Single electron oxidation of 2,3‐diaminocyclopropenones is shown to give rise to stable diaminocyclopropenium oxyl (DACO) radical cations. Cyclic voltammetry reveals reversible oxidations in the range of +0.70–1.10 V (vs. SCE). Computational, EPR, and X‐ray analysis support the view that the oxidized species is best described as a cyclopropenium ion with spin density located on the heteroatom substituents, including 23.5 % on oxygen. The metal–ligand behavior of the DACO radical is also described.
Oxidizable Ketones: Persistent Radical Cations from the Single‐Electron Oxidation of 2,3‐Diaminocyclopropenones.
Single electron oxidation of 2,3‐diaminocyclopropenones is shown to give rise to stable diaminocyclopropenium oxyl (DACO) radical cations. Cyclic voltammetry reveals reversible oxidations in the range of +0.70–1.10 V (vs. SCE). Computational, EPR, and X‐ray analysis support the view that the oxidized species is best described as a cyclopropenium ion with spin density located on the heteroatom substituents, including 23.5 % on oxygen. The metal–ligand behavior of the DACO radical is also described.
more » « less- NSF-PAR ID:
- 10102901
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- Angewandte Chemie
- Volume:
- 131
- Issue:
- 24
- ISSN:
- 0044-8249
- Page Range / eLocation ID:
- p. 8133-8136
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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