Scientific article
Open access

A Potent Auto‐Umpolung Ligand for Conjugative Radical Stabilization

Published inChemistry, vol. 29, no. 3, e202203149
Publication date2022-11-22
First online date2022-11-22

Carbenes with conjugatively connected redox system act as “auto‐umpolung” ligands. Due to their electronic flexibility, they should also be particularly suitable to stabilize open‐shell species. Herein, the first neutral radical of such sort is described in form of a dialkylamino‐substituted bis(dicyanomethylene)cyclopropanide. Despite the absence of steric shielding, the radical is stable for an extended amount of time and was consequently characterized in solution via EPR measurements. These data and accompanying X‐ray structural analyses indicate that the radical species is in equilibrium with aggregates (formed via π‐stacking) and dimers (obtained via σ‐bond formation between methylene carbons).

  • EPR measurements
  • Carbene ligands
  • Cyclopropenium salts
  • Density functional calculations
  • Radicals
  • Deutsche Forschungsgemeinschaft - [EXC 2033 - 390677874]
  • Fonds der Chemischen Industrie -
Citation (ISO format)
HOLTHOFF, Jana M. et al. A Potent Auto‐Umpolung Ligand for Conjugative Radical Stabilization. In: Chemistry, 2022, vol. 29, n° 3, p. e202203149. doi: 10.1002/chem.202203149
Main files (1)
Article (Published version)
ISSN of the journal0947-6539

Technical informations

Creation12/28/2023 11:03:52 AM
First validation01/03/2024 3:37:56 PM
Update time01/03/2024 3:37:56 PM
Status update01/03/2024 3:37:56 PM
Last indexation05/06/2024 5:41:09 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack