2,6-diaminopyrazine-3,5-bisthiocyanate | 881845-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,6-diaminopyrazine-3,5-bisthiocyanate
• 英文别名: (3,5-Diamino-6-thiocyanatopyrazin-2-yl) thiocyanate
• CAS: 881845-69-8
• 化学式: C₆H₄N₆S₂
• 分子量: 224.27
• InChiKey: FNIFCFRNIIEASU-UHFFFAOYSA-N

物化性质

• 沸点：
  461.8±45.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-diaminopyrazine-3,5-bisthiocyanate 、 三丁基膦 以 水 为溶剂， 生成 2-tributylphosphinimino-6-aminopyrazine-3,5-dithiol
  参考文献：
  名称：

  Bimodal association of a bis-1,2,3-dithiazolyl radical

  摘要：

  N- 乙基吡嗪键合的双-1,2,3-二噻唑基 2（R1 = Et）在室温下以 C-C 键合的σ-二聚体形式结合，加热后转变为横向的 S-S σ 键合结构。

  DOI：

  10.1039/b517098b
• 作为产物：
  描述：

  硫氰酸铵 、 2,6-二氨基吡嗪 在 溴 作用下， 生成 2,6-diaminopyrazine-3,5-bisthiocyanate
  参考文献：
  名称：

  Bimodal association of a bis-1,2,3-dithiazolyl radical

  摘要：

  N- 乙基吡嗪键合的双-1,2,3-二噻唑基 2（R1 = Et）在室温下以 C-C 键合的σ-二聚体形式结合，加热后转变为横向的 S-S σ 键合结构。

  DOI：

  10.1039/b517098b

文献信息

• An Alternating π-Stacked Bisdithiazolyl Radical Conductor
  作者：Alicea A. Leitch、Robert W. Reed、Craig M. Robertson、James F. Britten、Xueyang Yu、Richard A. Secco、Richard T. Oakley

  DOI：10.1021/ja071218p

  日期：2007.6.1

  A general synthetic route to the resonance-stabilized pyrazine-bridged bisdithiazolyl framework, involving the reductive deprotection of 2,6-diaminopyrazine-bisthiocyanate and cyclization with thionyl chloride, has been developed. An N-methyl bisdithiazolyl radical, 4-methyl-4H-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyrazin-3-yl, has been prepared and characterized in solution by electron paramagnetic resonance spectroscopy and cyclic voltammetry. Its crystal structure has been determined at several temperatures. At 295 K, the structure belongs to the space group Cmca and consists of evenly spaced radicals pi-stacked in an alternating ABABAB fashion along the x-direction. At 123 K, the space group symmetry is lowered by loss of C-centering to Pccn, so that the radicals are no longer evenly spaced along the pi-stack. At 88 K, a further lowering of space group symmetry to P2(1)/c is observed. Extended Huckel Theory band structure calculations indicate a progressive opening of a band gap at the Fermi level in the low-temperature structures. Magnetic susceptibility measurements over the range 4-300 K reveal essentially diamagnetic behavior below 120 K. Variable-temperature single-crystal conductivity (sigma) measurements indicate that the conductivity is activated, even at room temperature, with a room-temperature value sigma(RT) = 0.001 S cm(-1) and a thermal activation energy E-act = 0.19 eV. Under an applied pressure of 5 GPa, sigma(RT) is increased by 3 orders of magnitude, but the conductivity remains activated, with E-act being lowered to 0.11 eV at 5.5 GPa.