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

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

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Article number845
Number of pages17
JournalMolecules
Volume25
Issue number4
DOIs
Publication statusPublished - 14 Feb 2020

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

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