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

Authors :
Viktor P. Krivopalov
Elena B. Nikolaenkova
V. I. Mamatyuk
N. V. Pleshkova
Source :
Russian Chemical Bulletin. 66:2095-2102
Publication Year :
2017
Publisher :
Springer Science and Business Media LLC, 2017.

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; 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.

Details

ISSN :
15739171 and 10665285
Volume :
66
Database :
OpenAIRE
Journal :
Russian Chemical Bulletin
Accession number :
edsair.doi...........25833b4fa3e6396e0ac1ddb87d7ea413
Full Text :
https://doi.org/10.1007/s11172-017-1986-2