Email this article 2,6-Disubstituted 4-azidopyrimidines: synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy
- Authors: Pleshkova N.V.1, Nikolaenkova E.B.1, Krivopalov V.P.1, Mamatyuk V.I.1,2
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Affiliations:
- N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch, Russian Academy of Sciences
- Novosibirsk State University (National Research University)
- Issue: Vol 66, No 11 (2017)
- Pages: 2095-2102
- Section: Full Article
- URL: https://journals.rcsi.science/1066-5285/article/view/241562
- DOI: https://doi.org/10.1007/s11172-017-1986-2
- ID: 241562
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Abstract
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; Еa = 93—117 kJ mol–1; lgA = 15.1—18.9. They are dependent on electronic properties of the substituents and the polarity of solvent.
About the authors
N. V. Pleshkova
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch, Russian Academy of Sciences
Author for correspondence.
Email: Nadia789@nioch.nsc.ru
Russian Federation, 9 prosp. Lavrentieva, Novosibirsk, 630090
E. B. Nikolaenkova
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch, Russian Academy of Sciences
Email: Nadia789@nioch.nsc.ru
Russian Federation, 9 prosp. Lavrentieva, Novosibirsk, 630090
V. P. Krivopalov
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch, Russian Academy of Sciences
Email: Nadia789@nioch.nsc.ru
Russian Federation, 9 prosp. Lavrentieva, Novosibirsk, 630090
V. I. Mamatyuk
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch, Russian Academy of Sciences; Novosibirsk State University (National Research University)
Email: Nadia789@nioch.nsc.ru
Russian Federation, 9 prosp. Lavrentieva, Novosibirsk, 630090; 2 ul. Pirogova, Novosibirsk, 630090
