pentakis(1,3-benzodithiol-2-ylidene)cyclopentane | 127025-54-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: pentakis(1,3-benzodithiol-2-ylidene)cyclopentane
• 英文别名: 2-[2,3,4,5-tetrakis(1,3-benzodithiol-2-ylidene)cyclopentylidene]-1,3-benzodithiole
• CAS: 127025-54-1
• 化学式: C₄₀H₂₀S₁₀
• 分子量: 821.259
• InChiKey: XOHSRLVCPIAAJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  50
• 可旋转键数：
  0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  253
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  pentakis(1,3-benzodithiol-2-ylidene)cyclopentane 以 苯甲腈 为溶剂， 生成 2-[2-(1,3-Benzodithiol-3-ium-2-yl)-3,4,5-tris(1,3-benzodithiol-2-ylidene)cyclopenten-1-yl]-1,3-benzodithiol-3-ium
  参考文献：
  名称：

  Oxidation States of [5]Radialene with Five 1,3-Dithiol-2-ylidenes and Its Oxygen Adduct

  摘要：

  对[5]辐射烯与五个 1,3-二硫醇-2-亚基 (DT) (1) 进行了光谱电化学分析。 12+ 的紫外-可见-近红外光谱表明三个 DT 单元上两个正电荷的离域。氧加合物 (2)2+(AsF6−)2(PhCl)1.5 的 X 射线结构分析表明 22+ 在中心五元环中具有环戊二烯化物结构。

  DOI：

  10.1246/cl.130142
• 作为产物：
  描述：

  tetrakis-(1,3-benzodithiol-2-ylidene)cyclopentanone 在 四氟硼酸-二乙醚络合物 、 lithium aluminium tetrahydride 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 6.5h， 生成 pentakis(1,3-benzodithiol-2-ylidene)cyclopentane
  参考文献：
  名称：

  Novel redox behavior of [5]radialenes substituted with 1,3-dithiol groups

  摘要：

  Only one pair of reversible waves involving a net four-electron transfer has been observed in the redox process of pentakis(1,3-benzodithiol-2-ylidene)cyclopentane (1a), a potent electron-donating molecule. This is the first case of a single-wave four-electron transfer with only one macroscopic redox site in organic redox systems. Normal explicit difference digital simulation analysis assuming Nemstian response has been carried out to elucidate the detailed redox process of la. Our studies have shown that la mainly follows a two-step two-electron transfer and is converted to the tetracation (1a4+) via the dication (1a2+). The estimated redox potentials for the 1a/1a2+ and 1a2+/1a4+ couples are 0.394 +/- 0.003 and 0.386 +/- 0.003 V vs SCE, respectively. Thus three electrons are transferred at virtually no cost in energy after the first electron is transferred. The C-13 NMR study has revealed that 1a4+ has a unique electronic structure of cyclopentadienide substituted with five 1,3-dithiolylium groups. Two factors play important roles in the unusual multiple electron transfer with enhanced interaction: (1) preferential twist of all five 1,3-dithiolylium moieties from the central five-membered ring so as to decrease the intramolecular Coulomb repulsion and steric hindrance; (2) the aromatic stabilization arising from the contribution of the cyclopentadienide structure in 1a4+.

  DOI：

  10.1021/j100052a042

文献信息

• Sugimoto, Toyonari; Misaki, Yohji; Yoshida, Zen-Ichi, Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 176, p. 259 - 270
  作者：Sugimoto, Toyonari、Misaki, Yohji、Yoshida, Zen-Ichi、Yamauchi, Jun

  DOI：——

  日期：——