1-ethyl-2-(phenylazo)imidazole | 198347-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-ethyl-2-(phenylazo)imidazole
• 英文别名: 1-(Ethyl)-2-(phenylazo)imidazole；(1-ethylimidazol-2-yl)-phenyldiazene
• CAS: 198347-69-2
• 化学式: C₁₁H₁₂N₄
• 分子量: 200.243
• InChiKey: RPECJHRXDVSBLM-UHFFFAOYSA-N

物化性质

• 沸点：
  344.1±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-ethyl-2-(phenylazo)imidazole 在 (C₂H₅)3N 作用下， 以 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 生成 (4-tert-butylcatecholato)(1-ethyl-2-(phenylazo)imidazole)platinum(II)
  参考文献：
  名称：

  Arylazoimidazoleplatinum(II) complexes and their dioxolene derivatives: single crystal X-ray structure of (catecholato){1-ethyl-2-(p-tolylazo)-imidazole}platinum(II)

  摘要：

  The reaction of 1-ethyl-2-(arylazo)imidazoles (RaaiEt, 1) [R=H (1a), p-Me (1b), p-Cl (1c)] with K2PtCl4 in boiling acetonitrile-water (1:1) produces red-brown Pt(RaaiEt)Cl-2 (2) complexes. Addition of dioxolene in the presence of Et3N to chloroform-methanol solution of Pt(RaaiEt)Cl-2 has yielded green-coloured mixed-ligand complexes [Pt(RaaiEt)(O,O)] [O,O = catecholate (cat) (3), 4-tert-butylcatecholate (tbcat) (4), 3,5-di-tert-butylcatecholate (dtbcat) (5), tetrachlorocatecholate (tccat) (6)]. The structure of [Pt(p-MeaaiEt)(cat)].1/2H(2)O (3b) was confirmed by X-ray diffraction. Electronic spectra exhibit ligand-to-ligand charge transfer transition (LLCT) in the VIS-NIR region; the position and symmetry of the band depend on the substituent type on the dioxolene and arylazoimidazole frames. This is qualitatively assigned as a HOMO(cat)-->LUMO(RaaiEt) transition. Cyclic voltammograms of the complexes show four successive redox responses: two couples at positive to saturated calomel electrode (SCE) correspond to catechol to semiquinone and semiquinone to quinone oxidations, and two couples at negative to SCE correspond to the azo reductions. The difference in the potential E-1/2 of the first oxidation and reduction process changes linearly with the LLCT transition. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(00)00311-x

文献信息

• Syntheses and characterization of η5-cyclopentadienyl and η5-indenyl ruthenium(II) complexes of arylazoimidazoles: The molecular structure of the complex [(η5-C5H5)Ru(PPh3)(C6H5–N N–C3H3N2)]+
  作者：Padavattan Govindaswamy、Chittaranjan Sinha、Mohan Rao Kollipara

  DOI：10.1016/j.jorganchem.2005.04.042

  日期：2005.7

  R′ = CH3 (3), R = H, R′ = C2H5 (4), R = CH3, R′ = H (5), R, R′ = CH3 (6), R = CH3, R′ = C2H5 (7)}. The complex [(η5-C9H7)Ru(PPh3)2(CH3CN)]+ (8) undergoes reactions with a series of N,N-donor azo ligands in methanol yielding complexes of the type [(η5-C9H7) Ru(PPh3)(RaaiR′)]+ where R, R′ = H (9), R = H, R′ = CH3 (10), R = CH3, R′ = H (11), R = CH3, R′ = C2H5 (12)}, respectively. These complexes were characterized

  络合物[（η 5 -C 5 H ^ 5）的Ru（PPH 3）2 CL]（1）具有若干arylazoimidazole（RaaiR'）配位体，即发生反应，2-（苯偶氮基）咪唑（班派-H），1-甲基-2-（苯基偶氮）咪唑（Phai-Me），1-乙基-2-（苯基偶氮）咪唑（Phai-Et），2-（甲苯基）咪唑（Tai-H），1-甲基-2-（甲苯基基）咪唑（大-ME）和1-乙基-2-（tolylazo）咪唑（泰-ET），得到的类型的配合物[（η 5 -C 5 H ^ 5）的Ru（PPH 3）（RaaiR'）] + 其中R，R'= H（2），R = H，R'= CH 3（3），R = H，R'= C 2 H在图5（4）中，R ＝ CH 3，R′＝ H（5），R，R′＝ CH 3（6），R ＝ CH 3，R′＝ C 2 H 5（7）}。络合物[（η 5 -C 9 ħ 7）的Ru（PPH 3）2（CH
• Ruthenium(II) complexes of α-diimines: synthesis, spectral characterisation, electrochemical properties and single-crystal X-ray structure of bis(2,2′-bipyridine){1-benzyl-2-(p-tollylazo)imidazole}ruthenium(II) perchlorate
  作者：Sanjib Pal、Tarun K. Misra、Chittaranjan Sinha、Alexander M.Z. Slawin、J.Derek Woollins

  DOI：10.1016/s0277-5387(00)00447-2

  日期：2000.9

  [Ru(bpy)2(RaaiR′)](ClO4)2·H2O (bpy=2,2′-bipyridine; RaaiR′=1-alkyl-2-(arylazo)imidazole) have been synthesized by a silver-assisted route [Ru(bpy)2Cl2+RaaiR′+AgNO3+NaClO4/Ru(bpy)2Cl2+[Ag(RaaiR′)2](ClO4)]. The structures of the complexes have been supported by the single-crystal X-ray diffraction study and the stereochemistry are assessed by 1H NMR spectral data. All the complexes show two metal-to-ligand charge

  摘要混合配体三螯合物[Ru（bpy）2（RaaiR'）]（ClO4）2·H2O（bpy = 2,2'-联吡啶; RaaiR'= 1-烷基-2-（芳基偶氮）咪唑）具有通过银辅助路线[Ru（bpy）2Cl2 + RaaiR'+ AgNO3 + NaClO4 / Ru（bpy）2Cl2 + [Ag（RaaiR'）2]（ClO4）]合成。配合物的结构已得到单晶X射线衍射研究的支持，并通过1 H NMR光谱数据评估了立体化学。所有的络合物在约200nm的可见光区域均显示出两个金属至配体的电荷转移（MLCT）跃迁。此处还介绍了400和500 nm及其发射光谱。循环伏安研究显示，乙腈溶液中RuIII / II的电势较高（1.4 V vs. SCE），并且在SCE呈负值时连续出现三个配体还原。第一金属和后续配体氧化还原电势的差异与MLCT谱带的νCT线性相关。
• <i>trans</i>-Dichloro-bis-(arylazoimidazole)palladium(II): Synthesis, Structure, Photoisomerization, and DFT Calculation
  作者：P. Pratihar、T. K. Mondal、A. K. Patra、C. Sinha

  DOI：10.1021/ic8012365

  日期：2009.4.6

  of the complexes shows E-to-Z isomerization of the coordinated azoimidazole unit. The reverse transformation, Z-to-E, is very slow with visible light irradiation. Quantum yields (ϕE→Z) of E-to-Z isomerization are calculated, and ϕ is lower than that of the free ligand but comparable with those of Cd(II) and Hg(II) complexes of the same ligand. The Z-to-E isomerization is a thermally induced process

  分离出PdCl 2与1-烷基-2-（芳基偶氮）咪唑（RaaiR'）或1-烷基-2-（萘基-α/β-偶氮）咪唑（α/β-NaiR'）在乙醇中回流的反应组合物的Pd（RaaiR'）的复合物2氯2（5，6）和Pd（α/β-奈尔'）2氯2（7，8）。分子之一Pd（α-NaiBz）2 Cl 2（7c）的X射线结构测定已报告了反式-PdCl 2构型，并且α-NaiBz充当单齿N（咪唑）供体配体。光谱（IR，UV-vis，11 H NMR数据支持该结构。UV光照射（光源：PERKIN-Elmer公司LS 55荧光分光光度计，氙放电灯，λ= 360-396纳米）中的复合物显示了一个的MeCN溶液Ë -到- Ž协调azoimidazole单元的异构化。Z- to- E的反向转换在可见光照射下非常慢。计算出E- to- Z异构化的量子产率（ϕ E → Z），ϕ低于游离配体的量子产率，但与相同配体的Cd（II）
• Synthesis, spectral studies, crystal structure and redox properties of homoleptic tris-chelated ruthenium(II)-arylazoimidazoles
  作者：Sk. Jasimuddin、P. Byabartta、G. Mostafa、T.-H. Lu、C. Sinha

  DOI：10.1016/j.poly.2003.10.018

  日期：2004.3

  UV–Vis spectra of the complexes show an intense peak in the visible region (510–570 nm) and it has been assigned to a MLCT transition. Cyclic voltammetry of the complexes shows one metal oxidation Ru(II)/Ru(III) at 1.2–1.5 V and three successive ligand reduction couples negative to SCE as the reference electrode.

  Tris螯合的[Ru（o / p -RaaiR '）3 ] Cl 2（其中RaaiR ' = 1-烷基-（2-芳基偶氮）咪唑，R = H（5），p -Me（6）p -OMe（7）o- OMe（8），R '＝ Me（a），Et（b），CH 2 Ph（c））是通过微波技术制备的。配合物的特征在于IR，UV-Vis和1 H NMR光谱数据。在一种情况下[Ru（o-OMeaaiCH 2 Ph）3 ] Cl 2。配合物的UV-Vis光谱在可见光区域（510-570 nm）出现一个强烈的峰，并且已被指定为MLCT跃迁。配合物的循环伏安法显示在1.2–1.5 V时有一种金属氧化Ru（II）/ Ru（III），并且三个连续的配体还原对SCE负电偶作为参比电极。
• Mono- and binuclear cobalt(II)-azido complexes of arylazoimidazole: synthesis, spectral characterization, electrochemistry and crystal structure
  作者：Umasankar Ray、Brojogopal Chand、Golam Mostafa、Jack Cheng、Tian-Huey Lu、Chittaranjan Sinha

  DOI：10.1016/s0277-5387(03)00347-4

  日期：2003.8

  whereas the binuclear azide bridged complex (5b) has the distorted square pyramidal geometry around the cobalt(II) centre. Redox properties of the complexes are examined by cyclic voltammetry and show a high potential Co(III)/Co(II) couple along with ligand reductions. EHMO calculation and comparison between the two types of complexes explain the spectral and redox properties of the complexes.

  一旦设置了适当的反应条件下1-烷基-2-（芳基偶氮）咪唑（RaaiR'，其中R = H（一）中，Me（b）; R'=我（1 / 3 / 5），等。（2 / 4 / 6）可以用Co（OAC）反应2 ·4H 2 O和的NaN 3在甲醇溶液，得到两类叠氮基复合物：单核二-螯合[CO（RaaiR'）2（N 3）2 ]（3，4）和双核μ-（1,1）叠氮基桥接单螯合[Co（RaaiR'）（μ-（1）N 3）（μ-（1,1）N 3 ] 2（5，6）的复合物。它们具有紫外-可见，红外光谱，室温磁场的特征，并且已通过[Co（MeaaiMe）2（N 3）2 ]（3b）和[Co （μ-1 ）N 3 }（MeaaiMe）] 2（5b）。单核络合物（3b）扭曲为八面体，而双核叠氮化物桥联络合物（5b））在钴（II）中心周围具有扭曲的方形棱锥几何形状。通过循环伏安法检查复合物的氧化还原性质，并显示高电位的Co（III）/