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Research has been conducted on 2,4,6-tricyano-1,3,5-triazine. The authors report that the chemical reduction of this compound results in formation of unstable radical anion which dimerizes at a ring carbon.

Chemical reduction of 2,4,6-tricyano-1,3,5-triazine, TCT, results in the formation of an unstable radical anion that undergoes immediate dimerization at a ring carbon to form [C[sub 12]N[sub 12]][sup 2-] , [TCT][sub 2, sup 2-] , characterized by a long 1.570 (4) Å central C-C bond. [TCT][sub 2, sup 2-] can decompose into the radical anion of 4,4&;prime;,6,6'-tetracyano-2,2'-bitriazine, [TCBT][sup •-], the one-electron reduced form of planar (D[sub 2h]) TCBT, which is also structurally characterized as the [TMPD][TCBT] charge-transfer complex (TMPD = N,N,N'N'-tetramethyl-p-phenylenediamine) with a 1.492 (2) Å central sp²-sp² C-C bond. Although crystals could not be obtained for the radical anion [TCBT][sup •-], the electrochemistry (E° = +0.03 V), EPR (g = 2.003, ²A[sub [sup 14]N] = 3.347 G, and [sup 4]A[sub [sup 14]N] = 0.765 G and a line width of 0.24 G), and theoretical calculations support the formation of [TCBT][sup •-]. In addition, thermolysis of [TCT][sub 2, sup 2-] yields [TCBT][sup •-]. Chemical reduction of 2,4,6-tricyanobenzene, TCB, forms an unstable radical anion that immediately undoergoes dimerization at a ring carbon to form [C[sub 12]H[sub 6]N[sub 6]][sup 2-], [TCB][sub 2, sup 2-], which has a long 1.560 (5) Å central C-C bond. Reaction of TCT with tetrathiafulvalene (TTF) forms structurally characterized [TTF] [TCT], and in the presence of water, TCT hydrolyzes to 2,4-dicyano6-hydroxy-s-triazine, DCTOH. In contrast, the reaction of TCT with TMPD forms [TMPD] [TCT], which in the presence of water forms structurally characterized [HTMPD][sup +][DCTO][sup -]. [ABSTRACT FROM AUTHOR]