Catalytic Action of Water during Nucleophilic Substitution of Halogen in Hexachlorocyclotriphosphazatriene with Pyridine N-Oxide
- 6 Downloads
The data on the kinetics of the reaction between hexachlorocyclotriphosphazatriene (the phosphazene) with pyridine N-oxide in mixed organic solvents in the presence of water are presented. The reaction of the phosphazene with pyridine N-oxide leads to the formation of the onium salt. It has been found that water catalyzes this reaction, the catalytic action resulting from the solvation of the polar transition state due to the formation of the phosphazene complex with hydrogen bonding, thus facilitating the rupture of the phosphorus bond with the leaving anion.
Keywordsphosphazene hexachlorocyclotriphosphazatriene pyridine N-oxide nucleophilic substitution of halogen
Unable to display preview. Download preview PDF.
This study was financially supported by the Ministry of Education and Science of the Russian Federation (RFMEFI57717X0264).
- 1.Allcock, H.R., Phosphorus Nitrogen Compounds, New York: Academic Press Inc., 1972.Google Scholar
- 2.Titskii, G.D., Shumeiko, A.E., Kurchenko, L.P., Popov, A.F., Vapirov, V.V., Afon’kin, A.A., and Turovskaya, M.K., Author’s Certificate 1391064, 1986; Byull. Izobret., 1999, no. 6.Google Scholar
- 3.Yang M, Talke, F.E., Perettie, D.J., Morgan, T.A., and Kar, K.K., IEEE Trans. Mag., 1994, p. 4143. doi 10.1109/20.334016Google Scholar
- 8.Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Мoscow: Novaya Volna, 2002.Google Scholar
- 9.Terekhov, I.V., Filatov, S.N., Orlov, A.I., Savel’eva, A.V., and Zauzina E.A., Usp. Khim. Khim. Tekhnol., 2013, vol. 27, no. 3, p. 112.Google Scholar
- 10.Tupikov, A.S., Chistyakov, E.M., and Kireev, V.V., Usp. Khim. Khim. Tekhnol., 2012, vol. 26, no. 4, p. 114.Google Scholar
- 11.Terekhov, I.V., Chistyakov, E.M., Filatov, S.N., Dernovaya, E.S., and Zauzina, E.A., Usp. Khim. Khim. Tekhnol., 2012, vol. 26, no. 4, p. 106.Google Scholar
- 16.Vapirov, V.V., Tunina, S.G., and Ryzhakov, A.V., Russ. J. Gen. Chem., 1994, vol. 64, no. 2, p. 273.Google Scholar
- 17.Vapirov, V.V. Doctoral Sci. (Chem.) Dissertation, St. Petersburg, 2000.Google Scholar
- 18.Svoistva organicheskikh soedinenii (Properties of Organic Compounds), Potekhin, A.A., Ed., Leningrad: Khimiya, 1984.Google Scholar
- 19.Metody polucheniya khimicheskikh reaktivov i preparatov (Methods of Obtaining Chemical Reagents and Preparations), Moscow: IREA, 1962, nos. 4–5, p. 59.Google Scholar
- 20.Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques and References, New York: Wiley, 1972.Google Scholar