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Protonation of 1,2,4-triazine 4-oxides

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Abstract

The basicity of some 1,2,4-triazine 4-oxides was estimated on a quantitative level, and their probable protonation patterns were ascertained. The dissociation constants of mono- and diprotonated 3-R-6-phenyl-1,2,4-triazine 4-oxides in aqueous buffer solutions and aqueous sulfuric acid solutions were determined (6-phenyl-1,2,4-triazine 4-oxide: \(pK_{BH^ + } = 1.1\), \(pK_{BH^{2 + } } = - 6.02\)). According to the results of DFT calculations (B3LYP/6-311**) and spectral data, first protonation of 1,2,4-triazine 4-oxides involves the N1 nitrogen atom, and the second proton adds to the N-oxide oxygen atom.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    R. E. Trifonov & V. A. Ostrovskii

  2. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    R. E. Trifonov

  3. Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, ul. Akademicheskaya/S. Kovalevskoi 22/20, Yekaterinburg, 620990, Russia

    V. L. Rusinov & O. N. Chupakhin

Authors
  1. R. E. Trifonov
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  2. V. A. Ostrovskii
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  3. V. L. Rusinov
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  4. O. N. Chupakhin
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Correspondence to R. E. Trifonov.

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Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on her jubilee

Original Russian Text © R.E. Trifonov, V.A. Ostrovskii, V.L. Rusinov, O.N. Chupakhin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 3, pp. 462–466.

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Trifonov, R.E., Ostrovskii, V.A., Rusinov, V.L. et al. Protonation of 1,2,4-triazine 4-oxides. Russ J Org Chem 49, 450–454 (2013). https://doi.org/10.1134/S1070428013030238

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  • DOI: https://doi.org/10.1134/S1070428013030238

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