding(NO2),andmediumpolarity, theincreaseofwhichincreaseslactampopulation. T2 - Organic & Biomolecular Chemistry T1 - Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects VL - 22 IS - 1 SP - 144 EP - 158 DO - 10.1039/D3OB01588B ER -
@article{ author = "Baranac-Stojanović, Marija and Aleksić, Jovana and Stojanović, Milovan", year = "2024", abstract = "Computational investigationattheBHandHLYP/6-311+G(d,p) leveloftheoryofthegas-phasetautomerismof2-and4-pyridonesconfirmedtheslightprevalenceof lactiminthecaseof theformer,but its dominance inthecaseof the latter, asshownpreviously. Examinationof aromaticitybyusingHOMA, EDDB, NBOdel, NICSandAICD led to theconclusion that tautomerizationof 4-pyridone results in greateraromaticitygain. ItisalsodrivenbythePaulirepulsionrelief,whichwasrevealedbythetautomerizationenergydecompositionanalysis.Bycontrast, inthecaseof2-pyridone, lactimisfavouredbyorbital andelectrostatic interactions anddisfavouredby thePauli repulsion. Aromaticitygain in this case is smaller.Thepositionofthetautomericequilibriumcanbemodulatedbysubstituent inductiveeffects(Cl andF), inductiveandresonanceeffects (NH2andNO2),hydrogenbonding(NO2),andmediumpolarity, theincreaseofwhichincreaseslactampopulation.", journal = "Organic & Biomolecular Chemistry", title = "Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects", volume = "22", number = "1", pages = "144-158", doi = "10.1039/D3OB01588B" }
Baranac-Stojanović, M., Aleksić, J.,& Stojanović, M.. (2024). Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects. in Organic & Biomolecular Chemistry, 22(1), 144-158. https://doi.org/10.1039/D3OB01588B
Baranac-Stojanović M, Aleksić J, Stojanović M. Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects. in Organic & Biomolecular Chemistry. 2024;22(1):144-158. doi:10.1039/D3OB01588B .
Baranac-Stojanović, Marija, Aleksić, Jovana, Stojanović, Milovan, "Theoretical investigation of tautomerism of 2- and 4-pyridones: origin, substituent and solvent effects" in Organic & Biomolecular Chemistry, 22, no. 1 (2024):144-158, https://doi.org/10.1039/D3OB01588B . .