N,N'-bis((N-picolylbenzimidazol-2-yl)methyl)hexanediamide | 1336918-43-4

• 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((N-picolylbenzimidazol-2-yl)methyl)hexanediamide
• 英文别名: N,N'-bis((1-pyridine-2-ylmethylbenzimidazol-2-yl)methyl)hexane-1,6-diamide；Pic-GBHA；N,N'-bis[[1-(pyridin-2-ylmethyl)benzimidazol-2-yl]methyl]hexanediamide
• CAS: 1336918-43-4
• 化学式: C₃₄H₃₄N₈O₂
• 分子量: 586.696
• InChiKey: YTMFMVMIIRECCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 N,N'-bis((N-picolylbenzimidazol-2-yl)methyl)hexanediamide 以 甲醇 为溶剂， 以85%的产率得到dichloro(N,N'-bis((N-picolylbenzimidazol-2-yl)methyl)hexanediamide)copper(II) hemihydrate
  参考文献：
  名称：

  Copper(II) complexes of a new N-picolylated bis benzimidazolyl diamide ligand: Synthesis, crystal structure and catechol oxidase studies

  摘要：

  Copper(II) complexes of a new bis benzimidazole diamide ligand N-picolyl-N,N'-bis(2-methylbenzimidazolyl) hexanediamide [Pic-GBHA = L(2)] have been synthesized and characterized. One of the compound [Cu(L(2))(NO(3))(2)] has been structurally characterized. The copper atom is bound to two benzimidazolyl nitrogen atoms, two amide carbonyl oxygen atoms and a bidentate nitrate ion, resulting in a distorted octahedral geometry. EPR spectra obtained at low temperature indicate a tetragonal geometry in the solution state. Complexes display a quasi-reversible redox wave due to the Cu(II)/Cu(I) reduction process having fairly cathodic E(1/2). These Cu(II) complexes were utilized to carry out oxidation of ditertbutylcatechol (DTBC) in methanol using molecular oxygen as the oxidant in. Low temperature EPR study of the oxidation reaction implicates the formation of an active copper species with fairly low A(parallel to) value. The presence of picolyl groups on the ligand also serve as a proton sponge giving 2-3 times higher rates of reaction in comparison to the non-picolylated ligand, implying a role of free basic groups in the pH control of enzymatic oxidation of catechols by catechol oxidase and tyrosinase. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.06.013
• 作为产物：
  描述：

  2-氯甲基吡啶 、 N,N'-bis(glycine-2-benzimidazolyl)hexanediamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N,N'-bis((N-picolylbenzimidazol-2-yl)methyl)hexanediamide
  参考文献：
  名称：

  Copper(II) complexes of a new N-picolylated bis benzimidazolyl diamide ligand: Synthesis, crystal structure and catechol oxidase studies

  摘要：

  Copper(II) complexes of a new bis benzimidazole diamide ligand N-picolyl-N,N'-bis(2-methylbenzimidazolyl) hexanediamide [Pic-GBHA = L(2)] have been synthesized and characterized. One of the compound [Cu(L(2))(NO(3))(2)] has been structurally characterized. The copper atom is bound to two benzimidazolyl nitrogen atoms, two amide carbonyl oxygen atoms and a bidentate nitrate ion, resulting in a distorted octahedral geometry. EPR spectra obtained at low temperature indicate a tetragonal geometry in the solution state. Complexes display a quasi-reversible redox wave due to the Cu(II)/Cu(I) reduction process having fairly cathodic E(1/2). These Cu(II) complexes were utilized to carry out oxidation of ditertbutylcatechol (DTBC) in methanol using molecular oxygen as the oxidant in. Low temperature EPR study of the oxidation reaction implicates the formation of an active copper species with fairly low A(parallel to) value. The presence of picolyl groups on the ligand also serve as a proton sponge giving 2-3 times higher rates of reaction in comparison to the non-picolylated ligand, implying a role of free basic groups in the pH control of enzymatic oxidation of catechols by catechol oxidase and tyrosinase. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.06.013

文献信息

• Copper(II) complexes of a new N-picolylated bis benzimidazolyl diamide ligand: Synthesis, crystal structure and catechol oxidase studies
  作者：Ruchi Bakshi、Miriam Rossi、Francesco Caruso、Pavan Mathur

  DOI：10.1016/j.ica.2011.06.013

  日期：2011.10

  Copper(II) complexes of a new bis benzimidazole diamide ligand N-picolyl-N,N'-bis(2-methylbenzimidazolyl) hexanediamide [Pic-GBHA = L(2)] have been synthesized and characterized. One of the compound [Cu(L(2))(NO(3))(2)] has been structurally characterized. The copper atom is bound to two benzimidazolyl nitrogen atoms, two amide carbonyl oxygen atoms and a bidentate nitrate ion, resulting in a distorted octahedral geometry. EPR spectra obtained at low temperature indicate a tetragonal geometry in the solution state. Complexes display a quasi-reversible redox wave due to the Cu(II)/Cu(I) reduction process having fairly cathodic E(1/2). These Cu(II) complexes were utilized to carry out oxidation of ditertbutylcatechol (DTBC) in methanol using molecular oxygen as the oxidant in. Low temperature EPR study of the oxidation reaction implicates the formation of an active copper species with fairly low A(parallel to) value. The presence of picolyl groups on the ligand also serve as a proton sponge giving 2-3 times higher rates of reaction in comparison to the non-picolylated ligand, implying a role of free basic groups in the pH control of enzymatic oxidation of catechols by catechol oxidase and tyrosinase. (C) 2011 Elsevier B.V. All rights reserved.