Abstract
Quantum chemical calculations for 2-oxo-, 2-thioxo-, and 2-selenoxopyrimidin-4-ones, as well as for 5,6-dimethyl-2-oxo- and 5,6-dimethyl-2-thioxothieno[2,3-d]pyrimidin-4-ones, were carried out at the HF and DFT levels. An analysis of the relative energies shows that the 2-oxo form or the related thioxo or selenoxo forms are energetically more favorable in tautomeric interconversions of all the compounds under study both in the gas phase and in solutions in ethanol, acetonitrile, and DMSO.
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For Part 2, see Ref. 1.
On the occasion of the 80th anniversary of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0350–0354, February, 2014.
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Mamarakhmonov, M.K., Belen’kii, L.I., Chuvylkin, N.D. et al. Quantum chemical studies of pyrimidin-4-ones 3. 2-Oxo(thioxo, selenoxo)pyrimidin-4-ones and 5,6-dimethyl-2-oxo(thioxo)thieno[2,3-d]pyrimidin-4-ones. Russ Chem Bull 63, 350–354 (2014). https://doi.org/10.1007/s11172-014-0436-7
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DOI: https://doi.org/10.1007/s11172-014-0436-7