2-((4-氯苯基)偶氮)吡啶 | 14458-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-((4-氯苯基)偶氮)吡啶
• 英文名称: 2-(4-chlorophenylazo)pyridine
• 英文别名: (4-Chlorophenyl)-pyridin-2-yldiazene
• CAS: 14458-12-9
• 化学式: C₁₁H₈ClN₃
• 分子量: 217.658
• InChiKey: SWWILIMFRGAWGS-UHFFFAOYSA-N

物化性质

• 熔点：
  123-124 °C
• 沸点：
  359.7±22.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-((4-氯苯基)偶氮)吡啶 在 triethylamine 作用下， 以 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 生成 catecholato-(2-(p-chlorophenylazo)pyridine)platinum(II)
  参考文献：
  名称：

  Synthesis, spectral characterization and electrochemical studies of mixed-ligand complexes of platinum(II) with 2-(arylazo)pyridines and catechols. Single-crystal X-ray structure of dichloro{2-(phenylazo) pyridine}platinum(II)

  摘要：

  The reaction of 2-(arylazo)pyridines, RH4C6N=NC5H4N (aap, 1 where R=H (pap), p-Me (p-tap), p-Cl (p-Clpap)) with K2PtCl4 in 1:2 boiling acetonitrile-water affords orange-red complexes of the type Pt(aap)Cl-2 (2). The IR spectrum shows two v(Pt-Cl) stretches suggesting cis-PtCl2 configuration. The structural confirmation was carried out by an X-ray diffraction study of Pt(pap)Cl-2 (2a). The addition of catechols to a chloroform-methanol solution of Pl(aap)Cl-2 in the presence of Et3N yielded green colored mixed-ligand complexes of the formula Pt(aap)(O,O) (O,O = catecholate (cat) (3), 4-tert-butylcatecholate (tbcat), (4), 3,5-di-tert-butylcatecholate (dtbcat) (5) and tetrachlorocatecholate (tccat) (6)). The complexes were characterized by elemental analyses, IR, W-Vis-NIR and H-1 NMR spectral data. Electronic spectra exhibit a ligand-ligand charge transfer (LLCT) transition at NIR region; the position and symmetry of the band depend on the type of substituent on the catechol frame. This is qualitatively assigned as 3b(1)(cat)-->pi*(aap) transition. Cyclic voltammogram of the complexes show four successive redox responses: two couples positive to SCE are referred to as oxidation of catechol to semiquinone and semiquinone to quinone, respectively and two couples negative to SCE correspond to azo reductions. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0277-5387(00)00530-1

文献信息

• Ruthenium terpyridine complexes incorporating azo-imine based ancillary ligands. Synthesis, crystal structure, spectroelectrochemical properties and solution reactivities †
  作者：Biplab Mondal、Mrinalini G. Walawalkar、Goutam Kumar Lahiri

  DOI：10.1039/b005789o

  日期：——

  Ruthenium terpyridine complexes of the type [RuII(trpy)(L)(X)][ClO4]n1–15 [trpy = 2,2′∶6,2′′-terpyridine; L = NC5H4NNC6H4(R), R = H, m-Me, m-Cl, p-Me or p-Cl; X = Cl−, n = 1 (1–5); H2O, n = 2 (6–10) or OH−, n = 1 (11–15)] have been synthesized. The single crystal structures of 1 and 6 were determined. Complex 4 develops in two possible isomeric forms whereas all other complexes stabilise preferentially

  [Ru II（trpy）（L）（X）] [ClO 4 ] n 1–15 [trpy = 2,2'∶6,2''-叔吡啶；L = NC 5 H 4 N NC 6 H 4（R），R = H，m -Me，m -Cl，p -Me或p -Cl；X =氯- ，Ñ  = 1（1-5）;高氧2，Ñ  = 2（6-10）或OH - ，Ñ  = 1（11-15）]已被合成。确定了1和6的单晶结构。配合物4以两种可能的异构形式发展，而所有其他配合物优先以一种异构形式稳定。该复合物在500 nm附近表现出很强的MLCT谱带，并且配体紫外线区域中的基于过渡的过渡。1–5在600 nm附近的77 K处显示中等强度的发射。这氯代（1–5）和羟基（11–15）配合物显示钌（III）–钌（II）对以及3至4个连续的单电子配体基于减少量。水复合物（6–10）表现出可逆的2e − / 2H +单步氧化作用在[Ru II（trpy）（L）（H
• Effects of Ancillary Ligands on Redox and Chemical Properties of Ruthenium Coordinated Azoaromatic Pincer
  作者：Santi Prasad Rath、Debabrata Sengupta、Pradip Ghosh、Rameswar Bhattacharjee、Mou Chakraborty、Subhas Samanta、Ayan Datta、Sreebrata Goswami

  DOI：10.1021/acs.inorgchem.8b01558

  日期：2018.10.1

  the catalytic efficiency is primarily controlled by the electronic effect of the coligand. Accordingly, the complex [2]+ (containing a strong π-acceptor coligand, pcp) brings about oxidation efficiently, producing 86% of benzaldehyde. In comparison, however, the complexes 4 and 5 (containing electron donating coligand) furnished only 15–20% of benzaldehyde under identical reaction conditions. Investigations

  在这项工作中，研究了电子不同的辅助配体对通式为[RuLQCl] 0 / +的杂合配合物中Ru II L部分（L = 2,6-双（苯基偶氮）吡啶）的整体性质的影响。使用四种具有不同电子效应的不同辅助配体（Q）从前体复合物[RuL（CH 3 CN）Cl 2 ]（1）制备杂配化合物。Q ＝ pcp：2-（4-氯-苯基偶氮）吡啶（强π-受体），[ 2 ] +；bpy：2，2′-联吡啶（中度π-受体），[ 3 ] +；acac –：乙酰丙酮酸（强σ-供体），4; 和DTBCat 2–：3,5-儿茶酚酸二叔丁酯（强π-供体），5。络合物[ 2 ] +，[ 3 ] +，4和5被充分表征并在结构上被确定。这些配合物及其氧化还原伙伴的电子结构通过大量物理测量得以阐明：核磁共振，循环伏安法，电子顺磁共振，紫外可见近红外光谱和密度泛函理论。研究表明大肠菌素对RuL部分的偶氮键长度及其氧化还原行为具有显着影响。考
• Chemistry of Metal-Bound Anion Radicals. A Family of Mono- and Bis(azopyridine) Chelates of Bivalent Ruthenium
  作者：Maya Shivakumar、Kausikisankar Pramanik、Indranil Bhattacharyya、Animesh Chakravorty

  DOI：10.1021/ic000356b

  日期：2000.9.18

  and 6+PF6- are isolated, H+ being the oxidizing agent. The X-ray structures of 4+PF6-.CH2Cl2, 5+PF6-.H2O, and 6+PF6- have been determined. In the monoradical 4+ the azo N-N bond lengths in the two chelate rings are 1.284(6) and 1.336(6) A, showing that the radical electron is localized in the latter ring. The half-filled extended Hückel HOMO is indeed found to be so localized, and it has a large azo

  二氢化物[RuII（H）2（CO）（PPh3）3]，3与过量的偶氮-2,2'-联吡啶（abp）在沸腾的干燥苯中的反应提供了双自由基双螯合物[RuII（abp.- ）2（CO）（PPh3）]，4和氢化单螯合物单自由基[RuII（abp .-）（H）（CO）（PPh3）2]，5。3和2-（对氯苯基偶氮）之间的相似反应）吡啶（Clpap）没有生成双螯合物，但已分离出羟基单自由基[RuII（Clpap .-）（H）（CO）（PPh3）2] 6。在湿的二氯甲烷-乙腈介质中用NH 4 PF 6处理4-6时，分离出单电子氧化的盐4 + PF 6-，5 + PF 6-和6 + PF 6-，其中H +为氧化剂。已确定4 + PF6-.CH2Cl2、5 + PF6-.H2O和6 + PF6-的X射线结构。在单自由基4+中，两个螯合环中的偶氮NN键长为1.284（6）和1.336（6）A，说明自由基电子位于后一
• Size-selective Pt siderophores based on redox active azo-aromatic ligands
  作者：Debabrata Sengupta、Sreetosh Goswami、Rajdeep Banerjee、Matthew J. Guberman-Pfeffer、Abhijeet Patra、Anirban Dutta、Rajib Pramanick、Shobhana Narasimhan、Narayan Pradhan、Victor Batista、T. Venkatesan、Sreebrata Goswami

  DOI：10.1039/d0sc02683b

  日期：——

  π-acceptor azo aromatic ligands (L) that spontaneously ionize and chelate Pt atoms selectively from nanoparticles of size ≤6 nm. The reaction produces a monometallic diradical complex, PtII(L˙−)2, isolated as a pure crystalline compound. Density functional theory provides fundamental insights on the size dependent PtNP chemical reactivity. The reported findings reveal a generalized platform for designing

  我们展示了一种受自然铁载体启发的溶解铂纳米粒子的策略，该策略可以使其尺寸选择合成，毒理学评估以及这种贵金属的回收利用。从电子产品的制造到生物医学的诊断和治疗，PtNP的使用越来越多。减轻对潜在的人类毒性的关注以及从工业废料中回收贵金属的需求，推动了对生物友好型试剂的研究，以取代传统的苛刻蚀刻剂。在此，我们报道了一个氧化还原活性铁载体族。π受体偶氮芳族配体（L）从尺寸≤6 nm的纳米粒子中自发地离子化和螯合Pt原子。的反应产生单金属二基络合物，铂II（L - ）2分离为纯净结晶化合物。密度泛函理论提供了与尺寸相关的PtNP化学反应性的基本见识。报告的发现揭示了用于设计π受体配体以调节Pt或其他贵金属NP溶解大小阈值的通用平台。例如，我们的方法可用于生成基于Pt的治疗剂或回收在催化转化器或电子制造行业中形成的Pt纳米碎屑。
• A Convenient Synthesis and Structural Assessment of [Sn(CH₃)₂(L₂)](ClO₄)₂
  作者：D. Dey、T. S. Basu Baul、E. Rivarola

  DOI：10.1246/bcsj.66.1556

  日期：1993.5

  A general synthesis for a novel class of complexes of the type, [Sn(CH3)2(L2)](ClO4)2 (L = 2-(substituted arylazo) pyridine) is reported. The structure of the complexes have been investigated by 119tin Mössbauer spectroscopy and NMR coupling constant 2J (117/119 Sn–CH). Further, the extent of distortion of tin–methyl groups in octahedral complexes have been calculated from the quadrupole shift (Q.S.) values using Parish’s relationship.

  报告了[Sn(CH3)2(L2)](ClO4)2（L = 2-（取代的芳基偶氮）吡啶）类新型配合物的一般合成方法。通过 119tin 莫斯鲍尔光谱和核磁共振耦合常数 2J (117/119 Sn-CH)，研究了这些配合物的结构。此外，还利用帕里什关系从四极位移（Q.S.）值计算出八面体配合物中锡甲基的变形程度。