2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls

Standard

2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls : Synthesis and properties. / Zhurko, Irina F.; Dobrynin, Sergey; Gorodetskii, Artem A. et al.

In: Molecules, Vol. 25, No. 4, 845, 14.02.2020.

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

Harvard

Zhurko, IF, Dobrynin, S, Gorodetskii, AA, Glazachev, YI, Rybalova, TV, Chernyak, EI, Asanbaeva, N, Bagryanskaya, EG & Kirilyuk, IA 2020, '2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls: Synthesis and properties', Molecules, vol. 25, no. 4, 845. https://doi.org/10.3390/molecules25040845

APA

Zhurko, I. F., Dobrynin, S., Gorodetskii, A. A., Glazachev, Y. I., Rybalova, T. V., Chernyak, E. I., Asanbaeva, N., Bagryanskaya, E. G., & Kirilyuk, I. A. (2020). 2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls: Synthesis and properties. Molecules, 25(4), [845]. https://doi.org/10.3390/molecules25040845

Vancouver

Zhurko IF, Dobrynin S, Gorodetskii AA, Glazachev YI, Rybalova TV, Chernyak EI et al. 2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls: Synthesis and properties. Molecules. 2020 Feb 14;25(4):845. doi: 10.3390/molecules25040845

Author

Zhurko, Irina F. ; Dobrynin, Sergey ; Gorodetskii, Artem A. et al. / 2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls : Synthesis and properties. In: Molecules. 2020 ; Vol. 25, No. 4.

BibTeX

@article{8d2c8982796d4e10abe6721b7e43c64b,

title = "2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls: Synthesis and properties",

abstract = "Nitroxides are broadly used as molecular probes and labels in biophysics, structural biology, and biomedical research. Resistance of a nitroxide group bearing an unpaired electron to chemical reduction with low-molecular-weight antioxidants and enzymatic systems is of critical importance for these applications. The redox properties of nitroxides are known to depend on the ring size (for cyclic nitroxides) and electronic and steric effects of the substituents. Here, two highly strained nitroxides, 5-(tert-butyl)-5-butyl-2,2-diethyl-3-hydroxypyrrolidin-1-oxyl (4) and 2-(tert-butyl)-2-butyl-5,5-diethyl-3,4-bis(hydroxymethyl)pyrrolidin-1-oxyl (5), were prepared via a reaction of the corresponding 2-tert-butyl-1-pyrroline 1-oxides with butyllithium. Thermal stability and kinetics of reduction of the new nitroxides by ascorbic acid were studied. Nitroxide 5 showed the highest resistance to reduction.",

keywords = "1,3-dipolar cycloaddition reaction, EPR, Nitrones, Nitroxides, Organolithium compounds, Reduction kinetics, Spin probes, NITROXIDE, reduction kinetics, nitroxides, 2-SUBSTITUTED 5,5-DIMETHYL-4-OXO-1-PYRROLINE-1-OXIDES, PYRROLINE, organolithium compounds, spin probes, ALKOXYAMINES, REDUCTION, nitrones, RADICALS, PHOTOLYSIS, DERIVATIVES, EPR SPECTROSCOPY, IMIDAZOLIDINE",

author = "Zhurko, {Irina F.} and Sergey Dobrynin and Gorodetskii, {Artem A.} and Glazachev, {Yuri I.} and Rybalova, {Tatyana V.} and Chernyak, {Elena I.} and Nargiz Asanbaeva and Bagryanskaya, {Elena G.} and Kirilyuk, {Igor A.}",

year = "2020",

month = feb,

day = "14",

doi = "10.3390/molecules25040845",

language = "English",

volume = "25",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "4",

}

RIS

TY - JOUR

T1 - 2‐Butyl‐2‐tert‐butyl‐5,5‐diethylpyrrolidine‐1‐oxyls

T2 - Synthesis and properties

AU - Zhurko, Irina F.

AU - Dobrynin, Sergey

AU - Gorodetskii, Artem A.

AU - Glazachev, Yuri I.

AU - Rybalova, Tatyana V.

AU - Chernyak, Elena I.

AU - Asanbaeva, Nargiz

AU - Bagryanskaya, Elena G.

AU - Kirilyuk, Igor A.

PY - 2020/2/14

Y1 - 2020/2/14

N2 - Nitroxides are broadly used as molecular probes and labels in biophysics, structural biology, and biomedical research. Resistance of a nitroxide group bearing an unpaired electron to chemical reduction with low-molecular-weight antioxidants and enzymatic systems is of critical importance for these applications. The redox properties of nitroxides are known to depend on the ring size (for cyclic nitroxides) and electronic and steric effects of the substituents. Here, two highly strained nitroxides, 5-(tert-butyl)-5-butyl-2,2-diethyl-3-hydroxypyrrolidin-1-oxyl (4) and 2-(tert-butyl)-2-butyl-5,5-diethyl-3,4-bis(hydroxymethyl)pyrrolidin-1-oxyl (5), were prepared via a reaction of the corresponding 2-tert-butyl-1-pyrroline 1-oxides with butyllithium. Thermal stability and kinetics of reduction of the new nitroxides by ascorbic acid were studied. Nitroxide 5 showed the highest resistance to reduction.

AB - Nitroxides are broadly used as molecular probes and labels in biophysics, structural biology, and biomedical research. Resistance of a nitroxide group bearing an unpaired electron to chemical reduction with low-molecular-weight antioxidants and enzymatic systems is of critical importance for these applications. The redox properties of nitroxides are known to depend on the ring size (for cyclic nitroxides) and electronic and steric effects of the substituents. Here, two highly strained nitroxides, 5-(tert-butyl)-5-butyl-2,2-diethyl-3-hydroxypyrrolidin-1-oxyl (4) and 2-(tert-butyl)-2-butyl-5,5-diethyl-3,4-bis(hydroxymethyl)pyrrolidin-1-oxyl (5), were prepared via a reaction of the corresponding 2-tert-butyl-1-pyrroline 1-oxides with butyllithium. Thermal stability and kinetics of reduction of the new nitroxides by ascorbic acid were studied. Nitroxide 5 showed the highest resistance to reduction.

KW - 1,3-dipolar cycloaddition reaction

KW - EPR

KW - Nitrones

KW - Nitroxides

KW - Organolithium compounds

KW - Reduction kinetics

KW - Spin probes

KW - NITROXIDE

KW - reduction kinetics

KW - nitroxides

KW - 2-SUBSTITUTED 5,5-DIMETHYL-4-OXO-1-PYRROLINE-1-OXIDES

KW - PYRROLINE

KW - organolithium compounds

KW - spin probes

KW - ALKOXYAMINES

KW - REDUCTION

KW - nitrones

KW - RADICALS

KW - PHOTOLYSIS

KW - DERIVATIVES

KW - EPR SPECTROSCOPY

KW - IMIDAZOLIDINE

UR - http://www.scopus.com/inward/record.url?scp=85079610677&partnerID=8YFLogxK

U2 - 10.3390/molecules25040845

DO - 10.3390/molecules25040845

M3 - Article

C2 - 32075085

AN - SCOPUS:85079610677

VL - 25

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 4

M1 - 845

ER -

ID: 23594367