Redox-Amphoteric 4,4’-Dicyclopropyldiphenylnitroxyl Radical: Unexpectedly High Stability

Dmitry Dulov, Oleg Levitskiy, Alexey Bogdanov, Tatiana Magdesieva*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Atom-economy cyclopropyl group turned out to be the substituent of choice for stabilization of diphenylnitroxyl radical in solution (τ1/2=1280 h, i. e., ca. 2 months, in benzene). Though the benzylic H-atom commonly provokes fast decomposition of nitroxides in solution and the cyclopropyl moiety is prone to the ring opening in substrates with significant spin density at the α-position, both processes are not implemented in 4,4’-dicyclopropyldiphenylnitroxide. Instead, the stereoelectronic properties of the cyclopropyl group lead to significant stabilization of the oxidized and reduced states of the nitroxide, making it redox-amphoteric and suitable for practical application.

Original languageEnglish
Pages (from-to)9653-9656
Number of pages4
JournalChemistrySelect
Volume6
Issue number36
DOIs
Publication statusPublished - 27 Sept 2021
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry

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