1-(p-chlorophenyl)-5-aminoimidazole-4-carboxamide | 93270-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(p-chlorophenyl)-5-aminoimidazole-4-carboxamide
• 英文别名: 5-amino-1-(p-chlorophenyl)imidazole-4-carboxamide；5-amino-1-(4-chlorophenyl)imidazole-4-carboxamide
• CAS: 93270-68-9
• 化学式: C₁₀H₉ClN₄O
• 分子量: 236.661
• InChiKey: JWSMVUJJDPQXPH-UHFFFAOYSA-N

物化性质

• 熔点：
  262-263 °C
• 沸点：
  483.8±35.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(p-chlorophenyl)-5-aminoimidazole-4-carboxamide 在 盐酸 、 一水合肼 、 三氟乙酸 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 7-(p-chlorophenyl)-1,2,4-triazolo[3,4-i]purine
  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：

  2-氰基-2-(乙氧基亚甲基氨基)乙酰胺 、 对氯苯胺 反应 0.5h， 以67.68%的产率得到1-(p-chlorophenyl)-5-aminoimidazole-4-carboxamide
  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

文献信息

• El-Bayouki, Khairy A. M.; El-Sayed, Ali S.; Basyouni, Whaid M., Gazzetta Chimica Italiana, 1989, vol. 119, # 3, p. 163 - 166
  作者：El-Bayouki, Khairy A. M.、El-Sayed, Ali S.、Basyouni, Whaid M.

  DOI：——

  日期：——
• Chattopadhyay, Gautam; Saha, Tapas K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 4, p. 827 - 830
  作者：Chattopadhyay, Gautam、Saha, Tapas K.

  DOI：——

  日期：——
• EL-BAYOUKI, KHAIRY A. M.;HAMMAD, M.;OSMAN, S. A.;BASYOUNI, W. M., EGYPT. J. CHEM., 29,(1986) N, C. 581-589
  作者：EL-BAYOUKI, KHAIRY A. M.、HAMMAD, M.、OSMAN, S. A.、BASYOUNI, W. M.

  DOI：——

  日期：——
• EL-BAYOUKI KHAIRY A. M.; HAMMAD M.; OSMAN S. A.; BASYOUNI W. M., ORIENT. J. CHEM., 2,(1986) N 1, 45-50
  作者：EL-BAYOUKI KHAIRY A. M.、 HAMMAD M.、 OSMAN S. A.、 BASYOUNI W. M.

  DOI：——

  日期：——
• 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
  作者：Aniruddha Das

  DOI：10.1016/j.molstruc.2017.06.124

  日期：2017.11

  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.