N-(2,4-dichlorophenyl)sulfanyl-4-nitro-2,6-diphenylaniline | 203051-51-8

• 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: N-(2,4-dichlorophenyl)sulfanyl-4-nitro-2,6-diphenylaniline
• CAS: 203051-51-8
• 化学式: C₂₄H₁₆Cl₂N₂O₂S
• 分子量: 467.375
• InChiKey: AKEVKKVNPDREPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,4-dichlorophenyl)sulfanyl-4-nitro-2,6-diphenylaniline 在 potassium carbonate 、 lead dioxide 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Stable Thioaminyl Radicals Having Functional Groups:  Generation, ESR Spectra, Isolation, X-ray Crystallographic Analyses, and Magnetic Characterization of N-(Arylthio)-4-(ethoxycarbonyl)-2,6-diarylphenylaminyls, N-(Arylthio)-4-acetyl-2,6-diarylphenylaminyls, and N-(Arylthio)-4-cyano-2,6-diarylphenylaminyls¹

  摘要：

  Oxidation of N-(arylthio)-4-(ethoxycarbonyl)-2,6-diarylanilines (9), N-(arylthio)-4-acetyl-2,6-diarylanilines (10), and N-(arylthio)-4-cyano-2,6-diarylanilines (11) with PbO2 yielded quite persistent N-(arylthio)-4-(ethoxycarbonyl)-2,6-diarylphenylaminyls (4), N-(arylthio)-4-acetyl-2,6-diarylphenylaminyls (5), and N-(arylthio)-4-cyano-2,6-diarylphenylaminyls (6), respectively, and they were isolated as pure radical crystals. On the other hand, N-(arylthio)-4-nitro-2,6-diarylphenylaminyls (6), and N-(arylthio)-4-chloro-2,6-diarylphenylaminyls (7), were unstable and soon decomposed. The X-ray crystallographic analyses of N-[(2,4-dichlorophenyl)thio]-4-acetyl-2, diphenylphenylaminyl (5c) and N-[(2,4-dichlorophenyl)thio]-4-cyano-2,6-diphenylphenylaminyl (6c) showed that the Ph-N-S-Ph pi-framework is planar, and the 2- and 6-phenyl groups are twisted from the coplane. The ESR studies for 4-8 showed that their hyperfine coupling constants are nearly identical to each other and that the unpaired electron is extensively delocalized onto the anilino benzene ring and the arylthiyl group. The magnetic susceptibility measurements were carried out for five thioaminyl radical crystals and showed that one radical couples ferromagnetically with 2J/k(B) = 16.0 K, and the other four radicals couple antiferromagnetically with 2J/k(B) = -15.6 to -194.6 K or theta = -0.6 to -5.0 K.

  DOI：

  10.1021/jo9718206
• 作为产物：
  描述：

  2,6-二溴-4-硝基苯胺 在 四(三苯基膦)钯 、 sodium carbonate 、 三乙胺 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 N-(2,4-dichlorophenyl)sulfanyl-4-nitro-2,6-diphenylaniline
  参考文献：
  名称：

  Stable Thioaminyl Radicals Having Functional Groups:  Generation, ESR Spectra, Isolation, X-ray Crystallographic Analyses, and Magnetic Characterization of N-(Arylthio)-4-(ethoxycarbonyl)-2,6-diarylphenylaminyls, N-(Arylthio)-4-acetyl-2,6-diarylphenylaminyls, and N-(Arylthio)-4-cyano-2,6-diarylphenylaminyls¹

  摘要：

  Oxidation of N-(arylthio)-4-(ethoxycarbonyl)-2,6-diarylanilines (9), N-(arylthio)-4-acetyl-2,6-diarylanilines (10), and N-(arylthio)-4-cyano-2,6-diarylanilines (11) with PbO2 yielded quite persistent N-(arylthio)-4-(ethoxycarbonyl)-2,6-diarylphenylaminyls (4), N-(arylthio)-4-acetyl-2,6-diarylphenylaminyls (5), and N-(arylthio)-4-cyano-2,6-diarylphenylaminyls (6), respectively, and they were isolated as pure radical crystals. On the other hand, N-(arylthio)-4-nitro-2,6-diarylphenylaminyls (6), and N-(arylthio)-4-chloro-2,6-diarylphenylaminyls (7), were unstable and soon decomposed. The X-ray crystallographic analyses of N-[(2,4-dichlorophenyl)thio]-4-acetyl-2, diphenylphenylaminyl (5c) and N-[(2,4-dichlorophenyl)thio]-4-cyano-2,6-diphenylphenylaminyl (6c) showed that the Ph-N-S-Ph pi-framework is planar, and the 2- and 6-phenyl groups are twisted from the coplane. The ESR studies for 4-8 showed that their hyperfine coupling constants are nearly identical to each other and that the unpaired electron is extensively delocalized onto the anilino benzene ring and the arylthiyl group. The magnetic susceptibility measurements were carried out for five thioaminyl radical crystals and showed that one radical couples ferromagnetically with 2J/k(B) = 16.0 K, and the other four radicals couple antiferromagnetically with 2J/k(B) = -15.6 to -194.6 K or theta = -0.6 to -5.0 K.

  DOI：

  10.1021/jo9718206

文献信息

• Stable Thioaminyl Radicals Having Functional Groups:  Generation, ESR Spectra, Isolation, X-ray Crystallographic Analyses, and Magnetic Characterization of <i>N</i>-(Arylthio)-4-(ethoxycarbonyl)-2,6-diarylphenylaminyls, <i>N</i>-(Arylthio)-4-acetyl-2,6-diarylphenylaminyls, and <i>N</i>-(Arylthio)-4-cyano-2,6-diarylphenylaminyls¹
  作者：Yozo Miura、Masayoshi Momoki、Masaaki Nakatsuji、Yoshio Teki

  DOI：10.1021/jo9718206

  日期：1998.3.1

  Oxidation of N-(arylthio)-4-(ethoxycarbonyl)-2,6-diarylanilines (9), N-(arylthio)-4-acetyl-2,6-diarylanilines (10), and N-(arylthio)-4-cyano-2,6-diarylanilines (11) with PbO2 yielded quite persistent N-(arylthio)-4-(ethoxycarbonyl)-2,6-diarylphenylaminyls (4), N-(arylthio)-4-acetyl-2,6-diarylphenylaminyls (5), and N-(arylthio)-4-cyano-2,6-diarylphenylaminyls (6), respectively, and they were isolated as pure radical crystals. On the other hand, N-(arylthio)-4-nitro-2,6-diarylphenylaminyls (6), and N-(arylthio)-4-chloro-2,6-diarylphenylaminyls (7), were unstable and soon decomposed. The X-ray crystallographic analyses of N-[(2,4-dichlorophenyl)thio]-4-acetyl-2, diphenylphenylaminyl (5c) and N-[(2,4-dichlorophenyl)thio]-4-cyano-2,6-diphenylphenylaminyl (6c) showed that the Ph-N-S-Ph pi-framework is planar, and the 2- and 6-phenyl groups are twisted from the coplane. The ESR studies for 4-8 showed that their hyperfine coupling constants are nearly identical to each other and that the unpaired electron is extensively delocalized onto the anilino benzene ring and the arylthiyl group. The magnetic susceptibility measurements were carried out for five thioaminyl radical crystals and showed that one radical couples ferromagnetically with 2J/k(B) = 16.0 K, and the other four radicals couple antiferromagnetically with 2J/k(B) = -15.6 to -194.6 K or theta = -0.6 to -5.0 K.