Russian Chemical Bulletin

, Volume 66, Issue 11, pp 2095–2102 | Cite as

2,6-Disubstituted 4-azidopyrimidines: synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy

  • N. V. Pleshkova
  • E. B. Nikolaenkova
  • V. P. Krivopalov
  • V. I. Mamatyuk
Full Article


Thermodynamic and kinetic parameters of the tautomeric tetrazole-azide rearrangement for a series of 2,6-disubstituted 4-azidopyrimidines are determined by NOESY/EXSY and DNMR: ΔH = 15—28 kJ mol–1; ΔS = 47—65 J mol–1 К–1; Е a = 93—117 kJ mol–1; lgA = 15.1—18.9. They are dependent on electronic properties of the substituents and the polarity of solvent.

Key words

4-azidopyrimidine tetrazolo[c]pyrimidines azide-tetrazole equilibrium NMR NOESY/EXSY DNMR entropy enthalpy rate constant Arrhenius equation 


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© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  • N. V. Pleshkova
    • 1
  • E. B. Nikolaenkova
    • 1
  • V. P. Krivopalov
    • 1
  • V. I. Mamatyuk
    • 1
    • 2
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian BranchRussian Academy of SciencesNovosibirskRussian Federation
  2. 2.Novosibirsk State University (National Research University)NovosibirskRussian Federation

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