1-ethyl-2-(4-chloro-phenylazo)imidazole | 198347-72-7

• 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-ethyl-2-(4-chloro-phenylazo)imidazole
• 英文别名: 1-ethyl-2-(p-chlorophenylazo)imidazole；1-ethyl-2-(p-Cl-C6H4-NN)imidazole；ClaaiEt；(4-Chlorophenyl)-(1-ethylimidazol-2-yl)diazene
• CAS: 198347-72-7
• 化学式: C₁₁H₁₁ClN₄
• 分子量: 234.688
• InChiKey: SIQLZJOZAZWSNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 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-(4-chloro-phenylazo)imidazole 在 (C₂H₅)3N 作用下， 以 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 生成 [Pt(C2H5C3H2N2N2C6H4Cl)(tetrachlorocatecholato)]
  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

• 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 + Na / Ru（bpy）2Cl2 + [Ag（RaaiR'）2]（ ）]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。
• Synthesis and multinuclear NMR investigation on gold(III)-triphenylphosphine-pentafluorophenyl-arylazoimidazole
  作者：P. Byabartta

  DOI：10.1134/s1070328409040046

  日期：2009.4

  Reaction of [Au(C6F5)(PPh3)(OSO2CF3)2] with RaaiR′ in dichloromethane medium followed ligand addition leads to [Au(PPh3)(C6F5)(RaaiR′)](OSO2CF3)2 where RaaiR′ = p-R-C6H4-N=N-C3H2-NN-1-R′ (I–III), abbreviated as N, N′-chelator, where N(imidazole) and N(azo) represent N and N′, respectively; R = H (a), Me (b), Cl (c) and R′ = Me (I), CH2CH3 (II), CH2Ph (III), PPh3 is triphenylphosphine, OSO2CF3 is the

  [Au（C 6 F 5）（PPh 3）（OSO 2 CF 3）2 ]与RaaiR'在二氯甲烷介质中的反应，然后进行配体添加，生成[Au（PPh 3）（C 6 F 5）（RaaiR'）] （OSO 2 CF 3）2，其中RaaiR'= p -RC 6 H 4 -N = NC 3 H 2 -NN-1-R'（I–III），缩写为N，N'-螯合剂，其中N（咪唑）和N（偶氮）分别代表N和N'；R = H（a），Me（b），Cl（c）和R'= Me（I），CH 2 CH 3（II），CH2 Ph（III），PPh 3是三苯基膦，OSO 2 CF 3是三氟甲磺酸根阴离子。在ESI质谱图中观察到相应分子的最大分子峰。配合物的红外光谱显示-C = N-和-N = N-由于三苯基膦和三苯基膦的存在而在〜1590和1370 cm -1附近以及在〜1100、755、695、545和505 cm -1附近拉伸。五氟苯环。的1个1
• AU-BPY-RAAIR: Gold(III)-2,2´-Bipyrimidine-ArylAzoImidazole Complexes: Synthesis and Spectral Cherecterisation
  作者：Prithwiraj Byabartta

  DOI：10.1016/j.molstruc.2023.136605

  日期：2024.1

  whereas direct substitution gives high yield. [RaaiR/ = p-R-C6H4-N=N-C3H2-NN-1-R/, (1-3), abbreviated as N,N/-chelator, where N(imidazole) and N(azo) represent N and N/, respectively; R = H (a), Me (b), Cl (c) and R/ = Me (1), CH2CH3 (2), CH2Ph (3), OSO2CF3 is the triflate anion, bpy is 2,2´-bipyridine]. The 1H NMR spectral measurements suggest methylene, –CH2–, in RaaiEt gives a complex AB type multiplet

  [Au(bpy)Cl 2 ]PF 6与AgOTf反应，然后添加配体，导致[Au(bpy)(RaaiR / )] 产率低，而直接取代则产率高。[RaaiR /  =  p -RC 6 H 4 -N=NC 3 H 2 -NN-1-R / , ( 1-3 )，缩写为N,N / -螯合剂，其中N(咪唑)和N(偶氮)分别代表 N 和 N /；R = H ( a )、Me ( b )、Cl ( c ) 且 R /  = Me ( 1 )、CH 2 CH 3( 2 )，CH 2 Ph ( 3 )，OSO 2 CF 3是三氟甲磺酸根阴离子，bpy 是2,2´-联吡啶]。1 H NMR 光谱测量表明，RaaiEt 中的亚甲基-CH 2 - 给出了复杂的AB 型多重峰，而RaaiCH 2 Ph 中则显示了AB 型四重峰。13 C NMR谱反映了分子骨架。在本配合物的1 H- 1 H COSY 谱和本配合物的1
• Palladium(II)-dppe-arylazoimidazole complexes: Synthesis, and spectroscopic characterization
  作者：Prithwiraj Byabartta

  DOI：10.1134/s0036023610070107

  日期：2010.7

  Reaction of [Pd(dppe)Cl-2/Br-2] with AgOTf in a dichloromethane medium followed by ligand addition led to [Pd(dppe)(OSO2CF3)(2)] and then [Pd(dppe)(RaaiR)](OSO2CF3)(2) [RaaiR' = p-R-C6H4-N=N-C3H2-NN-1-R', (1-3), abbreviated as a N,N'-chelator, where N(imidazole) and N(azo) are represented by N and N', respectively; R = H (a), Me (b), Cl (c) and R' = Me (1), CH2CH3 (2), CH2Ph (3), OSO2CF3 is the triflate anion, dppe = 1,2-bis-(diphenylphosphinoethane)]. P-31 "H-1" NMR confirmed that due to the two phosphorus atom interaction in the azoimine symmetrical environment one sharp peak was formed. The H-1 NMR spectral measurements suggest that azo-imine link with lot of phenyl protons in the aromatic region. C-13 (H-1) NMR spectrum, H-1, H-1 COSY and H-1, C-13 HMQC spectrum assign the solution structure and stereo-retentive conformation in each complex.
• Misra; Das; Sinha, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1998, vol. 37, # 8, p. 739 - 742
  作者：Misra、Das、Sinha

  DOI：——

  日期：——