Oxidizable Ketones: Persistent Radical Cations from the Single‐Electron Oxidation of 2,3‐Diaminocyclopropenones. | Zendy

Strater Zack M. | Zendy; Rauch Michael | Zendy; Jockusch Steffen | Zendy; Lambert Tristan H. | Zendy

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Oxidizable Ketones: Persistent Radical Cations from the Single‐Electron Oxidation of 2,3‐Diaminocyclopropenones.

Author(s) -

Strater Zack M.,

Rauch Michael,

Jockusch Steffen,

Lambert Tristan H.

Publication year - 2019

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201902265

Subject(s) - electron paramagnetic resonance , heteroatom , chemistry , radical ion , cyclic voltammetry , ion , metal , photochemistry , ligand (biochemistry) , electron , oxygen , electrochemistry , crystallography , medicinal chemistry , inorganic chemistry , ring (chemistry) , organic chemistry , electrode , nuclear magnetic resonance , biochemistry , physics , receptor , quantum mechanics

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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