Twisted Diarylnitroxides: An Efficient Route for Radical Stabilization

Oleg A. Levitskiy, Dmitry B. Eremin, Alexey V. Bogdanov, Tatiana V. Magdesieva*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

New strategy for the molecular design of stable diarylnitroxides was elaborated based on the insertion of a bulky substituent into the ortho-position of the phenyl ring thus disturbing its conjugation with the radical center. A series of new twisted diaryl nitroxides with tert-butyl and trifluoromethyl substituents in different positions and combinations was obtained and fully characterized. Electron spin resonance (ESR) and density functional theory (DFT) studies confirmed that the ortho-substituted phenyl ring is removed from the conjugation; the O–N–C–C torsion angle was shown to be dependent not only on the bulkiness of the ortho-substituent, but it is also influenced by the electron-donating or electron-withdrawing ability of the substituents in both phenyl rings. These nitroxides constitute the first examples of stable diarylnitroxides with a vacant para-position on the phenyl ring. The new approach will broaden the scope of available stable diarylnitroxyl radicals, which are practically important.

Original languageEnglish
Pages (from-to)4726-4735
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number32
DOIs
Publication statusPublished - 1 Sept 2017
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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