o-Quinonoid heterocycles: synthesis and crystal structure of 2,3-dicyano-5,7-bismethylthieno[3,4-b]pyrazine |
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Authors: | Mørkved Eva H Beukes Jon A Mo Frode |
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Institution: | Department of Chemistry, Norwegian University of Science and Technology, N-7491 Trondheim, Norway. eva.morkved@chem.ntnu.no |
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Abstract: | 2,3-Dicyano-5,7-bismethylthieno3,4-b]pyrazine (5), has been obtained as a minor product from reactions of S-nucleophiles with 5,6-di(1-bromoethyl)pyrazine-2,3-dicarbonitrile (3), or from a condensation of 4-hydroxy-2,5-dimethyl-2,3-dihydrothiophen-3-one (4) with diaminomaleonitrile. The molecular structure of compound 5 has been confirmed by X-ray diffraction. A partial separation of charge causes a donor-acceptor type arrangement of the planar molecules in uniform parallel stacks with an interplanar spacing of 3.334(2) A at 100 K. |
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