bis(N-cyclobutylimino)-1,4-dithiin | 1485383-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: bis(N-cyclobutylimino)-1,4-dithiin
• 英文别名: 5,11-Di(cyclobutyl)-2,8-dithia-5,11-diazatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-diene-4,6,10,12-tetrone；5,11-di(cyclobutyl)-2,8-dithia-5,11-diazatricyclo[7.3.0.03,7]dodeca-1(9),3(7)-diene-4,6,10,12-tetrone
• CAS: 1485383-87-6
• 化学式: C₁₆H₁₄N₂O₄S₂
• 分子量: 362.43
• InChiKey: FPQKWHCOTYISFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-甲基蒽 、 bis(N-cyclobutylimino)-1,4-dithiin 以 氯仿 为溶剂， 生成 C₃₁H₂₈N₂O₄S₂
  参考文献：
  名称：

  Cooperativity and Feedback Mechanisms in the Single-Crystal-to-Single-Crystal Solid-State Diels–Alder Reaction of 9-Methylanthracene with Bis(N-cyclobutylimino)-1,4-dithiin

  摘要：

  Electron donor-to-acceptor interactions between 9-methylanthracene and bis(N-cyclobutylimino)-1,4-dithiin lead to the formation of chiral charge-transfer (CT) crystals. The structure consists of charge-transfer stacks where these two molecules arrange in a 1:1 alternating arrangement. These undergo a topochemical thermal single-crystal-to-single-crystal (SCSC) [2 + 4] Diels-Alder reaction in the solid state. CT crystals were reacted at 40 degrees C, their structures were determined by X-ray diffraction at various degrees of conversion, and they were examined using Hirshfeld surfaces and lattice energy calculations to find evidence of reaction cooperativity and feedback mechanisms. The results show that steric effects between product molecules and reactant molecules during the SCSC reaction influence the formation of products along the b axis, resulting in a more ordered structure than initially suggested by the crystal structure analysis. A maximum reaction conversion of around 96% was obtained, which indicates that the reaction is also nonrandom within the charge-transfer stacks. Lattice and intramolecular energy calculations show that the energy of an inherently metastable crystal obtained via the SCSC reaction is slightly higher compared to that of the recrystallized product crystal. Finally, structural analysis using CrystalExplorer shows that the shape, size, and surface curvature of the Hirshfeld surface are not much changed by the reaction, indicating that the reaction cavity remains relatively constant and that the reaction is under topochemical control.

  DOI：

  10.1021/cg401474f
• 作为产物：
  描述：

  丁二酸酐 、 氯化亚砜 、 环丁基胺 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以14%的产率得到bis(N-cyclobutylimino)-1,4-dithiin
  参考文献：
  名称：

  Cooperativity and Feedback Mechanisms in the Single-Crystal-to-Single-Crystal Solid-State Diels–Alder Reaction of 9-Methylanthracene with Bis(N-cyclobutylimino)-1,4-dithiin

  摘要：

  Electron donor-to-acceptor interactions between 9-methylanthracene and bis(N-cyclobutylimino)-1,4-dithiin lead to the formation of chiral charge-transfer (CT) crystals. The structure consists of charge-transfer stacks where these two molecules arrange in a 1:1 alternating arrangement. These undergo a topochemical thermal single-crystal-to-single-crystal (SCSC) [2 + 4] Diels-Alder reaction in the solid state. CT crystals were reacted at 40 degrees C, their structures were determined by X-ray diffraction at various degrees of conversion, and they were examined using Hirshfeld surfaces and lattice energy calculations to find evidence of reaction cooperativity and feedback mechanisms. The results show that steric effects between product molecules and reactant molecules during the SCSC reaction influence the formation of products along the b axis, resulting in a more ordered structure than initially suggested by the crystal structure analysis. A maximum reaction conversion of around 96% was obtained, which indicates that the reaction is also nonrandom within the charge-transfer stacks. Lattice and intramolecular energy calculations show that the energy of an inherently metastable crystal obtained via the SCSC reaction is slightly higher compared to that of the recrystallized product crystal. Finally, structural analysis using CrystalExplorer shows that the shape, size, and surface curvature of the Hirshfeld surface are not much changed by the reaction, indicating that the reaction cavity remains relatively constant and that the reaction is under topochemical control.

  DOI：

  10.1021/cg401474f

文献信息

• A synthetic co-crystal prepared by cooperative single-crystal-to-single-crystal solid-state Diels–Alder reaction
  作者：S. Khorasani、M. A. Fernandes

  DOI：10.1039/c6cc07628a

  日期：——

  Solid-state Diels–Alder reaction in a 2 : 1 donor to acceptor charge-transfer complex leads to a synthetic co-crystal composed of product and unreacted donor. Analysis of close contacts and DFT energy calculations indicate that the reaction occurs cooperatively where the arrangement of molecules shown in (ii) is favoured.

  在一个2:1的供体到受体电荷转移复合物中，固态Diels-Alder反应导致合成了一个由产物和未反应的供体组成的合成共晶。接近接触的分析和DFT能量计算表明，反应是协同发生的，其中(ii)所示的分子排列方式更有利。