3-nitro-1,5-diphenylformazan | 4453-80-9

• 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-nitro-1,5-diphenylformazan
• 英文别名: 3-nitro-1,5-di-p-tolylformazan；1,5-diphenyl-3-nitroformazan；C-Nitro-formazyl；N.N'-Diphenyl-C-nitro-formazan；N'-anilino-1-nitro-N-oxido-N-oxo-N-phenyliminomethanimidamide
• CAS: 4453-80-9
• 化学式: C₁₃H₁₁N₅O₂
• 分子量: 269.263
• InChiKey: ZURUWJIOBITTCE-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  423.6±28.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  3-nitro-1,5-diphenylformazan 在 ammonium sulfide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 生成 二苯基硫代卡巴肼
  参考文献：
  名称：

  Synthesis and kinetics of electronically altered photochromic dithizonatophenylmercury(II) complexes

  摘要：

  A series of phenyl-substituted dithizones were synthesized, and preparation of the corresponding series of photochromic phenylmercury(II) complexes is for the first time reported. Adaption of previous methods enhanced synthesis convenience and product yields. A single crystal X-ray data collection of the ortho-S-methyl nitroformazan reaction intermediate was done. ADF computed molecular orbitals of the title compound show the HOMO and LUMO orbitals stretching along the entire ligand. The spontaneous back reaction kinetics of dithizonatophenylmercury(II) was studied at varied concentrations, temperatures and in different solvents. An exponential correlation was found between the rate of reverse isomerization and temperature, while increased solvent polarity and decreased molar mass facilitate higher return rates. The kinetic study of the series of twelve electronically altered complexes yielded a lowest rate of 0.0002 s(-1) the ortho-methyl derivative, while the highest rate of 0.0106 s(-1) was measured for the meta-methoxy derivative. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.11.009
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 3-nitro-1,5-diphenylformazan
  参考文献：
  名称：

  Bamberger; Schmidt,O., Chemische Berichte, 1901, vol. 34, p. 586,588

  摘要：

  DOI：

文献信息

• Convenient synthesis and antibacterial activity of novel 5-phenyldiazenyl-1,3,4-thiadiazole derivatives
  作者：Fatma M. Saleh、Mirna T. Helmy、Hamdi M. Hassaneen

  DOI：10.1080/10426507.2020.1858081

  日期：2021.5.4

  presence of triethylamine afforded the corresponding 1,3,4-thiadiazole derivatives 10, 11, 13, 14 and 22–29. Stirring of N,2-diaryldiazene-1-carbohydrazonoyl chlorides 1–3 with thioanilides 31A–E in acetonitrile at room temperature in the presence of triethylamine gave the corresponding 1,3,4-thiadiazol-2(3H)-ylidene derivatives 34–36. The structures of all new compounds 10, 11, 13, 14, 22–29 and 34–36

  摘要 的反应Ñ，2- diaryldiazene -1- carbohydrazonoyl氯化物1,2与2 - （（甲硫基）-carbonthioyl）腙7,12和18-21的无水乙醇在三乙胺，得到存在室温下相应的1,3- ，4-噻二唑衍生物10，11，13，14和22-29。在室温下，在三乙胺存在下，在乙腈中用硫代苯胺31A-E搅拌N，2-二芳基二氮杂-1-碳酰重氮酰氯1-3，得到相应的1,3,4-噻二唑-2（3 H）-亚烷基衍生物34 –36。所有新化合物的结构通过元素分析和光谱数据确定了10、11、13、14、22-29和34-36。研究了一些针对金黄色葡萄球菌和大肠杆菌的新合成化合物，最有效的化合物是3-苯基-5-（苯基二氮烯基）-2-（（1-（吡啶-2-基）亚乙基）hydr基）-2,3-二氢-1,3,4-噻二唑（13c），2-（（1-（吡啶-2-基）亚乙基）肼基）-3-（对甲苯基）-5-（对甲苯二重氮基）-2
• Effect of Extended π Conjugation on the Spectroscopic and Electrochemical Properties of Boron Difluoride Formazanate Complexes
  作者：Stephanie M. Barbon、Viktor N. Staroverov、Joe B. Gilroy

  DOI：10.1021/acs.joc.5b00620

  日期：2015.5.15

  19F NMR spectroscopy, cyclic voltammetry, infrared spectroscopy, UV–vis absorption and emission spectroscopy, and mass spectrometry. X-ray crystallography and electronic structure calculations were used to rationalize the trends observed, including direct comparison of 3-cyano-, 3-nitro-, and 3-phenyl-substituted BF2 formazanate complexes. In all cases, the wavelengths of maximum absorption and emission

  通过系统比较苯基和萘基取代的衍生物，研究了扩展π共轭对二氟化硼（BF 2）甲酸酯配合物的光谱和电化学性质的影响。所描述的每个BF 2络合物均具有1 H，13 C，11 B和19 F NMR光谱，循环伏安法，红外光谱，UV-vis吸收和发射光谱以及质谱的特征。使用X射线晶体学和电子结构计算来合理化观察到的趋势，包括直接比较3-氰基，3-硝基和3-苯基取代的BF 2甲maz络合物。在所有情况下，随着π共轭的系统扩展（通过用萘基取代苯基），最大吸收和发射的波长发生红移，荧光量子产率提高（最高10倍），甲maz络合物向其的电化学转化自由基负离子和二价阴离子的负电势较小（更易于还原）。
• Heteroligand o‐Semiquinonato Cobalt Complexes of 3‐Cyano and 3‐Nitroformazans
  作者：Natalia A. Protasenko、Maxim V. Arsenyev、Evgeny V. Baranov、Alyona A. Starikova、Artem S. Bogomyakov、Vladimir K. Cherkasov

  DOI：10.1002/ejic.202200152

  日期：2022.6.17

  The synthesis and detailed characterization of new heteroligand o-semiquinonate cobalt complexes of bidentate 3-cyano- and 3-nitroformazans are reported to establish the influence of electron-withdrawing groups at R3 position of formazanate ligand on magnetic and electrochemical behavior of the complexes.

  据报道，双齿 3-氰基和 3-硝基甲臜的新型异配体邻半醌钴配合物的合成和详细表征确定了甲酸盐配体 R 3位上的吸电子基团对配合物的磁性和电化学行为的影响。
• Cobalt(III) Bis-o-semiquinone Complexes with p-Tolyl-Substituted Formazan Ligands: Synthesis, Structure, and Magnetic Properties
  作者：N. A. Protasenko、E. V. Baranov、I. A. Yakushev、A. S. Bogomyakov、V. K. Cherkasov

  DOI：10.1134/s1070328422700129

  日期：2022.12

  and 2167095 (III)). According to the XRD results and magnetic and spectral measurement data, compounds I–III are complexes of low-spin cobalt(III) bound to two radical anion o-semiquinone ligands and one formazan anion. The magnetic behavior of the complexes in a temperature range of 2–300 K is characterized by intramolecular antiferromagnetic exchange interactions between the o-semiquinone ligands

  摘要 新杂配体钴 (III) 双 3,6-二叔丁基-邻苯并半醌与对甲苯基取代的甲臜配体 Co(3,6-SQ) 2 L n (L 1 H 为 1,5- diphenyl-3- p -tolylformazan ( I ), L 2 H 为 1,3,5-tri- p -tolylformazan ( II ), L 3 H 为 3-nitro-1,5-di- p -tolylformazan ( III )) 被合成和表征。化合物I , II , III的分子结构通过 X 射线衍射 (XRD) 确定结晶状态（CIF 文件 CCDC 编号 2161722 ( I )、2167094 ( II ) 和 2167095 ( III )）。根据 XRD 结果和磁性和光谱测量数据，化合物I - III是低自旋钴 (III) 与两个自由基阴离子邻半醌配体和一个甲臜阴离子结合的配合物。配合物在 2–300 K
• Heavy Atom Effect on the Intersystem Crossing of a Boron Difluoride Formazanate Complex‐Based Photosensitizer: Experimental and Theoretical Studies
  作者：Tunyawat Khrootkaew、Sirilak Wangngae、Kantapat Chansaenpak、Kasin Rueantong、Worawat Wattanathana、Piyanut Pinyou、Pannipa Panajapo、Vinich Promarak、Kritsana Sagarik、Anyanee Kamkaew

  DOI：10.1002/asia.202300808

  日期：2024.1.2

  Photodynamic therapy (PDT) is a photochemical‐based treatment approach that involves using light to activate photosensitizers (PSs). Attractively, PDT is one of the alternative cancer treatments due to its noninvasive technique. By utilizing the heavy atom effect, this work modified a class of formazan dyes to improve intersystem crossing (ISC) to improve reactive oxygen species (ROS) generation for PDT treatment. Two methods were used to observe the ROS generation enhanced by ISC of the synthesized complexes including, (1) recording DPBF decomposition caused by the ROS, and (2) calculating the potential energy curves for photophysical mechanisms of BF₂‐formazanate dyes using the DFT and nudged elastic band (NEB) methods. The photophysical properties of the dyes were studied using spectroscopic techniques and X‐ray crystallography, as well as DFT calculations. The experimental and theoretical results and in vitro cellular assays confirmed the potential use of the newly synthesized iodinated BF₂‐formazanate dyes in PDT.

  摘要光动力疗法（PDT）是一种以光化学为基础的治疗方法，包括使用光激活光敏剂（PSs）。光动力疗法是一种基于光化学的治疗方法，它是利用光激活光敏剂（PSs），由于其非侵入性技术，光动力疗法成为癌症治疗的替代方法之一。通过利用重原子效应，这项研究对一类蚁臢染料进行了改良，以改善系统间交叉（ISC），从而改善活性氧（ROS）的生成，用于光致透射疗法。研究采用了两种方法来观察合成复合物的 ISC 对 ROS 生成的促进作用，包括：（1）记录 ROS 引起的 DPBF 分解；（2）使用 DFT 和裸弹带（NEB）方法计算 BF2-甲臢染料光物理机制的势能曲线。利用光谱技术和 X 射线晶体学以及 DFT 计算研究了这些染料的光物理特性。实验和理论结果以及体外细胞检测证实了新合成的碘化 BF2-甲酰肼染料在局部放疗中的潜在用途。