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

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

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2017, Volume: 66, Number: 11, Pages: 2095-2102 Pages count : DOI: 10.1007/s11172-017-1986-2

Tags

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

Authors

Pleshkova N. V. ¹ , Nikolaenkova E. B. ¹ , Krivopalov V. P. ¹ , Mamatyuk V. I. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Prosp Lavrentieva, Novosibirsk 630090, Russia
2	(Данные Web of science) Natl Res Univ, Novosibirsk State Univ, 2 Ul Pirogova, Novosibirsk 630090, Russia

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: Delta H = 15-28 kJ mol(-1); Delta S = 47-65 J mol(-1) De-1; D center dot (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.

Pleshkova N.V. , Nikolaenkova E.B. , Krivopalov V.P. , Mamatyuk V.I.
2,6-Disubstituted 4-azidopyrimidines: synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy
Russian Chemical Bulletin. 2017. V.66. N11. P.2095-2102. DOI: 10.1007/s11172-017-1986-2 WOS Scopus РИНЦ

Александрова Н.В. , Николаенкова Е.Б. , Кривопалов В.П. , Маматюк В.И.
2,6-дизамещенные 4-азидопиримидины: синтез и исследование кинетики и термодинамики азидо-тетразольной перегруппировки методами спектроскопии ямр
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2017. №11. С.2095-2102. РИНЦ

Published print:	Nov 1, 2017
Published online:	Mar 14, 2018

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