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

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: Δ H = 15—28 kJ mol –1 ; Δ S = 47—65 J mol –1 К–1; Е a = 93—117 kJ mol –1 ; lg A = 15.1—18.9. They are dependent on electron...

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Bibliographic Details
Published in:Russian chemical bulletin 2017-11, Vol.66 (11), p.2095-2102
Main Authors: Pleshkova, N. V., Nikolaenkova, E. B., Krivopalov, V. P., Mamatyuk, V. I.
Format: Article
Language:English
Subjects:
ARRHENIUS EQUATION
AZIDES
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
ENTHALPY
ENTROPY
EQUILIBRIUM
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Inorganic Chemistry
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
NMR
NMR spectroscopy
NUCLEAR MAGNETIC RESONANCE
Organic Chemistry
Polarity
PYRIMIDINES
SOLVENTS
SPECTROSCOPY
SYNTHESIS
TETRAZOLES
THERMODYNAMICS
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Summary: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: Δ H = 15—28 kJ mol –1 ; Δ S = 47—65 J mol –1 К–1; Е a = 93—117 kJ mol –1 ; lg A = 15.1—18.9. They are dependent on electronic properties of the substituents and the polarity of solvent.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-017-1986-2