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ПРИКЛАДНАЯ ХИМИЯ И ХИМИЧЕСКАЯ ТЕХНОЛОГИЯ
УДК 547-386
E. S. Titova, V. A. Babkin, G. E. Zaikov, O. Yu. Emelina, L. M. Lisina
THE PROOF OF FORMATION S-SODIUM SALT OF 6-METHYL-2-THIOURACIL
Keywords: 6-methyl-2-thiouracil, infrared and proton magnetic resonance spectroscopy
The formation of S-sodium salt of 6-methyl-2-thiouracil was proof by the methods of infrared and proton magnetic resonance spectroscopy.
Ключевые слова: 6-метил-2-тиоурацил, инфракрасная и протонная магнитно-резонансная спектроскопии.
Формирование S-натриевой соли 6-метил-2-тиоурацила доказывалось с помощью методов инфракрасной и протонной магнитно-резонансной спектроскопий
Aims and backgrounds
The synthesis of S -monoderivatives of 6-methyl-2-thiouracil by the reaction of the nucleophilic substitution in halogenated hydrocarbons proceeds through the phase of the formation of the sodium salt of S-6-methyl-2-thiouracil. It was interesting to prove the formation of the sodium salt [1-8].
Methodology
The molecule of 6-methyl-2-thiouracil exists in two tautomeric forms: oxo-thio and hydroxo- mercapto. The keto form of 2-thiouracils is the most stable.
For the dissolving of 6-methyl-2-thiouracil it is necessary to convert it from the oxo-thione form into the oxo-mercapto form. We used the equimolar relations of 6-methyl-2-thiouracil and sodium hydroxide. Where in the tautomeric transformations occurred with the participation of the sulfur atom of thiouracil only.
Resultats of the investigation
Under the action of an aqueous solution of sodium hydroxide on 6-methyl-2-thiouracil (fig. 1) the formation of the water-soluble S- sodium salt takes place.
CH
дмсо
Jll
CH3
ГМДС
7 6 5 4 3 2 ppm
NH
14 13 12 11 10 9
Fig. 1 - PMR-range of 6-methyl-2-thiouracil
The structure and composition of the S-sodium salt of 2-thiol-6-methylpyrimidin-4 (3H)-on was proved by the IR, PMR-spectroscopy (fig.2-3) and by the facts of the elementary nitrogen analysis.
There is no signal in the PMR spectrum of the salt in the 2.3 m.d. which is characterized for the NH-group, located in the position of the 1 heterocycle of 6-methyl-2-thiouracil.
p
HO
NH( 3 nojioMceHHe)
CH
(5nojio2Keime)
AMCO
J V
CH3
TM^C
Fig. 2 - PMR-range of S-sodium salt of 2-thiol-6-methylpyrimidin-4 (3H)-on
100
60
20
0
4 4- 1H \ifi
ffV^ ¡¡ftohW -4 | FF
/ 4--
Hi
4000 3400 2S00 2200 1600 1000
Fig. 3 - IR-range of S-sodium salt of 2-thiol-6-methylpyrimidin-4 (3H)-on
Conclusion
Thus, during the reaction of 6-methyl-2-thiouracil with the equimolar amount of sodium hydroxide the S-sodium salt is formed. Further the thioanion is generated in the aquatic-dioxane medium [9-12]. The resulting anion reacts with an equimolar amount of the halogeno by the mechanism of the nucleophilic substitution with the formation of S-monoderivatives of 6-methyl-2-thiouracil only.
References
1. Titova E.S. The thesis for the degree of Candidate of Sciences / Volgograd, 2005. pp.214
2. Rakhimov A.I, Titova E.S. The patent on invention. RUS 231141211.07.2006.
3. Rakhimov A.I, Popov V., Titova E.S. Proceedings of the Volgograd State Technical University. 2005. № 1. pp. 61 -64.
4. Rakhimov A.I, Titova E.S. The Journal of General Chemistry. 2007. T. 43. № 1. pp. 92-98.
5. Rakhimov A.I, Titova E.S. Proceedings of the Volgograd State Technical University. 2006. № 1. pp. 66 - 72.
6. Rakhimov A.I, Titova E.S, Fedunov R.G, Babkin V.A. Chemistry of Heterocyclic Compounds.Riga. 2008. № 6. Pp. 874-883.
7. Babkin V.A, Rakhimov A.I, Titova E.S, Fedunov R.G., RESHETNIKOV R.A, BELOUSOVA V.S, ZAIKOV G.E. Chemical Physics and Mesoscopy.Igevsk. 2007. T. 9. № 3. pp. 263-275.
8. Rakhimov A.I., Titova E.S. Russian Journal of Organic Chemistry. 2007. r 43. № 1. pp. 96-102.
9. Rakhimov A.I, Titova E.S., Fedunov R.G., Babkin V.A., Belousova V.S., Rusanova S.N., Zaikov G.E. / / Herald of the Kazan State Technological University. - 2013. - T. 16, № 5. - pp. 16-20.
10. Rakhimov A.I, Titova E.S, Fedunov R.G, Babkin V.A, Stoyanov O.V., Zaikov G.E. Herald of the Kazan State Technological University. - 2013. - T. 16, № 5. - pp. 23-29.
11. Rakhimov A.I., Titova E.S., Fedunov R.G., Babkin V.A. Proceedings of the Volgograd State Technical University. 2008.T. 1. № 5. pp. 70 - 76.
12. Rakhimov A.I., Babkin V.A., Titova E.S., Fedunov R.G., Belousova V.S., Zaikov G.E. In the collection: The Theoretical and Applied Aspects of Quantum-chemical Calculations of Molecular Systems. The Unique Collection Articles: a 59-th Anniversary of the Professor Babkin V. A. V.A. Volgograd, 2011. Pp. 41-50.
© E. S. Titova - assistant professor, Volgograd State Technical University, Volgograd, Russian Federation; V. A. Babkin - professor, Volgograd State University of Architecture and Civil Engineering, Sebryakovsky branch, Mikhailovka, Russian Federation, [email protected]; G. E. Zaikov - professor, Department of technology of plastic materials, Kazan National Research Technological University, Kazan, Russian Federation; O. Yu. Emelina - assistant, Department of technology of plastic materials, Kazan National Research Technological University, Kazan, Russian Federation; L. M. Lisina - assistant professor, Volgograd State University of Architecture and Civil Engineering, Sebryakovsky branch, Mikhailovka, Russian Federation.
© Е. С. Титова - доцент, Волгоградский государственный технический университет, Волгоград, Российская Федерация; В. А. Бабкин - профессор, Себряковский филиал Волгоградского государственного архитектурно-строительного университета, [email protected]; Г. Е. Заиков - профессор каф. технологии пластических масс КНИТУ; О. Ю. Емелина -ассистент той же кафедры; Л. М. Лисина - доцент, Себряковский филиал Волгоградского государственного архитектурно-строительного университета.
