5-(dimethylamino)methylideneamino-1-(p-chlorophenyl)imidazole-4-carbonitrile | 429675-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(dimethylamino)methylideneamino-1-(p-chlorophenyl)imidazole-4-carbonitrile
• CAS: 429675-69-4
• 化学式: C₁₃H₁₂ClN₅
• 分子量: 273.725
• InChiKey: QOWLLNQAOZZZQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.21
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-(dimethylamino)methylideneamino-1-(p-chlorophenyl)imidazole-4-carbonitrile 在 盐酸 、 sodium hydroxide 、 一水合肼 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 57.0h， 生成 3-(5-amino-1-(p-chlorophenyl)imidazol-4-yl)-1,2,4-triazole
  参考文献：
  名称：

  Basyouni, W. M.; Hosni, Hanaa M., Egyptian Journal of Chemistry, 2001, vol. 44, # 4-6, p. 251 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 1-(p-chlorophenyl)-5-aminoimidazole-4-carboxamide 在 三氯氧磷 作用下， 反应 2.25h， 生成 5-(dimethylamino)methylideneamino-1-(p-chlorophenyl)imidazole-4-carbonitrile
  参考文献：
  名称：

  Studies on complex π-π and T-stacking features of imidazole and phenyl/p-halophenyl units in series of 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides and their carbonitrile derivatives: Role of halogens in tuning of conformation

  摘要：

  5-amino-1-(phenyl/p-halophenyl)imidazole-4-carboxamides (N-phenyl AICA) (2a-e) and 5-amino-1-(phenyl/p-halophenyl)imidazole-4-carbonitriles (N-phenyl AICN) (3a-e) had been synthesized. X-ray crystallographic studies of 2a-e and 3a-e had been performed to identify any distinct change in stacking patterns in their crystal lattice. Single crystal X-ray diffraction studies of 2a-e revealed pi-pi stack formations with both imidazole and phenyl/p-halophenyl units in anti and syn parallel-displaced (PD)-type dispositions. No pi-pi stacking of imidazole occurred when the halogen substituent is bromo or iodo; pi-pi stacking in these cases occurred involving phenyl rings only. The presence of an additional T-stacking had been observed in crystal lattices of 3a-e. Vertical pi-pi stacking distances in anti-parallel PD-type arrangements as well as T-stacking distances had shown stacking distances short enough to impart stabilization whereas syn-parallel stacking arrangements had got much larger pi-pi stacking distances to belie any syn-parallel stacking stabilization. DFT studies had been pursued for quantifying the pi-pi stacking and T-stacking stabilization. The plotted curves for anti-parallel and T-stacked moieties had similarities to the 'Morse potential energy curve for diatomic molecule'. The minima of the curves corresponded to the most stable stacking distances and related energy values indicated stacking stabilization. Similar DFT studies on syn-parallel systems of 2b corresponded to no pi-pi stacking stabilization at all. Halogen-halogen interactions had also been observed to stabilize the compounds 2d, 2e and 3d. Nano-structural behaviour of the series of compounds 2a-e and 3a-e were thoroughly investigated. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2017.06.124