Isolation and Characterization of a Neutral Imino-semiquinone Radical
By Carter, Shawn M.; Sia, Allyson; Shaw, Michael J. & Heyduk, Alan F.
Published in Journal of the American Chemical Society
2008
Abstract
The neutral imino-semiquinone, 4,6-di-tert-butyl-2-tert-butylimino-semiquinone (isqH•), can be prepared by a conproportionation of the parent aminophenol and iminoquinone compounds. The neutral radical species has been characterized in the solid state by X-ray diffraction and in solution by EPR and UV-vis absorption spectroscopy. The stability of the open-shell radical is derived from the basicity of the tert-butylimino group and the intramolecular hydrogen bond.