3-(p-tolyl)-1,5-diphenylformazan | 1622-12-4

• 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: 3-(p-tolyl)-1,5-diphenylformazan
• 英文别名: 1,5-diphenyl-3-p-tolylformazan；1,5-Diphenyl-3-(p-tolyl)formazan；N'-anilino-4-methyl-N-phenyliminobenzenecarboximidamide
• CAS: 1622-12-4
• 化学式: C₂₀H₁₈N₄
• 分子量: 314.39
• InChiKey: FEYZMOAOMKSFOX-UHFFFAOYSA-N

物化性质

• 熔点：
  154 °C
• 沸点：
  454.1±38.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  3-(p-tolyl)-1,5-diphenylformazan 在 thallium(III) acetate 作用下， 以 水 、 溶剂黄146 为溶剂， 以95%的产率得到Acetate2,3-diphenyl-5-p-tolyl-3H-tetrazol-2-ium;
  参考文献：
  名称：

  Balakrishnan, R.; Srinivasan, Vangular S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 8, p. 771 - 775

  摘要：

  DOI：
• 作为产物：
  描述：

  苯肼,盐酸盐 在 盐酸 、 sodium acetate 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 16.0h， 生成 3-(p-tolyl)-1,5-diphenylformazan
  参考文献：
  名称：

  Synthesis and Electrochemical Properties of 2-(4-R1-Phenyl)-6-(4-R2-phenyl)-4-phenyl-3,4-dihydro1,2,4,5-tetrazin-1(2H)-yls

  摘要：

  A new methodology for creating electroactive components for organic batteries, based on the construction of a molecular platform including stable 3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yl radicals was described. A series of 2-(4-R-1-phenyl)-6-(4-R-2-phenyl)-4-phenyl-3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yls with substituents of various nature was obtained. It was shown that the substituents R-1 in the aromatic ring at position 2 of the tetrazinyl fragment influence the value of the oxidation potential in the radical, but do not influence the value of the reduction potentials, while the substituent R-2 of the aromatic ring at position 6 influence the values of the reduction potentials and practically do not influence oxidation potential values. Based on the obtained electrochemical data, a correlation structure-potential value was revealed for the cathodic and anodic process, with the help of which triarylsubstituted 3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yl radicals with high values of the electrochemical gap were obtained.

  DOI：

  10.1134/s1070363220030044

文献信息

• Reversible Ligand-Centered Reduction in Low-Coordinate Iron Formazanate Complexes
  作者：Daniël L. J. Broere、Brandon Q. Mercado、James T. Lukens、Avery C. Vilbert、Gourab Banerjee、Hannah M. C. Lant、Shin Hee Lee、Eckhard Bill、Stephen Sproules、Kyle M. Lancaster、Patrick L. Holland

  DOI：10.1002/chem.201801298

  日期：2018.7.2

  Coordination of redox‐active ligands to metals is a compelling strategy for making reduced complexes more accessible. In this work, we explore the use of redox‐active formazanate ligands in low‐coordinate iron chemistry. Reduction of an iron(II) precursor occurs at milder potentials than analogous non‐redox‐active β‐diketiminate complexes, and the reduced three‐coordinate formazanate‐iron compound

  氧化还原活性配体与金属的配位是使还原复合物更容易获得的一个引人注目的策略。在这项工作中，我们探索了氧化还原活性甲氮酸盐配体在低配位铁化学中的用途。与类似的非氧化还原活性 β-二酮亚胺复合物相比，铁（II）前体的还原发生在更温和的电位下，并且对还原的三配位甲氮酸铁化合物进行了详细表征。结构、光谱和计算分析表明，甲臜酸配体经历可逆的配体中心还原，在还原物质中形成甲臜酸自由基双阴离子。还原的低配位甲氮酸铁络合物的负还原电位较小，导致独特的反应性，形成新的 N-I 键，而 β-二酮亚胺类似物则没有这种键。因此，支持配体上电子的存储改变了氧化还原电位并增强了某些反应性。
• Highly Selective Single‐Component Formazanate Ferrate(II) Catalysts for the Conversion of CO ₂ into Cyclic Carbonates
  作者：Aeilke J. Kamphuis、Francesca Milocco、Luuk Koiter、Paolo P. Pescarmona、Edwin Otten

  DOI：10.1002/cssc.201900740

  日期：2019.8.8

  anionic mono(formazanate) iron(II) complexes bearing labile halide ligands, which possess both Lewis acidic and nucleophilic functionalities, have been developed as novel single‐component homogeneous catalysts for the reaction of CO2 with epoxides to produce cyclic carbonates. The influence of the halide ligand and the electronic properties of the formazanate ligand backbone on the catalytic activity

  从可持续化学的角度来看，基于富稀土金属的新型活性和选择性单组分催化剂家族的发展是令人感兴趣的。在这种情况下，具有路易斯酸和亲核官能团的带有不稳定卤化物配体的阴离子单（甲酸）铁（II）络合物已被开发为用于CO 2反应的新型单组分均相催化剂。与环氧化物生产环状碳酸酯。卤化物配体和甲酸酯配体主链的电子性质对催化活性的影响是通过使用铁（II）配合物（有或没有其他亲核试剂）来研究的。在不需要助催化剂的情况下，从各种末端和内部环氧化物形成环状碳酸酯产品的选择性非常高。
• Microwave mediated solvent free synthesis of formazans catalyzed by simple ionic liquids derived from dialkylammonium salts
  作者：Pranab Jyoti Das、Jesmin Begum

  DOI：10.1039/c5ra06363a

  日期：——

  Microwave assisted solvent free one pot synthesis of formazans, catalysed by ionic liquid is reported for the first time.

  首次报道了离子液体催化的微波辅助无溶剂一锅法合成甲醛胺。
• Formazans as β-diketiminate analogues. Structural characterization of boratatetrazines and their reduction to borataverdazyl radical anions
  作者：Joe B. Gilroy、Michael J. Ferguson、Robert McDonald、Brian O. Patrick、Robin G. Hicks

  DOI：10.1039/b609365e

  日期：——

  Formazans react with boron triacetate to produce boratatetrazines, which can be reduced to yield borataverdazyl radical anions—the first boron containing verdazyl radicals.

  福尔马赞与三乙酸硼反应生成硼酚四嗪，这些化合物可以被还原生成含硼的维尔达氮自由基阴离子——第一种含硼的维尔达氮自由基。
• Three-Coordinate Zinc Methyl Complexes with Sterically Demanding Formazanate Ligands
  作者：Folkert de Vries、Raquel Travieso-Puente、Peter Roewen、Edwin Otten

  DOI：10.1021/acs.organomet.0c00720

  日期：2021.1.11

  methyl complexes were synthesized, and the influence of the ligand on the structure as well as redox and optical properties of these complexes was investigated. The heteroleptic mono(formazanate)zinc methyl complexes were found to show ligand redistribution in solution, reminiscent of the Schlenk equilibrium, to generate an equilibrium mixture containing the corresponding homoleptic complexes as well

  合成了一系列杂配的三配位单（甲酸）锌锌甲基配合物，研究了配体对这些配合物的结构，氧化还原和光学性质的影响。发现杂合单（甲酸酯基）锌甲基复合物在溶液中显示出配体重新分布，使人联想到Schlenk平衡，从而产生了也包含相应的均纯复合物的平衡混合物。通过NMR光谱法监测苯-d 6中的平衡方法允许确定前向和后向速率常数。在锌中心周围的空间环境与（甲酸酯基）锌甲基化合物的平衡浓度之间发现相关性，而达到平衡的动力学也取决于电子性质。