First evidence for p-p dimerization of stable 1,4-dialkylquinoxalinium radical cations. Structure, spectroscopy, and magnetism

, , , , und . Zeitschrift fuer Naturforschung, B: A Journal of Chemical Sciences 48 (9): 1181--1186 (1993)


Crystal and mol. structure anal. of 1,4-diethylquinoxalinium iodide (I) shows a virtually planar quinoxaline ring with 11 conjugated p-electrons. In contrast to the triiodide of the 1,4,6,7-tetra-Me deriv. and to the tetraphenylborate salt of 1,4-diethylquinoxalinium cation radical, I exhibits p-p-dimerized radical cations in the solid state with synplanar Et groups and a rather small intermol. distance of about 315 pm between the p planes of the primarily interacting 1,4-diazine rings. Solid state magnetic measurements between 2 and 300 K show considerably diminished magnetic moments due to partial spin-pairing, and UV/VIS spectroscopic measurements in acetonitrile reflect the p-p interaction in soln. through the appearance of a long-wavelength absorption band. on SciFinder(R)

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