2-(4-chlorophenylazo)aniline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2-(4-chlorophenylazo)aniline
• 英文别名: 2-(p-chlorophenylazo)aniline
• 化学式: C₁₂H₁₀ClN₃
• 分子量: 231.685
• InChiKey: BXUBCSWZPJOBRM-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.74
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenylazo)aniline 以 甲醇 、 二甲基亚砜 为溶剂， 生成 [(2-(p-chlorophenylazo)aniline-H)Pt(acetylacetone-H)]
  参考文献：
  名称：

  铂 (II) 和钯 (II) 重氮酮亚胺络合物的合成、结构和反应性：铂络合物的细胞毒性

  摘要：

  2-(芳基偶氮)苯胺的反应Ar-N=N-C6H4NH2[HLnNH2; Ar = C6H5 (HL1)、p-CH3C6H4 (HL2)、p-ClC6H4 (HL3)] 与 dmso 中的 K2PtCl4 提供新的 PtII 偶氮亚胺配合物 [(HLnNH)Pt(dmso)Cl]，其中氯化物和 dmso 配体相互顺式. 相反，在 dmso 中用 HLnNH2 处理 Na2PdCl4 得到氯桥连钯二聚体 [{(HLnNH)PdCl}2] 作为主要产物以及 [(HLnNH)2Pd] 作为次要产物。此外，HLnNHCH2Ph 与 K2PtCl4 在 dmso 中的反应也产生 [(HLnNH)Pt(dmso)Cl]，而 Na2PdCl4 提供正钯化配合物 [(LnNHCH2Ph)PdCl]。这意味着 N-C(CH2Ph) 键被 K2PtCl4 选择性地裂解。[(HLnNH)Pt(dmso)Cl] 与乙酰丙酮

  DOI：

  10.1002/ejic.200700350

文献信息

• Regiospecific <i>ortho</i> ‐Aromatic Hydroxylation via Cyclonickelation Using Hydrogen Peroxide and Other Oxygen Donors: Synthesis of Metalloazosalophens
  作者：Poulami Pattanayak、Jahar Lal Pratihar、Debprasad Patra、Andrew Burrows、Mary Mohan、Surajit Chattopadhyay

  DOI：10.1002/ejic.200700149

  日期：2007.9

  The dianionic (L sal ) 2- ligands bind Ni II in tetradentate (C,N,N,O) fashion in distorted square-planar geometry. Reaction of (L sal )Ni with meta-chloroperbenzoic acid, tert-butyl hydroperoxide, or hydrogen peroxide furnished the metalloazosalophens, (OL sal )Ni, as a result of oxygen insertion into the Ni-C bond. The X-ray structures of (L 1 sal )Ni and (OL 1 sal )Ni were determined as representatives

  新的配体 N-[2-(芳基偶氮)苯基]水杨亚胺，H 2 L sal [其中 H 代表络合时的可解离质子，H 2 L sal 的芳基是 H 2 L 1 sal 的苯基，H 的对甲基苯基通过2-(芳基偶氮)苯胺H 2 L与水杨醛的反应制备2 L 2 sal 和用于H 2 L 3 sal ]的对氯苯基。H 2 L sal 配体在用 Ni(CH 3 -COO) 2 .4H 2 O 处理后提供稳定的原金属化配合物 (L sal )Ni。双阴离子 (L sal ) 2- 配体以四齿 (C,N ,N,O) 以扭曲的方形平面几何形式呈现。(L sal )Ni 与间氯过苯甲酸、叔丁基过氧化氢或过氧化氢的反应提供了金属偶氮唑盐 (OL sal )Ni，这是氧插入 Ni-C 键的结果。(L 1 sal )Ni 和 (OL 1 sal )Ni 的 X 射线结构被确定为明确表征的代表。用稀HClO 4 处理(OL 1
• Reactions of 2-(arylazo)aniline with ruthenium substrates: Isolation, characterizations and reactivities of delocalized diazoketiminato and orthometallated Ru(II) chelates
  作者：Jahar Lal Pratihar、Shantanu Bhaduri、Poulami Pattanayak、Debprasad Patra、Surajit Chattopadhyay

  DOI：10.1016/j.jorganchem.2009.06.038

  日期：2009.10

  Reactions of 2-(arylazo)aniline, HL-NH2 [H represents the dissociable protons upon complexation and HL-NH2 is p-RC6H4N=NC6H4-NH2; R = H for HL1-NH2; CH3 for HL2-NH2 and Cl for HL3-NH2] with Ru(H) (CO)(PPh3)(3)Cl and Ru(CO)(3)(PPh3)(2) afforded products of compositions [(HL-NH)Ru(CO)Cl(PPh3)(2)] and [(L-NH)Ru(PPh3)2(CO)], respectively. All the complexes were characterized unequivocally. The X-ray structures of the complexes 4c and 5c have been determined. The cyclic volatammograms exhibited one reversible oxidative response in the range of 0.56-0.16 V versus SCE for [(L-NH)Ru(PPh3)(2)(CO)] and a quasi reversible oxidative response within 0.56-0.70 V versus SCE for [(HL-NH)Ru(CO)Cl(PPh3)(2)]. The conversion of ketones to corresponding alcohols has been studied in presence of newly synthesized ruthenium complexes. (C) 2009 Elsevier B.V. All rights reserved.
• Syntheses, characterization, structure and redox properties of new Rh(III) cyclometallates incorporating azoimine ligands
  作者：Jahar lal Pratihar、Debprasad Patra、Surajit Chattopadhyay

  DOI：10.1016/j.jorganchem.2005.07.076

  日期：2005.11

  The reaction of 2-(arylazo) aniline, 1 (HL-NH2) [where HL-NH2 is 2-(ArN=N)C6H4-NH2; Ar = C6H5 (for HL1-NH2), p-MeC6H4(for HL2-NH2) and p-ClC6H4(for HL3-NH2). H of HL stands for dissociable proton of Ar due to orthometallation], with Rh(PPh3)(3)Cl (Wilkinson's catalyst) furnished the cyclometallated azoimine complexes of composition (L-NH)Rh(PPh3)(2)Cl (2). All the complexes were characterized by spectroscopic technique and confirmed by X-ray structure determination of (L-3-NH)-Rh(PPh3)(2)Cl as a representative one. The azoimine chelate ring size of 2 is five membered where the phenyl ring adjacent to the chelate ring is distorted with four longer and two shorter bonds. This structural feature has been attributed to the delocalization of negative charge of the anionic ligands that formed in situ from the precursor (HL-NH2) due to dissociation of an amino proton. The (L-NH)Rh(PPh3)(2)Cl complexes display an one electron oxidative response in the range of 0.331 to 0.436 V vs. SCE. (c) 2005 Elsevier B.V. All rights reserved.
• Syntheses and properties of new metal–carbon bonded heteroleptic complexes of ruthenium(II) containing terpyridine coligand
  作者：Jahar Lal Pratihar、Poulami Pattanayak、Jui-Hsien Huang、Surajit Chattopadhyay

  DOI：10.1016/j.ica.2009.09.024

  日期：2009.12

  Reactions of 2-(arylazo) aniline, HL [H represents the dissociable protons upon orthometallation and HL is p-RC6H4N = NC6H4-NH2; R = H for HL1; CH3 for HL2 and Cl for HL3] with Ru(R-1-tpy)Cl-3 (where R-1-tpy is 4'-(R-1)-2,2',6 '',2 ''-terpyridine and R-1 = H or 4-N, N-dimethylaminophenyl or 4-methylphenyl) afford a group of complexes of type [Ru(L)(R-1-tpy)]center dot ClO4 each of which contains C, N, N coordinated L-as a tridentate ligand along with a terpyridine. Structure of one such complex has been determined by X-ray crystallography. All the Ru(II) complexes are diamagnetic, display characteristic H-1 NMR signals and intense d pi(Ru-II) -> pi*(tpy) MLCT transitions in the visible region. Cyclic voltammetric studies on [Ru(L)(R-1-tpy)]center dot ClO4 complexes show Ru(II)-Ru(III) oxidation within 0.63-0.67 V versus SCE. (C) 2009 Elsevier B. V. All rights reserved.
• Reactions of 2-(arylazo)aniline with iridium trichloride: Synthesis, characterization and structure of new cyclometallated complexes of iridium(III)
  作者：Jahar Lal Pratihar、Poulami Pattanayak、Debprasad Patra、Rajendra Rathore、Surajit Chattopadhyay

  DOI：10.1016/j.ica.2010.12.025

  日期：2011.2

  Reactions of 2-(arylazo)aniline, HL (H represents the dissociable protons upon orthometallation and HL is p-RC6H4N=NC6H4-NH2; R=H for HL1; CH3 for HL2 and Cl for HL3) with IrCl3 in methanol afforded ortho-metallated complexes of composition (L)(HL)IrCl2 (2) and (L)(MeOH)IrCl2 (3), respectively. Complex (L)(MeOH)IrCl2 (3) converted into (L)(CH3CN)IrCl2 (4) upon refluxing in acetonitrile. The X-ray structure of the complexes (L-1)(HL1)IrCl2 (2a) and (L-3)(CH3CN)IrCl2 (4c) have been determined and characterized unequivocally. The anionic L binds the metal in tridentate (C, N, N) manner for all the complexes. (C) 2011 Elsevier B.V. All rights reserved.