2-N-morpholino-5-isopropyl-1,3-dithiolium-4-thiolate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-N-morpholino-5-isopropyl-1,3-dithiolium-4-thiolate
• 英文别名: 2-Morpholin-4-yl-5-propan-2-yl-1lambda4,3-dithiacyclopenta-1,5-diene-4-thione；2-morpholin-4-yl-5-propan-2-yl-1λ4,3-dithiacyclopenta-1,5-diene-4-thione
• 化学式: C₁₀H₁₅NOS₃
• 分子量: 261.433
• InChiKey: HVTBCJNOFWWXED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  triethylammonium morpholinodithiocarbamate 在 二硫化碳 、 乙酸酐 、 三乙胺 作用下， 以 Petroleum ether 、 苯 为溶剂， 生成 2-N-morpholino-5-isopropyl-1,3-dithiolium-4-thiolate
  参考文献：
  名称：

  MESOIONIC 2-N-CYCLOALKYLAMINO-5-ALKYL-1,3-DITHIOLIUM-4-THIOLATES

  摘要：

  Seven 2-(N-cycloalkylamino-1,3-dithiocarbamoyl)-carboxylic acids and seven mesoionic 2-N-cycloalkylamino-5-alkyl-1,3-dithiolium-4-thiolates have been conveniently synthesized. They were characterized by elemental analysis, I.R., U.V., mass and H-1 NMR spectrometry, plus C-13 NMR spectrometry in some cases. Important questions concerning the structure of the mesoionic compounds, relevant to mesoionic compounds in general, are addressed. In particular, we refer to the degree of separation of regions of positive and negative charge, bond orders, electron and charge delocalization and aromaticity. In this discussion we cite some of our X-ray diffraction and theoretical studies. We conclude that there are regions of positive and negative charge in which there is delocalization of electrons and charge with bond orders between 1 and 2. However, the shared regions are separated by what are essentially single bonds. Thus, they, and mesoionic compounds in general, should not be considered as formally aromatic. This is supported by estimates of Bird Aromaticity indices-experimentally based for two of the title mesoionic compounds-of the order of 50: substantially less than values for thiophene and pyrrole and much less than values for benzene and pyridine. Finally, based on this discussion, we introduce a new notation for the structures of mesoionic compounds which we believe more accurately represents both the bonding situation and the chemical patterns of reactivity of such compounds.

  DOI：

  10.1080/10426509608029640