EXPERIMENTAL AND QUANTUM-CHEMICAL STUDY OF THE MECHANISM OF OXIDATION OF 5-HYDROXY-6-METHYLURACIL BY MOLECULAR OXYGEN IN THE PRESENCE OF COPPER(II) IONS

Authors

  • Ю. И. Муринов Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences
  • Т. Р. Нугуманов Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences
  • С. П. Иванов Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences
  • М. Е. Клецкий Chemical Faculty, Southern Federal University, Rostov-on-Don 344090
  • И. Ф. Камалетдинов Chemical Faculty, Southern Federal University, Rostov-on-Don 344090
  • В. И. Минкин Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don 344090

DOI:

https://doi.org/10.1007/6756

Keywords:

5-hydroxy-6-methyluracil, active forms of oxygen, oxidation with molecular oxygen, quantum-chemical calculations

Abstract

It has been discovered experimentally that 5,5,6-trihydroxy-6-methylpyrimidine-2,4-dione is formed on oxidizing 5-hydroxy-6-methyluracil with molecular oxygen in aqueous medium in the presence of copper(II) chloride. Ab initio and DFT calculations on the 6-31G* basis, both in the gas phase and allowing for solvent, showed that the process proceeds with the direct participation of an activated oxygen molecule on the complex CuCl<sub>2</sub>·(5-hydroxy-6-methyluracil)<sub>2</sub>.

How to Cite
Murinov, Yu. I.; Nugumanov, T. R.; Ivanov, S. P.; Kletskii, M. E.; Kamaletdinov, I. F.; Minkin, V. I.  Chem. Heterocycl. Compd. 2009, 45, 461. [Khim. Geterotsikl. Soedin. 2009, 586.]

For this article in the English edition see DOI 10.1007/s10593-009-0286-7

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Published

2022-04-25

Issue

No. 4 (2009)

Section

Original Papers