N,N'-bis(1-methylbenzimidazol-2-ylethyl)ethane-1,2-diamine | 145533-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N,N'-bis(1-methylbenzimidazol-2-ylethyl)ethane-1,2-diamine
• 英文别名: N,N'-bis(N-methylbenzimidazol-2-ylethyl)ethylenediamine；N,N'-bis[2-(1-methylbenzimidazol-2-yl)ethyl]ethane-1,2-diamine
• CAS: 145533-45-5
• 化学式: C₂₂H₂₈N₆
• 分子量: 376.505
• InChiKey: PWAUBVKLQLJWOG-UHFFFAOYSA-N

物化性质

• 沸点：
  631.7±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.7
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 N,N'-bis(1-methylbenzimidazol-2-ylethyl)ethane-1,2-diamine 以 甲醇 为溶剂， 生成 Cu(N,N'-bis(1-methylbenzimidazol-2-ylethyl)ethane-1,2-diamine)(ClO4)2
  参考文献：
  名称：

  Structure, spectra and redox behaviour of copper(II) complexes of bis(benzimidazolyl)diamine ligands

  摘要：

  The linear quadridentate ligand N,N'-bis(benzimidazol-2-ylethyl)ethane-1,2-diamine (L1) and its 1-methylbenzimidazole analogue (L2) and homologues form 1:1 complexes with Cu (ClO4)2; L1 also forms complexes of the types CuL1X2 where X = NO3, PF6, Br or Cl and CuL1(X)Y where X = Cl or Br and Y = ClO4 or Br. Deep blue CuL1Br2.2H2O crystallizes in the monoclinic space group C2/c with Z = 4, a = 9.919(2), b = 16.626(3), c = 14.102(3) angstrom and beta = 94.39(2)-degrees. The structure was solved by Patterson and Fourier difference methods and refined by the least-squares technique to R = 0.064 for 2195 independent reflections with / > 1.5sigma(/). The molecule lies on a two-fold axis symmetrically around Cu(II). The co-ordination around Cu(II) is found to be square planar with two amino nitrogens and two benzimidazole nitrogens forming the equatorial plane [Cu-N 1.983(3) and 2.037(4) angstrom]. The bromides are at longer distances [3.349(1) angstrom] in axial sites. Ligand field and EPR spectra indicate that one bromide or chloride ion is axially co-ordinated to Cu(II) in [CuL1]2+. This ion exhibits quasi-reversible redox behaviour. Electrochemical studies of the dihalides in methanol have established the presence of [CuL1X2], [CuL1(X)]+ and [CuL1]2+ in equilibrium. In complexes with 565 [CuL4]2+ [L4 = N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine] and 555 [CuL3]2+ [L3 = N,N'-bis(1-methylbenzimidazol-2-ylmethyl)propane-1,3-diamine] chelate rings, Cu(II) does not seem to lie in the N4 square plane, as revealed by their low A(parallel-to) values and irreversible electrochemical behaviour. The Cu(II)-Cu(I) redox potentials in methanol are in the order [CuL1]2+ < [CuL3]2+ < [CuL4]2+; this illustrates that six-membered chelate rings are suitable to stabilize Cu(II), when Cu-N sigma interactions are favourable.

  DOI：

  10.1039/dt9920003377
• 作为产物：
  描述：

  3,3'-(1,2-乙二基二亚氨基)二丙酰胺 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 N,N'-bis(1-methylbenzimidazol-2-ylethyl)ethane-1,2-diamine
  参考文献：
  名称：

  Sivagnanam, Usha; Pandiyan, Thangarasu; Palaniandavar, Mallayan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 5, p. 572 - 576

  摘要：

  DOI：