3-cyano-1,5-diphenylformazan | 7014-08-6

• 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-cyano-1,5-diphenylformazan
• 英文别名: 1,5-Diphenyl-3-cyan-formazan；[(E)-Phenyldiazenyl](2-phenylhydrazinylidene)acetonitrile；N'-anilino-1-cyano-N-phenyliminomethanimidamide
• CAS: 7014-08-6
• 化学式: C₁₄H₁₁N₅
• 分子量: 249.275
• InChiKey: ZHYYMTQGXAZLRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 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：
  72.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-cyano-1,5-diphenylformazan 在 氢氧化钾 作用下， 生成 1,5-diphenylformazan-3-carboxylic acid
  参考文献：
  名称：

  Weissbach, Journal fur praktische Chemie (Leipzig 1954), 1903, vol. <2> 67, p. 402

  摘要：

  DOI：
• 作为产物：
  描述：

  偶氮苯六氟磷酸盐 、 α-Cyano-α-phenylhydrazono-o-carboxacetanilide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以50%的产率得到3-cyano-1,5-diphenylformazan
  参考文献：
  名称：

  Khalifa, Mohamed A. E.; Zayed, Ezzat M.; Mohamed, Mona H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 6, p. 552 - 554

  摘要：

  DOI：

文献信息

• Potentiometric, conductimetric, spectrometric, thermogravimetric and magnetic studies of lanthanum complexes with some symmetric 1,5-diaryl-3-cyanoformazans
  作者：N.T. Abdel-Ghani、O.E. Sherif

  DOI：10.1016/0040-6031(89)87172-2

  日期：1989.12

  obtain basic knowledge on the complexes of La(III) with some symmetric 1,5-diaryl-3-cyanoformazans. The ionization constants of the formazans as well as the formation constants of their lanthanum complexes were studied potentiometrically m solution by Sarin's method. The La(III) complexes formed were separated and their structures were elucidated by elemental analysis, IR, NMR spectroscopy, thermogravimetry

  摘要 应用电位、电导、红外、核磁共振、热重和磁化率等多种实验技术来获得La(III)与一些对称1,5-二芳基-3-氰基甲臜络合物的基础知识。甲臜的电离常数及其镧配合物的形成常数通过沙林法在溶液中进行电位测定研究。通过元素分析、红外光谱、核磁共振光谱、热重 (TG)、摩尔电导和磁化率测量，分离出形成的 La(III) 配合物并阐明其结构。
• Microwave-Assisted Synthesis of Arylazoaminopyrazoles as Disperse Dyes for Textile Printing
  作者：Tawfik A. Khattab、Karima M. Haggag、Mohamed H. Elnagdi、Amal A. Abdelrahman、Sherif Abdelmoez Aly

  DOI：10.1002/zaac.201600148

  日期：2016.6

  The synthesis of heterocyclic azo-dyes via conventional heating and microwave (MW) heating was investigated. From a sequence of reactions starting from cyanoacetic acid, 4-arylazo-2H-pyrazol-3-ylamines and 4-arylazo-2-phenyl-2H-pyrazol-3-ylamines were obtained. The structures these compounds were obtained by inspection of spectroscopic and analytical techniques including 1H and 13C NMR spectroscopy

  研究了通过常规加热和微波 (MW) 加热合成杂环偶氮染料。从从氰基乙酸开始的一系列反应中，获得了 4-芳基偶氮-2H-吡唑-3-基胺和 4-芳基偶氮-2-苯基-2H-吡唑-3-基胺。这些化合物的结构是通过检查光谱和分析技术获得的，包括 1H 和 13C NMR 光谱、IR 光谱、质谱和元素分析。研究了这些分散染料在印花涤纶织物中的牢度性能和紫外/可见吸收光谱数据。
• Synthesis and spectral properties of symmetrical and asymmetrical 3-cyano-1,5-diarylformazan dyestuffs for dyeing polyester fabrics
  作者：Tawfik Khattab、Karima M. Haggag

  DOI：10.21608/ejchem.2017.1479.1103

  日期：2017.12.1

  In this study, we report on a general synthetic approach to both symmetrical and asymmetrical 3-cyano-1,5-diarylformazan dyes. The reaction of enaminonitrile with aromatic diazonium salts in slightly acidic medium affords arylhydrazonals as stable intermediate that are readily converted into asymmetrical formazans via second azo-coupling in a weak alkaline medium. Symmetrical formazan dyestuffs are synthesized directly via double azo-coupling of the key intermediate 3-piperidinylacrylonitrile with the corresponding diazonium salts in weak alkaline medium using sodium acetate as a weak base. The structures of the prepared dyestuffs and intermediates are demonstrated by elemental analysis (C, H, N), 1H and 13C NMR, FTIR and GC-MS spectroscopic techniques. The prepared formazan disperse colorants are applied to dye polyester fabric to give satisfactory fastness properties to wash, perspiration, rubbing and light.

  在本研究中，我们报告了一种合成对称和非对称3-氰基-1,5-二芳基福尔马赞染料的普遍合成方法。酰胺氰与芳香族重氮盐在稍微酸性的介质中反应，生成作为稳定中间体的芳基肼醛，这些中间体可以通过在弱碱介质中进行二次偶氮偶联反应，转化为非对称福尔马赞。对称福尔马赞染料则通过将关键中间体3-哌啶基丙烯腈与相应的重氮盐在弱碱性介质中进行双偶氮偶联反应直接合成，采用醋酸钠作为弱碱。通过元素分析（C、H、N）、1H和13C NMR、FTIR和GC-MS光谱技术证明所制备染料和中间体的结构。所制备的福尔马赞分散色料应用于聚酯面料的染色，获得良好的洗涤、汗液、摩擦和光照的牢度性能。
• 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）。
• Structurally Tunable 3-Cyanoformazanate Boron Difluoride Dyes
  作者：Stephanie M. Barbon、Pauline A. Reinkeluers、Jacquelyn T. Price、Viktor N. Staroverov、Joe B. Gilroy

  DOI：10.1002/chem.201404297

  日期：2014.9.1

  The straightforward synthesis of a series of 3‐cyanoformazanate boron difluoride dyes is reported. Phenyl, 4‐methoxyphenyl and 4‐cyanophenyl N‐substituted derivatives were isolated and characterized by single‐crystal X‐ray crystallography, cyclic voltammetry, and UV/Vis spectroscopy. The compounds were demonstrated to possess tunable, substituent‐dependent absorption, emission, and electrochemical

  报道了一系列3-氰基甲氮酸酯二氟化硼染料的直接合成。分离出苯基，4-甲氧基苯基和4-氰基苯基N-取代的衍生物，并通过单晶X射线晶体学，循环伏安法和UV / Vis光谱进行表征。已证明这些化合物具有可调的，取代基依赖性的吸收，发射和电化学性质，可通过电子结构计算对其进行合理化。