Abstract
Protonation of triethyl (2-pyridylimido)phosphates has been studied by potentiometric titration in nitromethane, IR and NMR spectroscopy, and X-ray structure analysis. The substances studied are protonated in one step at the N-atom of the pyridine ring. The protonated cations may be represented, according to the X-ray data, as a resonance of two structures: pyridinium and pyridoniminium; the contribution of the latter probably being considerable. Changes in spectral parameters of POEt groups upon protonation of pyridylimidophosphates (PIP) have been noted.
Similar content being viewed by others
References
E.I.Matrosov, R.U.Amanov, M.Yu.Antipin, Yu.T.Struchkov, A.A.Khodak, A.G.Matveeva, and M.I. Kabachnik,Dokl.Akad.Nauk SSSR, 1991,316, 161 [Dokl.Chem. (Engl.Transl.)].
G.K.Genkina, B.A.Korolev, V.A.Gilyarov, and M.I.Kabachnik,Zh.Obshch.Khimii, 1978,41, 80 [J.Gen. Chem. USSR (Engl.Transl.)].
M.Yu.Antipin, Yu.T.Struchkov, N.A.Tikhonina, V.A.Gilyarov, and M.I.Kabachnik,Zh.Struktur.Khimii, 1981, 93 [J.Struct. Chem., (Engl.Transl.)].
A.W.Schuester and C.I.Jocobson,J.Chem.Soc.A., 1968, 2317.
A.N.Cherenga, A.A.Korkin, M.Yu.Antipin, and Yu.T.Struchkov,Zh.Obshch.Khimii, 1988,9, 2045 [J.Gen. Chem. USSR, (Engl.Transl.)].
E.I.Matrosov, A.G.Kozachenko, and M.I. Kabachnik,Izv.Akad.Nauk SSSR, Ser.Khim., 1976, 1470 [Bull.Acad.Sci. USSR. Div.Chem.Sci., 1976,25, No.7].
Fizicheskie Metody v Khimii Geterotsiklicheskikh Soedinenii. Ed. A.P.Katritsky, Khimiya, Moscow, Leningrad, 1966, 658.
L.L.Bellami,The Infra-Red Spectra of Complex Molecules, Wiley, London, Metluen, New York, 1963.
E.I.Matrosov, A.G.Matveeva, G.V.Bodrin, B.K.Shcherbakov, Yu.M.Polikarpov, and M.I.Kabachnik,Izv.Akad.Nauk SSSR, Ser.Khim., 1991, 922 [Bull.Acad.Sci.USSR.Div.Chem.Sci., 1991,40, 818].
H.R.Hudson,Quasi-Phosphonium Intermediates and Compounds, inTopics in Phosphorus Chemistry,11, 339.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No 1, pp. 88–91, January, 1993.
Rights and permissions
About this article
Cite this article
Amanov, R.U., Matrosov, E.I., Antipin, M.Y. et al. Protonation of triethyl (2-pyridylimido)phosphates. Russ Chem Bull 42, 77–81 (1993). https://doi.org/10.1007/BF00699979
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00699979