Quantum-chemical study of possible structural transformations in 3-methylthio-3-phenyl-2-propenethial
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Abstract
The plausible formation of 3-methylthio-1-phenyl-2-propene-1-thione and 3-methylthio-3-phenyl-2-propenethial in the reaction of 3-methylthio-3-phenyl-2-propene-1-N,N-dimethyliminium iodide with hydrogen sulfide was shown in the framework of semiempirical AM1 and PM3 methods. In polar media, these products can be trimerized into four types of structures. The kind of trimer depends on the shift of the equilibrium in the 3-methylthio-3-phenyl-2-propenethial ⇄ 3-methylthio-1-phenyl-2-propene-1-thione mixture. Each of the four types of trimers is characterized by the presence of three nearly planar sixmembered pseudo-chelate rings. The possibility of obtaining derivatives of 1,2-dithiolane (the basic fragment of lipoic acid) from the reaction products in nonpolar solvents was considered.
Key words
quantum-chemical calculations, AM1 and PM3 methods conformation 3-methylthio-3-phenyl-2-propenethial, trimerization, dithiolane, solvent polarityPreview
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References
- 1.L. V. Timokhina, G. M. Panova, and M. G. Voronkov,Tez. dokl. 19-i Vseros. konf. po khimii and tekhnologii organ soed. sery [Abstr. 19th All-Russ. Conf. on Chem. and Technol. of Org. Compds. of Sulfur], Kazan' (Russian), 1995, 11 (in Russian).Google Scholar
- 2.M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart,J. Am. Chem. Soc., 1985,107, 3902.CrossRefGoogle Scholar
- 3.M. J. S. Dewar and E. G. Zoebisch,J. Mol. Struct., 1988,180, 1.CrossRefGoogle Scholar
- 4.J. J. P. Stewart,J. Comput. Chem., 1989,10, 209.CrossRefGoogle Scholar
- 5.G. E. Chudinov, D. V. Napolov, and M. V. Basilevsky,Chem. Phys., 1992,160, 41.CrossRefGoogle Scholar
- 6.M. V. Bazilevsky, G. E. Chudinov, and D. V. Napolov,Khim. Fiz., 1992,11, 691 [Sov. Chem. Phys., 1992,11 (Engl. Transl.)].Google Scholar
- 7.M. V. Basilevsky, G. E. Chudinov, D. V. Napolov, and L. M. Timofeeva,Chem. Phys., 1993,173, 345.CrossRefGoogle Scholar
- 8.J. L. Kice, inSulfur in Organic and Inorganic Chemistry, Ed. A. Senning, Dekker, New York, 1971,1, Ch. 6.Google Scholar
- 9.G. Bergson,Ark. Kemi., 1962,19, 265;Chem. Abstrs., 1963,58, 3292.Google Scholar
- 10.A. L. Fluharty inThe Chemistry of the Thiol Group, Part 2, Ed. S. Patai, Interscience, London, 1974, Ch. 13.Google Scholar
- 11.L. J. Reed, inComprehensive Biochemistry, Eds. M. Florkin and E. N. Stotz, Elsevier, Amsterdam, 1966,14, 99.Google Scholar