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Condensation of oxamidrazone with sulfur dichloride in acetonitrile affords 4,4‘-bis(1,2,3,5-dithiadiazolium) dichloride in moderate yield. Reduction of this salt with triphenylantimony yields the diradical 4,4‘-bis(1,2,3,5-dithiadiazolyl) [S2N2C−CN2S2], which has been isolated and characterized in the solid state as its dimer [S2N2C−CN2S2]2. The diradical is disjoint, and ab initio molecular orbital methods confirm a very small energy gap (<0.5 kcal/mol) between the triplet and diradical singlet states, regardless of the torsion angle about the central C−C bond. In accord with these theoretical predictions the ESR spectrum of the diradical consists (in CHCl3 at 273 K) of a simple five-line pattern (aN = 0.50 mT, g = 2.011), i.e., there is no observable exchange coupling between the two centers. In the solid state, the dimer [S2N2C−CN2S2]2 forms a slipped stack structure, with a mean intradimer S−S distance of 3.078 A and mean interdimer S- - -S contact of 3.761 A. Cosublimation of the diradical with iodi...

journal of the american chemical society

Preparation and Characterization of the Disjoint Diradical 4,4‘-Bis(1,2,3,5-dithiadiazolyl) [S2N2C−CN2S2] and Its Iodine Charge Transfer Salt [S2N2C−CN2S2][I]