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Crystal structures of alkali salts of tetrahalogenosemiquinone anion radical acetone solvates and their solvent-free salts are determined. p-Semiquinone anion radical reveals enhanced aromaticity of the ring compared to the quinone. A pair of pi-stacked radical anion (p-semiquinone) rings occurs in crystal structures of potassium and rubidium salts of tetrachlorosemiquinone anion acetone solvates and their potassium tetrabromo analogue. The ring centroid separation distances are about 3.2 A and carbon-carbon contacts between the contiguous rings are 0.3 A shorter than the sum of van der Waals radii. The spin-coupling of the two unpaired electrons between the two anion radical rings (forming a stacked dimer) correlates with the diamagnetic property of the crystals. Magnetic properties of alkali salts of tetrahalogenosemiquinone anion radical acetone solvates were examined by electron paramagnetic resonance spectroscopy

Stabilisation of tetrabromo- and tetrachlorosemiquinone (bromanil and chloranil) anion radicals in crystals