2-(1H-benzo[d]imidazo-2-yl)-4-methylquinoline | 64819-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(1H-benzo[d]imidazo-2-yl)-4-methylquinoline
• 英文别名: 2-(1H-benzoimidazol-2-yl)-4-methyl-quinoline；2-(1H-benzimidazol-2-yl)-4-methylquinoline
• CAS: 64819-83-6
• 化学式: C₁₇H₁₃N₃
• 分子量: 259.31
• InChiKey: ULFOYAKNTRKJII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1H-benzo[d]imidazo-2-yl)-4-methylquinoline 、 碘甲烷 在 potassium tert-butylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到4-methyl-2-(1-methyl-1H-benzo[d]imidazo-2-yl)-quinoline
  参考文献：
  名称：

  Photophysical properties and computational investigations of tricarbonylrhenium(I)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]L and tricarbonylrhenium(I)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]L derivatives (X=N–CH3, O, or S; L=Cl−, pyridine)

  摘要：

  We report a combined experimental and computational study of new rhenium tricarbonyl complexes based on the bidentate heterocyclic N-N ligands 2-(4-methylpyridin-2-yl)benzo[d]-X-azole (X = N-CH3, O, or S) and 2-(benzo[d]-X-azol-2-yl)-4-methylquinoline (X = N-CH3, O, or S). Two sets of complexes are reported. Chloro complexes, described by the general formula Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]Cl (X = N-CH3, 1; X = 0, 2; X = S, 3) and Re(CO)3[2-(benzo[c -X-azol-2-yl)-4-methylquinoline]Cl (X = N-CH3, 4; X = O, 5; X = S, 6) were synthesized heating at reflux Re(CO)(5)Cl with the appropriate N-N ligand in toluene. The corresponding pyridine set {Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo-X-azole]py}PF6 (X = N-CH3, 7; X = O, 8; X = S, 9) and (Re(CO)(3)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]py)PF6(X = N-CH3, 10; X = O, 11; X = S, 12) was synthesized by halide abstraction with silver nitrate of 1-6 followed by heating in pyridine and isolated as their hexafluorophosphate salts. All complexes have been fully characterized by IR, NMR, electrochemical techniques and luminescence. The crystal structures of I and 7 were obtained by X-ray diffraction. DFT and time-dependent (TD) DFT calculations were carried out for investigating the effect of the organic ligand on the optical properties and electronic structure of the reported complexes. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.11.004

文献信息

• Photophysical properties and computational investigations of tricarbonylrhenium(I)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]L and tricarbonylrhenium(I)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]L derivatives (X=N–CH3, O, or S; L=Cl−, pyridine)
  作者：Andrea Albertino、Claudio Garino、Simona Ghiani、Roberto Gobetto、Carlo Nervi、Luca Salassa、Edward Rosenberg、Ayesha Sharmin、Guido Viscardi、Roberto Buscaino、Gianluca Croce、Marco Milanesio

  DOI：10.1016/j.jorganchem.2006.11.004

  日期：2007.2

  We report a combined experimental and computational study of new rhenium tricarbonyl complexes based on the bidentate heterocyclic N-N ligands 2-(4-methylpyridin-2-yl)benzo[d]-X-azole (X = N-CH3, O, or S) and 2-(benzo[d]-X-azol-2-yl)-4-methylquinoline (X = N-CH3, O, or S). Two sets of complexes are reported. Chloro complexes, described by the general formula Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]Cl (X = N-CH3, 1; X = 0, 2; X = S, 3) and Re(CO)3[2-(benzo[c -X-azol-2-yl)-4-methylquinoline]Cl (X = N-CH3, 4; X = O, 5; X = S, 6) were synthesized heating at reflux Re(CO)(5)Cl with the appropriate N-N ligand in toluene. The corresponding pyridine set Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo-X-azole]py}PF6 (X = N-CH3, 7; X = O, 8; X = S, 9) and (Re(CO)(3)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]py)PF6(X = N-CH3, 10; X = O, 11; X = S, 12) was synthesized by halide abstraction with silver nitrate of 1-6 followed by heating in pyridine and isolated as their hexafluorophosphate salts. All complexes have been fully characterized by IR, NMR, electrochemical techniques and luminescence. The crystal structures of I and 7 were obtained by X-ray diffraction. DFT and time-dependent (TD) DFT calculations were carried out for investigating the effect of the organic ligand on the optical properties and electronic structure of the reported complexes. (C) 2006 Elsevier B.V. All rights reserved.