Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 24, Pages 8049-8052Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902265
Keywords
cyclopropenium; ligand dissociation; O-centered radicals; oxidation; radical cations
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Funding
- NIGMS [R01 GM102611, R35 GM127135]
- National Science Foundation [DGE-16-44869]
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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.
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