4,5-ethylenedithio-4',5'-dicarbamoyltetrathiafulvalene | 609847-57-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 4,5-ethylenedithio-4',5'-dicarbamoyltetrathiafulvalene
• 英文别名: 2-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-1,3-dithiole-4,5-dicarboxamide；2-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-1,3-dithiole-4,5-dicarboxamide
• CAS: 609847-57-6
• 化学式: C₁₀H₈N₂O₂S₆
• 分子量: 380.582
• InChiKey: MLBVPUKNFZXZHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  238
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  四丁基高铼酸铵 、 4,5-ethylenedithio-4',5'-dicarbamoyltetrathiafulvalene 以 四氢呋喃 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Singular Crystalline β‘-Layered Topologies Directed by Ribbons of Self-Complementary Amide···Amide Ring Motifs in [EDT-TTF-(CONH₂)₂]₂X (X = HSO₄^-, ClO₄^-, ReO₄^-, AsF₆^-):  Coupled Activation of Ribbon Curvature, Electron Interactions, and Magnetic Susceptibility

  摘要：

  The deliberate design of a series of single crystals of conducting two-dimensional radical cation salts of o-bis(amide)-appended ethylenedithiotetrathiafulvalene, beta'-[EDT-TTF-(CONH2)(2)](2)X (X = HSO4-, CLO4-, ReO4-, or AsF6-) and of their parent monocomponent solid EDT-TTF-(CONH2)2 is demonstrated and allows us to reach a level of prediction of the structure of molecular conductors. Their conductivity is activated with a gap of 1650 K and a sizable room-temperature conductivity of 0.15 S-cm(-1) (for X = ClO4-) and a singular spin susceptibility for a beta'-type salt that, in addition, changes very remarkably with the anion. The key design element is that of a recurrent, puckered ribbon constructed out of self-complementary, hydrogen-bonded amide(...)amide ring motifs whose minute modulations of curvature and shape throughout the series have been shown to correlate to very remarkable differences in the intrastack beta(HOMO-HOMO) interaction energies and changes in the density of states at the Fermi level and on to important differences of spin susceptibility behavior in a system where electron correlations are significant. The coupled activation of structure, electron interactions, and magnetic susceptibility discovered and discussed throughout the paper is unprecedented and is seen as a genuine expression of interfacial hydrogen-bond interactions onto the collective electronic properties.

  DOI：

  10.1021/ja0356129
• 作为产物：
  描述：

  ethylenedithio-4',5'-dimethyltetrathiafulvalene-4',5'-dicarboxylate 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以73%的产率得到4,5-ethylenedithio-4',5'-dicarbamoyltetrathiafulvalene
  参考文献：
  名称：

  Singular Crystalline β‘-Layered Topologies Directed by Ribbons of Self-Complementary Amide···Amide Ring Motifs in [EDT-TTF-(CONH₂)₂]₂X (X = HSO₄^-, ClO₄^-, ReO₄^-, AsF₆^-):  Coupled Activation of Ribbon Curvature, Electron Interactions, and Magnetic Susceptibility

  摘要：

  The deliberate design of a series of single crystals of conducting two-dimensional radical cation salts of o-bis(amide)-appended ethylenedithiotetrathiafulvalene, beta'-[EDT-TTF-(CONH2)(2)](2)X (X = HSO4-, CLO4-, ReO4-, or AsF6-) and of their parent monocomponent solid EDT-TTF-(CONH2)2 is demonstrated and allows us to reach a level of prediction of the structure of molecular conductors. Their conductivity is activated with a gap of 1650 K and a sizable room-temperature conductivity of 0.15 S-cm(-1) (for X = ClO4-) and a singular spin susceptibility for a beta'-type salt that, in addition, changes very remarkably with the anion. The key design element is that of a recurrent, puckered ribbon constructed out of self-complementary, hydrogen-bonded amide(...)amide ring motifs whose minute modulations of curvature and shape throughout the series have been shown to correlate to very remarkable differences in the intrastack beta(HOMO-HOMO) interaction energies and changes in the density of states at the Fermi level and on to important differences of spin susceptibility behavior in a system where electron correlations are significant. The coupled activation of structure, electron interactions, and magnetic susceptibility discovered and discussed throughout the paper is unprecedented and is seen as a genuine expression of interfacial hydrogen-bond interactions onto the collective electronic properties.

  DOI：

  10.1021/ja0356129