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Collect. Czech. Chem. Commun. 2009, 74, 57-72
https://doi.org/10.1135/cccc2008149
Published online 2009-01-22 17:12:05

Stability, polarity, intramolecular interactions and π-electron delocalization for all eighteen tautomers rotamers of uracil. DFT studies in the gas phase

Ewa D. Raczyńskaa,*, Katarzyna Zientarab, Tomasz M. Stępniewskib and Katarzyna Kolczyńskab

a Department of Chemistry, Warsaw University of Life Sciences, 02-776 Warszaw, Poland
b Interdisciplinary Department of Biotechnology, Warsaw University of Life Sciences, 02-726 Warsaw, Poland

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  • El-Demerdash Safinaz H., Gad Shaimaa F.: A computational study of gas-phase acidity and basicity of azulene-based uracil analogue. Struct Chem 2020, 31, 319. <https://doi.org/10.1007/s11224-019-01408-8>
  • Raczyńska Ewa D., Juras Weronika: Effects of ionization and proton-transfer on bond length alternation in favored and rare isomers of isocytosine. Computational and Theoretical Chemistry 2019, 1148, 16. <https://doi.org/10.1016/j.comptc.2018.12.010>
  • Gad Shaimaa F., El-Demerdash Safinaz H., El-Mehasseb Ibrahim M., El-Nahas Ahmed M.: Structure, stability and conversions of tautomers and rotamers of azulene-based uracil analogue. Journal of Molecular Structure 2019, 1182, 271. <https://doi.org/10.1016/j.molstruc.2019.01.020>
  • Zhang Jian, Li Xiu: The effect of water-mediated catalysis on the intramolecular proton-transfer reactions of the isomers of 5-chlorouracil: a theoretical study. Acta Crystallogr C Struct Chem 2019, 75, 554. <https://doi.org/10.1107/S2053229619004856>
  • Raczyńska Ewa D.: Application of the Extended HOMED (Harmonic Oscillator Model of Aromaticity) Index to Simple and Tautomeric Five-Membered Heteroaromatic Cycles with C, N, O, P, and S Atoms. Symmetry 2019, 11, 146. <https://doi.org/10.3390/sym11020146>
  • Raczyńska Ewa D., Makowski Mariusz: Effects of Positive and Negative Ionization on Prototropy in Pyrimidine Bases: An Unusual Case of Isocytosine. J. Phys. Chem. A 2018, 122, 7863. <https://doi.org/10.1021/acs.jpca.8b07539>
  • Li Dejie, Han Ying, Li Huijuan, Zhang Ping, Kang Qi, Li Zhihua, Shen Dazhong: The influence of isolated and penta-hydrated Zn2+ on some of the intramolecular proton-transfer processes of thymine: a quantum chemical study. RSC Adv. 2018, 8, 11021. <https://doi.org/10.1039/C7RA13750H>
  • Raczyńska Ewa D.: Quantum-chemical studies on the favored and rare isomers of isocytosine. Computational and Theoretical Chemistry 2017, 1121, 58. <https://doi.org/10.1016/j.comptc.2017.10.007>
  • Udagawa Taro: Theoretical analysis on the aromaticity of uracil: Important electronic configurations and solvent effect on the aromaticity. Chemical Physics Letters 2015, 637, 115. <https://doi.org/10.1016/j.cplett.2015.07.057>
  • Raczyńska Ewa D.: Electron delocalization and relative stabilities for the favored and rare tautomers of hydroxyazines in the gas phase – A comparison with aminoazines. Computational and Theoretical Chemistry 2014, 1042, 8. <https://doi.org/10.1016/j.comptc.2014.04.015>
  • Krygowski Tadeusz M., Szatylowicz Halina, Stasyuk Olga A., Dominikowska Justyna, Palusiak Marcin: Aromaticity from the Viewpoint of Molecular Geometry: Application to Planar Systems. Chem. Rev. 2014, 114, 6383. <https://doi.org/10.1021/cr400252h>
  • Stasyuk Olga A., Szatylowicz Halina, Krygowski Tadeusz M.: Tautomerisation of thymine acts against the Hückel 4N + 2 rule. The effect of metal ions and H-bond complexations on the electronic structure of thymine. Org. Biomol. Chem. 2014, 12, 6476. <https://doi.org/10.1039/C4OB00964A>
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  • Raczyńska Ewa D., Hallman Małgorzata, Kolczyńska Katarzyna, Stępniewski Tomasz M.: On the Harmonic Oscillator Model of Electron Delocalization (HOMED) Index and its Application to Heteroatomic π-Electron Systems. Symmetry 2010, 2, 1485. <https://doi.org/10.3390/sym2031485>