2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and Properties

2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and Properties Full article

Journal

Molecules
, E-ISSN: 1420-3049

Output data

Year: 2020, Volume: 25, Number: 4, Article number : 845, Pages count : DOI: 10.3390/molecules25040845

Tags

nitroxides; nitrones; 1,3-dipolar cycloaddition reaction; organolithium compounds; EPR; spin probes; reduction kinetics

Authors

Zhurko Irina E. ¹ , Dobrynin Sergey ¹ , Gorodetskii Artem A. ¹ , Glazachev Yuri, I ² , Rybalova Tatyana, V ¹ , Chernyak Elena, I ¹ , Asanbaeva Nargiz ^1,3 , Bagryanskaya Elena G. ¹ , Kirilyuk Igor A. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Novosibirsk Inst Organ Chem, Siberian Branch, Academician Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Inst Chem Kinet & Combust SB RAS, Inst Skaya 3, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova St, Novosibirsk 2, Russia

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.

Zhurko I.E. , Dobrynin S. , Gorodetskii A.A. , Glazachev Y.I. , Rybalova T.V. , Chernyak E.I. , Asanbaeva N. , Bagryanskaya E.G. , Kirilyuk I.A.
2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and Properties

Molecules. 2020. V.25. N4. 845 . DOI: 10.3390/molecules25040845 WOS Scopus РИНЦ

Full text from publisher

Published online:

Feb 14, 2020

Web of science	WOS:000522454500081
Scopus	2-s2.0-85079610677
Elibrary	43241936
OpenAlex	W3006016581