2-[Bis(5-methylthiophen-2-yl)methylidene]-5-methylthiophen-1-ium | 133374-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-[Bis(5-methylthiophen-2-yl)methylidene]-5-methylthiophen-1-ium
• CAS: 133374-00-2
• 化学式: C₁₆H₁₅S₃
• 分子量: 303.493
• InChiKey: INEJOTQBGNDZLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-lithio-5-methylthiophene 在 三氟乙酸 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 18.0h， 生成 2-[Bis(5-methylthiophen-2-yl)methylidene]-5-methylthiophen-1-ium
  参考文献：
  名称：

  The tris(2-thienyl)methyl cation problem. NMR spectroscopic study

  摘要：

  A series of homologues of the trityl cation obtained by total or partial substitution of the phenyl rings for 2- or 3-thienyl groups has been studied by H-1 and C-13 NMR. In general, the spectral parameters found follow the expected trends. However, a most unexpected effect is found in the transformation of tris(2-thienyl)carbinol (1d) into tris(2-thienyl)methyl cation (2d), since the increase of the total chemical shift (DELTA-SIGMA-delta) associated with the ionization is as low as 105 ppm. To account for this observation, several hypotheses are discussed including the possibility of through-space charge delocalization by the three sulfur atoms and the interaction of the thiophene rings in an alternate conformation.

  DOI：

  10.1021/jo00010a011

文献信息

• The tris(2-thienyl)methyl cation problem. NMR spectroscopic study
  作者：Belen Abarca、Gregorio Asensio、Rafael Ballesteros、Teresa Varea

  DOI：10.1021/jo00010a011

  日期：1991.5

  A series of homologues of the trityl cation obtained by total or partial substitution of the phenyl rings for 2- or 3-thienyl groups has been studied by H-1 and C-13 NMR. In general, the spectral parameters found follow the expected trends. However, a most unexpected effect is found in the transformation of tris(2-thienyl)carbinol (1d) into tris(2-thienyl)methyl cation (2d), since the increase of the total chemical shift (DELTA-SIGMA-delta) associated with the ionization is as low as 105 ppm. To account for this observation, several hypotheses are discussed including the possibility of through-space charge delocalization by the three sulfur atoms and the interaction of the thiophene rings in an alternate conformation.