Carbon- and SO2-Locked Diarylnitroxides: Quantum Chemical Consideration, Synthesis, and Electrochemistry

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Selection of linkers connecting two phenyl rings as a part of molecular design of diarylnitroxides with increased kinetic stability of redox forms was performed using quantum chemical estimation of the geometry and oxidation potential values. It revealed that introduction of the carbon bridge cannot be considered as efficient “instrument” for structural tuning of the nitroxide properties since altering neither the length of the bridge nor its position results in significant changes in the oxidation potential, in contrast to a heteroatomic bridge, which makes more perturbation in the electronic structure of diarylnitroxide. To support the prediction, new SO2-bridged diarylnitroxide was synthesized and characterized using spectral and electrochemical methods. It is extremely stable in benzene solution, exhibits the maximal anodic potential value achieved for reversibly oxidized nitroxides to date (1.33 V, Ag/AgCl/KCl) and seems promising as cathodic redox active material providing maximal potential gap as compared to the previously reported compounds.

Original languageEnglish
Pages (from-to)6225-6231
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number36
DOIs
Publication statusPublished - 30 Sept 2019
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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