4-acetyl-2,6-di(phenyl-d5)aniline | 501422-70-4

• 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: 4-acetyl-2,6-di(phenyl-d5)aniline
• 英文别名: 1-[4-Amino-3,5-bis(2,3,4,5,6-pentadeuteriophenyl)phenyl]ethanone
• CAS: 501422-70-4
• 化学式: C₂₀H₁₇NO
• 分子量: 297.282
• InChiKey: HTVKHRVZKDMNJY-WRZMZMNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-acetyl-2,6-di(phenyl-d5)aniline 在 potassium carbonate 、 lead dioxide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 2.0h， 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：

  4-氨基-3,5-二溴苯乙酮 、 苯基-D5-硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 14.0h， 以67%的产率得到4-acetyl-2,6-di(phenyl-d5)aniline
  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

• Magnetic Interaction of Pyridyl-Substituted Thioaminyl Stable Free Radicals¹
  作者：Yozo Miura、Yuichi Oyama、Yoshio Teki

  DOI：10.1021/jo0205659

  日期：2003.2.1

  as radical crystals. Their ESR spectra were measured, and the NS and pyridyl nitrogen and anilino meta and pyridyl ortho and para proton hyperfine coupling constants were determined. The spin-density calculations based on the density functional theory were performed by the UBecke 3LYP hybrid method using the STO 6-31G basis set. X-ray crystallographic analyses were performed for three radicals, and

  N-（2-吡啶硫基）-2,6-二芳基-4-R-苯胺基（R = Ph，4-ClC（6）H（4），MeCO，CN，EtOCO）和N-（4-吡啶硫基）-制备2,6-二芳基-4-R-苯胺基（R = Ph，4-ClC（6）H（4），EtOCO）并分离为自由基晶体。测量了它们的ESR谱，并测定了NS和吡啶基氮以及苯胺基间和吡啶基邻和对质子的超精细耦合常数。基于密度泛函理论的自旋密度计算是通过UBecke 3LYP混合方法，使用STO 6-31G基集进行的。对三个自由基进行了X射线晶体学分析，并详细讨论了它们的结构。用SQUID磁力计对9种离析的自由基进行磁化率测量。一个基团显示出铁磁耦合（2J / k（B）= 44 K），其他显示反铁磁行为。根据晶体结构解释了观察到的磁相互作用。
• 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.