1-Methyl-2-(p-nitro-phenylazo)-imidazol | 72908-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Methyl-2-(p-nitro-phenylazo)-imidazol
• 英文别名: N(1)-methyl-2-(4'-nitrophenylazo)imidazole；1-methyl-2-(4'-nitrophenylazo)imidazole；1-methyl-2-(4-nitro-phenylazo)-1H-imidazole；(1-Methylimidazol-2-yl)-(4-nitrophenyl)diazene
• CAS: 72908-94-2
• 化学式: C₁₀H₉N₅O₂
• 分子量: 231.214
• InChiKey: UAMJLCNBORLNRB-UHFFFAOYSA-N

物化性质

• 熔点：
  192 °C
• 沸点：
  434.3±47.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  88.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0) 、 1-Methyl-2-(p-nitro-phenylazo)-imidazol 以 二氯甲烷 为溶剂， 以75%的产率得到cis-tetracarbonyl(N(1)-methyl-2-(4'-nitrophenylazo)imidazole)
  参考文献：
  名称：

  Synthesis and characterization of cis-Mo(CO)4(L–L′) and cis-Mo(CO)2(L–L′)2 complexes of N(1)-methyl-2-(arylazo)imidazoles (L–L′). Correlations of spectroscopic data with substituent effects

  摘要：

  N(1)-Methyl-2-(p-X-phenylazo)imidazoles (L-L'; X = CH3O, CH3, H, Br, CF3, NO2) react with cis -(norbornadiene)MO(CO)(4) and MO(CO)(3)(CH3CN)(3) to provide the complexes CiS-MO(CO)(4)(L-L) (X = CH3O, CH3, H, Br, CF3, NO2) and CiS-MO(CO)(2)(L-L')(2) (X = CH3, H, Br, CF3), respectively. The complexes were characterized by visible and infrared spectroscopy, by H-1-, C-13- and Mo-95-NMR spectroscopy, and by cyclic voltammetry. Correlations among the data and correlations of the data with the Hammett sigma parameter within each set of complexes were investigated and are generally very good. These data, as well as the inability to synthesize complexes of the type Mo(L-L')(3), indicate that 2-(arylazo)imidazoles are less effective ligands at stabilizing complexes of zerovalent metals than are 2-(arylazo)pyridines. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00793-9

文献信息

• Bag; Misra; Sinha, Journal of the Indian Chemical Society, 1998, vol. 75, # 7, p. 421 - 422
  作者：Bag、Misra、Sinha

  DOI：——

  日期：——
• Chemistry of Azoimidazoles: Synthesis, Spectral Characterization, Electrochemical Studies, and X-ray Crystal Structures of Isomeric Dichloro Bis[1-alkyl-2-(arylazo)imidazole] Complexes of Ruthenium(II)
  作者：Tarun Kumar Misra、Debasis Das、Chittaranjan Sinha、Ghosh、Chandan Kumar Pal

  DOI：10.1021/ic970446p

  日期：1998.4.20

  Several new ligands, azoimidazoles belonging to the class 1-methyl-2-(arylazo)imidazoles (L-1 (3)) and 1-benzyl 2-(arylazo)imidazoles (L-2 (4)) (R = H (a), Me (b), OMe (c), Cl (d), NO2 (e)) have been synthesized and reacted with RuCl3 in ethanol under refluxing conditions. Two isomers of the composition RuL2Cl2, green (i) and blue (iii): are chromatographically separated. The green isomer is quantitatively transformed to the blue isomer on refluxing in a high boiling solvent. The isomeric structures have been confirmed by X-ray crystallography. Crystal data are as follows. Green complex C38H34Cl2N8Ru (6a): crystal system monoclinic; space group C2/c; a 15.650(8) Angstrom; b = 22.766(14) Angstrom: c = 11.473(5) Angstrom: beta = 119.27(4)degrees; V = 3573(3) Angstrom(3) Z = 4; R = 3.59%; R-w = 4.38%. Blue complex C22H24Cl2N8Ru(7b): crystal system monoclinic; space group P2(1)/n, a = 9.547(6) Angstrom; b = 22.554(14) Angstrom; c = 11.745(8) Angstrom: beta = 99.07(5)degrees; V = 2498(3) Angstrom(3); Z = 4; R = 3.15%; R-w = 4.51%. With reference to the pairs of Cl, N(imidazole), and N(azo) bound to Ru, the green isomer (6a) has a trans-cis-cis configuration and the blue isomer (7b) is cis-trans-cis. In both structures the Ru-N(azo) distances are relatively shorter than Ru-N(imidazole). indicating stronger bonding in the former and the presence of a Ru-L pi-interaction that is localized in the Ru-azo fragment. The isomer configuration is supported by IR and H-1 NMR data. The compounds exhibit t(2)(Ru) --> pi*(L) MLCT transitions in the visible region. Redox studies show the Ru(TLI)/Ru(II) couple in the green complexes (5, 6) at 0.6-0.7 V and in the blue complexes at 0.7-0.8 V versus SCE and two successive e azo reductions. The difference in the first metal and ligand redox potentials is linearly correlated with nu(CT) (t(2)(Ru) --> pi*(L).