N,N'-diacetyl-N-phenyl-p-phenylenediamine | 184154-64-1

• 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,N'-diacetyl-N-phenyl-p-phenylenediamine
• 英文别名: N-phenyl-N,N'-1,4-phenylenebis(acetamide)；N-phenyl-N,N'-(1,4-phenylene)diacetamide；N-(4-acetamidophenyl)-N-phenylacetamide；p-(N-Acetylanilino)-acetanilid；N-[4-(N-acetylanilino)phenyl]acetamide
• CAS: 184154-64-1
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: OFFMWWQWZTYYOX-UHFFFAOYSA-N

物化性质

• 沸点：
  578.2±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-diacetyl-N-phenyl-p-phenylenediamine 在 sodium hydroxide 、 copper(l) iodide 、 potassium carbonate 、 lead dioxide 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 72.25h， 生成 1-N-phenyl-4-N-[3-[(4-phenyliminocyclohexa-2,5-dien-1-ylidene)amino]phenyl]cyclohexa-2,5-diene-1,4-diimine
  参考文献：
  名称：

  Stable Triplet-State Di(Cation Radicals) of a Meta−Para Aniline Oligomer by “Acid Doping”

  摘要：

  We describe the formation of a stable triplet-state oligoaniline di(cation radical) via a proton-triggered odor reaction between N,N'-bis[4-(phenylamino)phenyl]-1,3-benzenediamine (1) and N,N'-bis[4-(phenylimino)cyclohexa-2,5-dienylidene]-1,3-benzenediamine (2). In this reaction 1 is oxidized, while protonated 2 is reduced, both yielding the same di(cation radical) 1(2 . 2+). The di(cation radical) is characterized with UV/visisble/near-IR and ESR spectroscopy (D = 118 MHz; E approximate to 0 MHz). Variable-temperature ESR measurements are consistent with a triplet ground state fur 1(2 . 2+), The high stability of 1(2 . 2+) under ambient conditions demonstrates that alternating meta and para oligoanilines are interesting building blocks for future polaronic ferromagnets.

  DOI：

  10.1021/ja9616591
• 作为产物：
  描述：

  N-乙酰苯胺 在 ammonium peroxydisulfate 、 copper diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以52%的产率得到N,N'-diacetyl-N-phenyl-p-phenylenediamine
  参考文献：
  名称：

  经由自由基途径的苯甲酸酯的对位选择性铜催化的C（sp2）-H酰胺化/二聚。

  摘要：

  通过区域选择性的C（sp2）-H功能化实现了铜催化的苯甲酰胺的酰胺化/二聚化。在过硫酸铵作为铜催化剂的自由基源/氧化剂的情况下，通过导致CN键形成的自由基途径，在苯胺芳环上完成对选择酰胺化。所开发的方案可耐受多种苯胺基体。区域选择性通过单晶X射线研究证实。

  DOI：

  10.1039/c9cc09824k

文献信息

• Design, synthesis and characterization of novel nitrogen- and sulfur-containing polymers with well-defined conjugated length
  作者：Kaizheng Zhu、Lixiang Wang、Xiabin Jing、Fosong Wang

  DOI：10.1039/b105628j

  日期：2002.1.24

  A series of novel nitrogen- and sulfur-containing conjugated polymers with well-defined conjugation length have been synthesized via an acid-induced self-polycondensation of functional monomers with methylsulfinyl groups. Synthesized polymers exhibit good solubility in common solvents, such as CHCl3, THF, DMF, DMSO, and NMP. With increased numbers of aminophenyl groups, these polymers have shown similar electrical properties to polyaniline (PAn), and these are demonstrated by UV–vis spectroscopy and cyclic voltammetry (CV) measurements on the polymers. The conductivity of preliminarily protonic-doped poly[phenylene sulfide-alt-tetrakis(aniline)] (PPSTEA) is up to 10−1 S cm−1.

  通过功能单体与甲基亚磺酰基的酸诱导自缩聚反应，合成了一系列具有明确共轭长度的新型含氮和硫共轭聚合物。合成的聚合物在常见溶剂中表现出良好的溶解度，例如CHCl3、THF、DMF、DMSO和NMP。随着氨基苯基数量的增加，这些聚合物表现出与聚苯胺 (PAn) 相似的电性能，这些性能通过聚合物的紫外可见光谱和循环伏安法 (CV) 测量得到了证明。初步质子掺杂的聚[苯硫醚-alt-四(苯胺)] (PPSTEA) 的电导率高达 10−1 S cm−1。
• Generation of a triplet diradical from a donor–acceptor cross conjugate upon acid-induced electron transfer
  作者：Mats O. Sandberg、Osami Nagao、Zhikun Wu、Michio M. Matsushita、Tadashi Sugawara

  DOI：10.1039/b804999h

  日期：——

  Enhancement of the electron acceptor ability of a para-quinodiimine unit by double protonation leads to the proton-induced intramolecular electron transfer from the donor unit to the cross-conjugated acceptor, giving rise to ground state triplet diradical reversibly.

  通过双质子化增强对喹啉二亚胺单元的电子受体能力导致质子诱导的分子内电子从供体单元转移至交叉共轭受体，从而可逆地产生基态三重态双自由基。
• <i>para</i>-Selective copper-catalyzed C(sp²)–H amidation/dimerization of anilides <i>via</i> a radical pathway
  作者：Amol B. Viveki、Dnyaneshwar N. Garad、Rajesh G. Gonnade、Santosh B. Mhaske

  DOI：10.1039/c9cc09824k

  日期：——

  Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp2)-H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C-N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The

  通过区域选择性的C（sp2）-H功能化实现了铜催化的苯甲酰胺的酰胺化/二聚化。在过硫酸铵作为铜催化剂的自由基源/氧化剂的情况下，通过导致CN键形成的自由基途径，在苯胺芳环上完成对选择酰胺化。所开发的方案可耐受多种苯胺基体。区域选择性通过单晶X射线研究证实。
• Stable Triplet-State Di(Cation Radicals) of a <i>Meta</i><i>−</i><i>Para</i> Aniline Oligomer by “Acid Doping”
  作者：Martijn M. Wienk、René A. J. Janssen

  DOI：10.1021/ja9616591

  日期：1996.1.1

  We describe the formation of a stable triplet-state oligoaniline di(cation radical) via a proton-triggered odor reaction between N,N'-bis[4-(phenylamino)phenyl]-1,3-benzenediamine (1) and N,N'-bis[4-(phenylimino)cyclohexa-2,5-dienylidene]-1,3-benzenediamine (2). In this reaction 1 is oxidized, while protonated 2 is reduced, both yielding the same di(cation radical) 1(2 . 2+). The di(cation radical) is characterized with UV/visisble/near-IR and ESR spectroscopy (D = 118 MHz; E approximate to 0 MHz). Variable-temperature ESR measurements are consistent with a triplet ground state fur 1(2 . 2+), The high stability of 1(2 . 2+) under ambient conditions demonstrates that alternating meta and para oligoanilines are interesting building blocks for future polaronic ferromagnets.

表征谱图