1-Ethyl-2-[(E)-(naphthalen-2-yl)diazenyl]-1H-imidazole | 295806-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Ethyl-2-[(E)-(naphthalen-2-yl)diazenyl]-1H-imidazole
• 英文别名: (1-ethylimidazol-2-yl)-naphthalen-2-yldiazene
• CAS: 295806-50-7
• 化学式: C₁₅H₁₄N₄
• 分子量: 250.303
• InChiKey: DLMBILRZGKVFPB-UHFFFAOYSA-N

物化性质

• 沸点：
  441.3±28.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dicarbonyldichlororuthenium 、 1-Ethyl-2-[(E)-(naphthalen-2-yl)diazenyl]-1H-imidazole 以 乙腈 为溶剂， 反应 6.0h， 生成 C₁₇H₁₄Cl₂N₄O₂Ru
  参考文献：
  名称：

  Ru(II)–halide–carbonyl complexes of naphthylazoimidazoles: Synthesis, spectra, electrochemistry, catalytic activity and electronic structure

  摘要：

  [Ru(CO)(2)Cl-2(alpha/beta-NaiR)] (1, 2) and [Ru(CO)(2)I-2(alpha/beta-NaiR)] (3, 4) are synthesized by the reaction of [Ru(CO)(2)Cl-2](n) or [Ru(CO)(4)I-2] with alpha/beta-NaiR (1-alkyl-2-(naphthyl-alpha/beta-azo)imidazole (alpha-NaiR/beta-NaiR, where, R = Me, CH2CH3 and CH2Ph)) and have been characterized by spectroscopic data. The geometry of the representative complexes [Ru(CO)(2)Cl-2(beta-NaiMe)] (2a) and [Ru(CO)(2)I-2(beta-NaiEt)] (4b) have been structurally confirmed by X-ray diffraction study. The redox property is examined by electrochemistry. Catalytic activity of these compounds is investigated to the oxidation of PhCH2OH to PhCHO, 2-butanol (C4H9OH) to 2-butanone, 1-phenylethanol (PhC2H4OH) to acetophenone, cyclopentanol (C5H9OH) to cyclopentanone and cyclohexanol to cyclohexanone by N-methylmorpholine-N-oxide (NMO), H2O2 or (BuOOH)-O-t in CH2Cl2 and NMO shows highest yield. The catalytic efficiency is again dependent on Ru-X (X = Cl or I) bond and higher yield is observed for [Ru(CO)(2)Cl-2(alpha/beta-NaiR)] (1, 2). Electronic structure, spectral and redox properties are explained based on DFT and TD-DFT calculations on the representative complexes. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.06.009

文献信息

• Ru(II)–halide–carbonyl complexes of naphthylazoimidazoles: Synthesis, spectra, electrochemistry, catalytic activity and electronic structure
  作者：Shyamal Kumar Sarkar、Mahendra Sekhar Jana、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.jorganchem.2012.06.009

  日期：2012.10

  [Ru(CO)(2)Cl-2(alpha/beta-NaiR)] (1, 2) and [Ru(CO)(2)I-2(alpha/beta-NaiR)] (3, 4) are synthesized by the reaction of [Ru(CO)(2)Cl-2](n) or [Ru(CO)(4)I-2] with alpha/beta-NaiR (1-alkyl-2-(naphthyl-alpha/beta-azo)imidazole (alpha-NaiR/beta-NaiR, where, R = Me, CH2CH3 and CH2Ph)) and have been characterized by spectroscopic data. The geometry of the representative complexes [Ru(CO)(2)Cl-2(beta-NaiMe)] (2a) and [Ru(CO)(2)I-2(beta-NaiEt)] (4b) have been structurally confirmed by X-ray diffraction study. The redox property is examined by electrochemistry. Catalytic activity of these compounds is investigated to the oxidation of PhCH2OH to PhCHO, 2-butanol (C4H9OH) to 2-butanone, 1-phenylethanol (PhC2H4OH) to acetophenone, cyclopentanol (C5H9OH) to cyclopentanone and cyclohexanol to cyclohexanone by N-methylmorpholine-N-oxide (NMO), H2O2 or (BuOOH)-O-t in CH2Cl2 and NMO shows highest yield. The catalytic efficiency is again dependent on Ru-X (X = Cl or I) bond and higher yield is observed for [Ru(CO)(2)Cl-2(alpha/beta-NaiR)] (1, 2). Electronic structure, spectral and redox properties are explained based on DFT and TD-DFT calculations on the representative complexes. (C) 2012 Elsevier B.V. All rights reserved.