3,4,5,6-四氯-N-己基邻苯二甲酰亚胺 | 14737-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 3,4,5,6-四氯-N-己基邻苯二甲酰亚胺
• 英文名称: N-n-hexyltetrachlorophthalimide
• 英文别名: 1H-Isoindole-1,3(2H)-dione, 4,5,6,7-tetrachloro-2-hexyl-；4,5,6,7-tetrachloro-2-hexylisoindole-1,3-dione
• CAS: 14737-86-1
• 化学式: C₁₄H₁₃Cl₄NO₂
• 分子量: 369.075
• InChiKey: PVYDPFXQCMGQTK-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  477.5±45.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2925190090

反应信息

• 作为产物：
  描述：

  正己胺 、 四氯苯二甲酸酐 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到3,4,5,6-四氯-N-己基邻苯二甲酰亚胺
  参考文献：
  名称：

  Spectroscopic properties of N-n-butyltetrachlorophthalimide and supramolecular interactions in its crystals

  摘要：

  A number of N-n-alkyltetrachlorophthalimides has been synthesized and N-n-butyltetrachlorophthalimide has been characterized by X-ray diffraction, FT-IR and NMR spectroscopy. Also B3LYP and DFT calculations have been carried out. The optimized bond lengths, bond angles and torsion angles calculated by B3LYP/6-31G(d,p) approach have been compared with the X-ray data. The screening constants for 13 C and 1 H atoms have been calculated by the GIAO/B3LYP/6-31 G(d,p) approach and analyzed. Linear correlations between the experimental 1(H) and C-13 chemical shifts and the computed screening constants have been obtained which confirm the optimized geometry. In the supramolecular structure halogen bonds and intermolecular Cl...Cl interactions have been found as the main driving force which connects molecules into centrosymmetric tapes and planar sheets. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2006.10.002

文献信息

• Allen; Nicholls, Journal of the American Chemical Society, 1934, vol. 56, p. 1410
  作者：Allen、Nicholls

  DOI：——

  日期：——
• Spectroscopic properties of N-n-butyltetrachlorophthalimide and supramolecular interactions in its crystals
  作者：Teresa Borowiak、Irena Wolska、Bogumił Brycki、Andrzej Zieliński、Iwona Kowalczyk

  DOI：10.1016/j.molstruc.2006.10.002

  日期：2007.5

  A number of N-n-alkyltetrachlorophthalimides has been synthesized and N-n-butyltetrachlorophthalimide has been characterized by X-ray diffraction, FT-IR and NMR spectroscopy. Also B3LYP and DFT calculations have been carried out. The optimized bond lengths, bond angles and torsion angles calculated by B3LYP/6-31G(d,p) approach have been compared with the X-ray data. The screening constants for 13 C and 1 H atoms have been calculated by the GIAO/B3LYP/6-31 G(d,p) approach and analyzed. Linear correlations between the experimental 1(H) and C-13 chemical shifts and the computed screening constants have been obtained which confirm the optimized geometry. In the supramolecular structure halogen bonds and intermolecular Cl...Cl interactions have been found as the main driving force which connects molecules into centrosymmetric tapes and planar sheets. (c) 2006 Elsevier B.V. All rights reserved.
• Spectroscopic properties of N-n-hexyltetrachlorophthalimide and supramolecular interactions in its crystals
  作者：Bogumił Brycki、Iwona Kowalczyk、Andrzej Zieliński、Teresa Borowiak、Irena Wolska

  DOI：10.1016/j.molstruc.2007.03.046

  日期：2008.2

  N-n-hexyltetrachlorophthalimide has been characterized by X-ray diffraction, FTIR, Raman and NMR spectroscopy. Also B3LYP and DFT calculations have been carried out. The optimized bond lengths, bond angles and torsion angles calculated by B3LYP/6-31G(d,p) approach have been compared with the X-ray data. The screening constants for C-13 and H-1 atoms have been calculated by the GIAO/B3LYP/6-31G(d,p) approach and analyzed. Linear correlations between the experimental 1H and 13C chemical shifts and the computed screening constants confirm the optimized geometry. The supramolecular structure is organized into hydrophilic and hydrophobic segments. The tetrachlorophthalimide moieties of the hydrophilic segments form infinite chains via halogen bonds C=O center dot center dot center dot Cl. These bonds as well as weak intermolecular hydrogen bonds C-H center dot center dot center dot O contribute to the parallel orientation of the chains and to the stabilization of their flat conformation. The intermolecular Cl center dot center dot center dot Cl interactions stabilize the organization of the hydrophilic segments. (c) 2007 Elsevier B.V. All rights reserved.