N,7,7-tricyanoquinone methide imine | 116267-99-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,7,7-tricyanoquinone methide imine
• 英文别名: N,7,7-tricyanoquinomethanimine；4-(Dicyanomethylene)-2,5-cyclohexadien-1-ylidenecyanamide；[4-(dicyanomethylidene)cyclohexa-2,5-dien-1-ylidene]cyanamide
• CAS: 116267-99-3
• 化学式: C₁₀H₄N₄
• 分子量: 180.169
• InChiKey: PPPJNKXQPGCECC-UHFFFAOYSA-N

物化性质

• 沸点：
  279.9±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,7,7-tricyanoquinone methide imine 在 氢化钾 作用下， 以 乙二醇二甲醚 为溶剂， 生成
  参考文献：
  名称：

  New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives

  摘要：

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.

  DOI：

  10.1021/jo00032a017
• 作为产物：
  描述：

  二(三甲基硅基)碳酰二亚胺 、 7,7-dicyanobenzoquinone methide 在 四氯化钛 作用下， 以 苯 为溶剂， 反应 72.0h， 以47%的产率得到N,7,7-tricyanoquinone methide imine
  参考文献：
  名称：

  新型受电子醌甲基亚胺的制备及其聚合

  摘要：

  N,7,7-三氰基醌甲基亚胺 (1)、N,11,11-三氰基-1,4-萘醌甲基亚胺 (2) 和 N,15,15-三氰基-9,10-蒽醌甲基亚胺 (3) ) 被成功制备为新型的受电子醌甲基亚胺化合物。1 可与自由基和阴离子引发剂均聚，而 2 和 3 则不能。

  DOI：

  10.1246/cl.1988.1187

文献信息

• Preparation of Novel Electron-Accepting Quinone Methide Imines and Their Polymerizations
  作者：Shouji Iwatsuki、Takahito Itoh、Hiromu Itoh

  DOI：10.1246/cl.1988.1187

  日期：1988.7.5

  N,7,7-Tricyanoquinone methide imine (1), N,11,11-tricyano-1,4-naphthoquinone methide imine (2), and N,15,15-tricyano-9,10-anthraquinone methide imine (3) were successfully prepared as novel electron-accepting quinone methide imine compounds. 1 is homopolymerizable with free radical and anionic initiators, while 2 and 3 are not.

  N,7,7-三氰基醌甲基亚胺 (1)、N,11,11-三氰基-1,4-萘醌甲基亚胺 (2) 和 N,15,15-三氰基-9,10-蒽醌甲基亚胺 (3) ) 被成功制备为新型的受电子醌甲基亚胺化合物。1 可与自由基和阴离子引发剂均聚，而 2 和 3 则不能。
• Stabilization of Magnetic Ordering Observed for the Bridging NCN Group
  作者：Jordan L. Arthur、Curtis E. Moore、Arnold L. Rheingold、Joel S. Miller

  DOI：10.1021/ic200083j

  日期：2011.4.4

  The reaction of meso-tetraphenylporphyrina: tomanganese(II) (MnTPP) and. N,7,7-tricyanoquinomethanimine (TCQMI) forms [(MnTPP)-T-III](+)}(2)[TCQMI](2)(2-), which possesses a one-dimensional chain with mu(1,3)-NCN linkages. The reduced [TCQMI](center dot-) dimerizes as [TCQMI](2)(2-) with a long, central 1.611(8) angstrom C-C bond and leads to a honeycomb, two-dimensionally layered structure with 24-membered rings. The mu(1,3)-NCN linkage stabilizes a canted antiferromagnetic (weak ferromagnetic) behavior with T-c of 3.7 K.
• New electron acceptors: synthesis, electrochemistry, and radical anions of N,7,7-tricyanoquinomethanimines and x-ray crystal structures of the trimethyl and tetramethyl derivatives
  作者：Martin R. Bryce、Stephen R. Davies、Andrew M. Grainger、Michael B. Hursthouse、Mohammed Mazid、Rainer Bachmann、Fabian Gerson、Jonas Hellberg

  DOI：10.1021/jo00032a017

  日期：1992.3

  The reaction of a range of quinones 3 with malononitrile in the presence of titanium tetrachloride/pyridine yields dicyanoquinomethides 4, which on reaction with N,N'-bis(trimethylsilyl)carbodiimide are converted into the corresponding N,7,7-tricyanoquinomethanimines 6. The solution electrochemical redox properties of compounds 6 have been studied by cyclic voltammetry; they are strong acceptors which readily form radical anions and dianions. The radical anions of N,7,7-tricyanoquinodimethanimine 6a and the tetra-, tri- and dimethyl derivatives 6c, 6d, and 6e, respectively, have been studied by ESR and ENDOR spectroscopy. X-ray crystal structure analysis reveals that trimethyl derivative 6d is planar, whereas the tetramethyl derivative 6c is strongly deformed with the ring existing in a boat conformation, similar to that found previously for tetrasubstituted TCNQ derivatives.