Abstract
Previously unknown S-(trimethoxysilylmethyl)- and S-(silatranylmethyl)isothiuronium halides and their N-substituted derivatives were prepared. According to the IR and UV spectra, these compounds exist in the solid state and in methanol and acetonitrile solutions in the form of two equilibrium salt structures: those with the positively charged nitrogen and carbon atoms, or predominantly in one of these. In solutions of the iodides in highly polar acetonitrile, the first salt structure can occur in an equilibrium with its dissociation products, S-organylisothiourea (or its N-substituted derivative) and hydrogen iodide.
Similar content being viewed by others
REFERENCES
Bakhareva, E.V., Pestunovich, A.E., Vlasova, N.N., Vasil'eva, N.N., and Voronkov, M.G., Abstracts of Papers, 4-ya Vsesoyuznaya konferentsiya “Biologicheski aktivnye soedineniya kremniya, germaniya i olova” (4th All-Union Conf. “Biologically Active Compounds of Silicon, Germanium, and Tin”), Irkutsk, 1990, p. 20.
Safaev, R.D., Voronkov, M.G., Fuks, S.Yu., Lycheva, T.A., Khitrova, I.L., Belitskii, G.A., Pakhomov, V.Yu., Vlasova, N.N., and Pestunovich, A.E., Dokl. Ross. Akad. Nauk, 1992, vol. 322,no. 5, p. 994.
Kazimirovskaya, V.B., Pestunovich, A.E., Usov, V.A., Dorofeev, I.A., Vlasova, N.N., and Voronkov, M.G., Abstracts of Papers, 4-ya Vsesoyuznaya konferentsiya “Biologicheski aktivnye soedineniya kremniya, germaniya i olova” (4th All-Union Conf. “Biologically Active Compounds of Silicon, Germanium, and Tin”), Irkutsk, 1990, p. 23.
Voronkov, M.G., Vlasova, N.N., and Pozhidaev, Yu.N., Zh. Prikl. Khim., 1996, vol. 69,no. 5, p. 705.
Voronkov, M.G., Vlasova, N.N., and Pozhidaev, Y.N., Appl. Organomet. Chem., 2000, vol. 14,no. 6, p. 287.
US Patent 3 637 735, 1972, Chem. Abstr., 1972, vol. 76, 85 915u; US Patent 3 780 175, 1973, Chem. Abstr., 1974, vol. 80, 60 027a; Ref. Zh. Khim., 1974, 23N322P.
Voronkov, M.G., Sorokin, M.S., D'yakov, V.M., and Sigalov, M.V., Zh. Obshch. Khim., 1975, vol. 45,no. 8, p. 1807.
Voronkov, M.G. and Sorokin, M.S., Zh. Obshch. Khim., 1979, vol. 49,no. 12, p. 2671.
Voronkov, M.G., Sorokin, M.S., and D'yakov, V.M., Zh. Obshch. Khim., 1979, vol. 49,no. 3, p. 605.
Voronkov, M.G. and Sorokin, M.S., Zh. Obshch. Khim., 1986, vol. 56,no. 5, p. 1098.
Voronkov, M.G. and Sorokin, M.S., Zh. Obshch. Khim., 1979, vol. 49,no. 12, p. 2671.
Salman, S.R., Lindon, J.C., Farrant, R.D., and Carpenter, T.A., Magn. Reson. Chem., 1993, vol. 31, p. 991.
Nakanishi, K., Infrared Absorption Spectroscopy, Tokyo: Nankido, 1962.
Bellamy, L.J., Advances in Infrared Group Frequencies, London: Methuen, 1968.
Stern, E.S. and Timmons, C.J., Gillam and Stern's Introduction to Electronic Absorption Spectroscopy in Organic Chemistry, London: Edward Arnold, 1970.
Gordon, A.J. and Ford, R.A., The Chemist's Companion. A Handbook of Practical Data, Techniques, and References, New York: Wiley, 1972.
D'yakov, V.M., Lukina, Yu.A., Voronkov, M.G., Gubanova, L.I., Samsonova, G.A., and Tandura, S.N., Izv. Akad. Nauk SSSR, Ser. Khim., 1978, no. 10, p. 2366; Voronkov, M.G., D'yakov, V.M., and Gubanova, L.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1974, no. 3, p. 657.
Voronkov, M.G., D'yakov, V.M., Lukina, Yu.A., Samsonova, G.A., and Kudyakov, N.M., Zh. Obshch. Khim., 1975, vol. 45,no. 9, p. 2010.
Voronkov, M.G., D'yakov, V.M., Samsonova, G.A., Lukina, Yu.A., and Kudyakov, N.M., Izv. Akad. Nauk SSSR, Ser. Khim., 1974, no. 12, p. 2794.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sorokin, M.S., Lopyrev, V.A., Chipanina, N.N. et al. S-(Trimethoxysilylmethyl)- and S-(Silatranylmethyl)isothiuronium Halides and Their N-Substituted Derivatives. Russian Journal of General Chemistry 74, 551–558 (2004). https://doi.org/10.1023/B:RUGC.0000031856.58701.2c
Issue Date:
DOI: https://doi.org/10.1023/B:RUGC.0000031856.58701.2c