Isolation and characterization of a neutral imino-semiquinone radical.
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.
Carter
Shawn M
SM
Department of Chemistry, University of California, Irvine, California, 92697, USA.
Sia
Allyson
A
Shaw
Michael J
MJ
Heyduk
Alan F
AF
D016227:Benzoquinones / Q000737:chemistry* / Q000302:isolation & purification; D004563:Electrochemistry; D004578:Electron Spin Resonance Spectroscopy; D006863:Hydrogen-Ion Concentration; D007097:Imines / Q000737:chemistry* / Q000302:isolation & purification; D013816:Thermodynamics; D014961:X-Ray Diffraction
D016227:Benzoquinones; D007097:Imines; C025232:semiquinone radicals