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Protolytic equilibrium of certain annelated azoloazines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The first and second protonations of annelated azoloazines have been investigated quantitatively in aqueous solution. Compounds investigated were pyrazolo[1,5-a]pyrimidine (pKBH − 0.03±0.02, pKBH 2+ −7.87±0.30), 1,2,4-triazolo[4,3-b]-1,2,4-triazine (pKBH + −0.04±0.02, pKBH 2+ −8.00±0.10), 1,2,4-triazolo[1,5-a]pyrimidine (pKBH + 0.21±0.03, pKBH 2+ −9.00±0.09) and its 6R derivatives (R=NO2, Br, Cl). The annelated azoloazines studied are weaker bases than their unannelated analogs. According to quantum chemical calculations (AM1), protonation of these heterocycles may occur both at the azole and the azine fragments of the molecule.

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Authors and Affiliations

  1. St. Petersburg State Technological Institute, 198013, St Petersburg, Russia

    A. P. Volovodenko, R. E. Trifonov & V. A. Ostrovskii

  2. Institute of Organic Synthesis, Urals Branch, Russian Academy of Sciences (RAN), 620219, Ekaterinburg, Russia

    P. V. Plekhanov, G. L. Rusinov & D. G. Bresnev

Authors
  1. A. P. Volovodenko
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  2. R. E. Trifonov
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  3. P. V. Plekhanov
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  4. G. L. Rusinov
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  5. D. G. Bresnev
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  6. V. A. Ostrovskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 816–824, June, 2000.

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Volovodenko, A.P., Trifonov, R.E., Plekhanov, P.V. et al. Protolytic equilibrium of certain annelated azoloazines. Chem Heterocycl Compd 36, 714–721 (2000). https://doi.org/10.1007/BF02297681

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  • DOI: https://doi.org/10.1007/BF02297681

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