4,5,6,7-tetrachloro-2-dicyanomethyleneindane-1,3-dione | 147973-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4,5,6,7-tetrachloro-2-dicyanomethyleneindane-1,3-dione
• 英文别名: 2-(4,5,6,7-Tetrachloro-1,3-dioxoinden-2-ylidene)propanedinitrile
• CAS: 147973-52-2
• 化学式: C₁₂Cl₄N₂O₂
• 分子量: 345.956
• InChiKey: UARRBSVJBXXJTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四硫富瓦烯 、 4,5,6,7-tetrachloro-2-dicyanomethyleneindane-1,3-dione 以 乙腈 为溶剂， 以21%的产率得到
  参考文献：
  名称：

  Studies on π-acceptor molecules containing the dicyanomethylene group. X-Ray crystal structure of the charge-transfer complex of tetramethyltetrathiafulvalene and 2,3-dicyano-1,4-naphthoquinone: (TMTTF)₃–(DCNQ)₂

  摘要：

  The reaction of tetramethyltetrathiafulvalene (TMTTF, 7) with 2-dicyanomethyleneindane-1,3-dione (DCID, 1) leads to isomerisation of DCID to 2,3-dicyanonaphthoquinone (DCNQ, 3) to yield the charge-transfer complex [(TMTTF)3]2.+-(DCNQ.-)2 8. The X-ray crystal structure of complex 8 reveals stacks of TMTTF molecules along the x direction in the sequence A..B..A..A..B..A.. etc. The A..A and A..B interplanar separation distances are 3.51 angstrom and 3.44 angstrom, respectively. The DCNQ radical anions form dimers, with a remarkably short interplanar separation of 3.02 angstrom, which are orthogonal to the TMTTF stacks. The complex is diamagnetic. Other pi-acceptor molecules containing the dicyanomethylene group, viz. compounds 2 and 10-12, have been prepared and their redox properties studied by cyclic voltammetry. Compound 2 rearranges to compound 4 on complexation with TTF 6. DCID derivatives 1 and 2 react with a range of amines, by displacement of one cyano group, to yield enamines 15-19; the amphiphilic compound 18 forms Langmuir-Blodgett films which exhibit weak second harmonic generation.

  DOI：

  10.1039/p29930000313
• 作为产物：
  描述：

  4,5,6,7-四氯茚满-1,3-二酮 、 四氰基乙烯 以 乙醇 为溶剂， 反应 0.5h， 以79%的产率得到4,5,6,7-tetrachloro-2-dicyanomethyleneindane-1,3-dione
  参考文献：
  名称：

  Studies on π-acceptor molecules containing the dicyanomethylene group. X-Ray crystal structure of the charge-transfer complex of tetramethyltetrathiafulvalene and 2,3-dicyano-1,4-naphthoquinone: (TMTTF)₃–(DCNQ)₂

  摘要：

  The reaction of tetramethyltetrathiafulvalene (TMTTF, 7) with 2-dicyanomethyleneindane-1,3-dione (DCID, 1) leads to isomerisation of DCID to 2,3-dicyanonaphthoquinone (DCNQ, 3) to yield the charge-transfer complex [(TMTTF)3]2.+-(DCNQ.-)2 8. The X-ray crystal structure of complex 8 reveals stacks of TMTTF molecules along the x direction in the sequence A..B..A..A..B..A.. etc. The A..A and A..B interplanar separation distances are 3.51 angstrom and 3.44 angstrom, respectively. The DCNQ radical anions form dimers, with a remarkably short interplanar separation of 3.02 angstrom, which are orthogonal to the TMTTF stacks. The complex is diamagnetic. Other pi-acceptor molecules containing the dicyanomethylene group, viz. compounds 2 and 10-12, have been prepared and their redox properties studied by cyclic voltammetry. Compound 2 rearranges to compound 4 on complexation with TTF 6. DCID derivatives 1 and 2 react with a range of amines, by displacement of one cyano group, to yield enamines 15-19; the amphiphilic compound 18 forms Langmuir-Blodgett films which exhibit weak second harmonic generation.

  DOI：

  10.1039/p29930000313

文献信息

• Studies on π-acceptor molecules containing the dicyanomethylene group. X-Ray crystal structure of the charge-transfer complex of tetramethyltetrathiafulvalene and 2,3-dicyano-1,4-naphthoquinone: (TMTTF)₃–(DCNQ)₂
  作者：Andrei S. Batsanov、Martin R. Bryce、Stephen R. Davies、Judith A. K. Howard、Roger Whitehead、Brian K. Tanner

  DOI：10.1039/p29930000313

  日期：——

  The reaction of tetramethyltetrathiafulvalene (TMTTF, 7) with 2-dicyanomethyleneindane-1,3-dione (DCID, 1) leads to isomerisation of DCID to 2,3-dicyanonaphthoquinone (DCNQ, 3) to yield the charge-transfer complex [(TMTTF)3]2.+-(DCNQ.-)2 8. The X-ray crystal structure of complex 8 reveals stacks of TMTTF molecules along the x direction in the sequence A..B..A..A..B..A.. etc. The A..A and A..B interplanar separation distances are 3.51 angstrom and 3.44 angstrom, respectively. The DCNQ radical anions form dimers, with a remarkably short interplanar separation of 3.02 angstrom, which are orthogonal to the TMTTF stacks. The complex is diamagnetic. Other pi-acceptor molecules containing the dicyanomethylene group, viz. compounds 2 and 10-12, have been prepared and their redox properties studied by cyclic voltammetry. Compound 2 rearranges to compound 4 on complexation with TTF 6. DCID derivatives 1 and 2 react with a range of amines, by displacement of one cyano group, to yield enamines 15-19; the amphiphilic compound 18 forms Langmuir-Blodgett films which exhibit weak second harmonic generation.