2-(8H-Benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol-4-ylidene)-malononitrile | 139313-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(8H-Benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol-4-ylidene)-malononitrile
• CAS: 139313-70-5
• 化学式: C₉H₂N₆S₂
• 分子量: 258.287
• InChiKey: VFBOQBYBXKPXCT-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  2-(8H-Benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol-4-ylidene)-malononitrile 在 selenium(IV) oxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以50%的产率得到2-(8'-Dicyanomethylene-8'H-[4,4']bi[benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazolylidene]-8-ylidene)-malononitrile
  参考文献：
  名称：

  Isolation and X-ray Structural Determination of Both Folded and Twisted Conformers of Bis{4H,8H-4-(dicyanomethylene)-benzo[1,2-c:4,5-c′]bis[1,2,5]thiadiazol-8-ylidene}, an Overcrowded Ethylene with High Electron Affinity

  摘要：

  DOI：

  10.1002/anie.199724951
• 作为产物：
  描述：

  4,8-bis(dicyanomethyl)benzo<1,2-c:4,5-c'>bis<1,2,5>thiadiazole 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以73%的产率得到2-(8H-Benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazol-4-ylidene)-malononitrile
  参考文献：
  名称：

  Clathrate formation and molecular recognition by novel chalcogen-cyano interactions in tetracyanoquinodimethanes fused with thiadiazole and selenadiazole rings

  摘要：

  The intermolecular contacts between chalcogen atoms and cyano lone pairs were found to stabilize the crystalline state by electrostatic interaction. This interaction is one of the sources of the directionality in crystal packing of organic molecules and causes the formation of various types of inclusion lattices in the charge-transfer (CT) crystals of 1-3. By using highly selective formation of CT crystals with substituted aromatic hydrocarbons, particular isomers such as p-xylene or 2,6-dimethylnaphthalene (2,6-DMN) could be separated from the corresponding isomer mixtures. Lattice-related interaction plays a more significant role than molecular orbital interaction in the observed selectivity for para-disubstituted benzenes. However, the latter interaction is important for the recognition of 2,6-DMN from the 2,7 isomer.

  DOI：

  10.1021/ja00034a041