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 language | English |
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Pages (from-to) | 9653-9656 |
Number of pages | 4 |
Journal | ChemistrySelect |
Volume | 6 |
Issue number | 36 |
DOIs | |
Publication status | Published - 27 Sept 2021 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- General Chemistry