2,6-Disubstituted 4-azidopyrimidines

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2,6-Disubstituted 4-azidopyrimidines : synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy. / Pleshkova, N. V.; Nikolaenkova, E. B.; Krivopalov, V. P. et al.

In: Russian Chemical Bulletin, Vol. 66, No. 11, 01.11.2017, p. 2095-2102.

Research output: Contribution to journal › Article › peer-review

Harvard

Pleshkova, NV, Nikolaenkova, EB, Krivopalov, VP & Mamatyuk, VI 2017, '2,6-Disubstituted 4-azidopyrimidines: synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy', Russian Chemical Bulletin, vol. 66, no. 11, pp. 2095-2102. https://doi.org/10.1007/s11172-017-1986-2

APA

Pleshkova, N. V., Nikolaenkova, E. B., Krivopalov, V. P., & Mamatyuk, V. I. (2017). 2,6-Disubstituted 4-azidopyrimidines: synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy. Russian Chemical Bulletin, 66(11), 2095-2102. https://doi.org/10.1007/s11172-017-1986-2

Vancouver

Pleshkova NV, Nikolaenkova EB, Krivopalov VP, Mamatyuk VI. 2,6-Disubstituted 4-azidopyrimidines: synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy. Russian Chemical Bulletin. 2017 Nov 1;66(11):2095-2102. doi: 10.1007/s11172-017-1986-2

Author

Pleshkova, N. V. ; Nikolaenkova, E. B. ; Krivopalov, V. P. et al. / 2,6-Disubstituted 4-azidopyrimidines : synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy. In: Russian Chemical Bulletin. 2017 ; Vol. 66, No. 11. pp. 2095-2102.

BibTeX

@article{af008f894d7147d791908e60bfa03a61,

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

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.",

keywords = "4-azidopyrimidine, Arrhenius equation, azide-tetrazole equilibrium, DNMR, enthalpy, entropy, NMR, NOESY/EXSY, rate constant, tetrazolo[c]pyrimidines, SERIES, 2-AZIDOPYRIMIDINES, ISOMERIZATION, H-1-N-15, COUPLING-CONSTANTS, AROMATICITY, HETEROCYCLES, SYSTEMS, TAUTOMERISM, AZIDE/TETRAZOLE EQUILIBRIUM",

author = "Pleshkova, {N. V.} and Nikolaenkova, {E. B.} and Krivopalov, {V. P.} and Mamatyuk, {V. I.}",

note = "Publisher Copyright: {\textcopyright} 2017, Springer Science+Business Media, LLC, part of Springer Nature.",

year = "2017",

month = nov,

day = "1",

doi = "10.1007/s11172-017-1986-2",

language = "English",

volume = "66",

pages = "2095--2102",

journal = "Russian Chemical Bulletin",

issn = "1066-5285",

publisher = "Springer Nature",

number = "11",

}

RIS

TY - JOUR

T1 - 2,6-Disubstituted 4-azidopyrimidines

T2 - synthesis, kinetic and thermodynamic studies of azide-tetrazole rearrangement by NMR spectroscopy

AU - Pleshkova, N. V.

AU - Nikolaenkova, E. B.

AU - Krivopalov, V. P.

AU - Mamatyuk, V. I.

PY - 2017/11/1

Y1 - 2017/11/1

N2 - 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.

AB - 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.

KW - 4-azidopyrimidine

KW - Arrhenius equation

KW - azide-tetrazole equilibrium

KW - DNMR

KW - enthalpy

KW - entropy

KW - NMR

KW - NOESY/EXSY

KW - rate constant

KW - tetrazolo[c]pyrimidines

KW - SERIES

KW - 2-AZIDOPYRIMIDINES

KW - ISOMERIZATION

KW - H-1-N-15

KW - COUPLING-CONSTANTS

KW - AROMATICITY

KW - HETEROCYCLES

KW - SYSTEMS

KW - TAUTOMERISM

KW - AZIDE/TETRAZOLE EQUILIBRIUM

UR - http://www.scopus.com/inward/record.url?scp=85043980194&partnerID=8YFLogxK

U2 - 10.1007/s11172-017-1986-2

DO - 10.1007/s11172-017-1986-2

M3 - Article

AN - SCOPUS:85043980194

VL - 66

SP - 2095

EP - 2102

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 11

ER -

ID: 12179254