4-iodo-N-(4-nitrobenzylidene)aniline | 3382-81-8

• 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: 4-iodo-N-(4-nitrobenzylidene)aniline
• 英文别名: 4-Iodo-N-[(E)-(4-nitrophenyl)methylidene]aniline；N-(4-iodophenyl)-1-(4-nitrophenyl)methanimine
• CAS: 3382-81-8
• 化学式: C₁₃H₉IN₂O₂
• mdl: MFCD00441525
• 分子量: 352.131
• InChiKey: UPTYSJVCCLVCPK-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C(Solv: ethanol (64-17-5))
• 沸点：
  452.7±30.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-iodo-N-(4-nitrobenzylidene)aniline 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 4-iodo-N-(4-nitrobenzyl)aniline
  参考文献：
  名称：

  Isomeric iodo-N-(nitrobenzyl)anilines: interplay of hard and soft hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions

  摘要：

  2-碘-N-(4-硝基苄基)苯胺分子 4-O2NC6H4CH2NHC6H4I-2′ (1) 通过 C-H...O 氢键连接成链。在异构化合物 3-碘-N-（4-硝基苄基）苯胺（2）中，N-H...O 和 C-H...O 氢键以及碘...硝基和芳香族 π...π 堆积相互作用将分子连接成一个三维框架结构。4-iodo-N-(4-nitrobenzyl)aniline (6) 的二维超分子结构由 C-H...O 和 N-H...π(arene)氢键以及芳香族 π...π 堆积相互作用组合而成。2-碘-N-（2-硝基苄基）苯胺（7）结晶时不对称单元中有两个分子，这些分子通过 N-H...O、C-H...O 氢键以及碘...硝基和芳香族 π...π 堆积相互作用连接成梯状。从特定方向的分子间相互作用类型和所产生的超分子结构的维度两方面，对这些化合物的超分子结构和其他异构体的超分子结构进行了比较。

  DOI：

  10.1107/s0108768104012017
• 作为产物：
  描述：

  对硝基苯甲醛 、 对碘苯胺 在 molecular sieve 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以83%的产率得到4-iodo-N-(4-nitrobenzylidene)aniline
  参考文献：
  名称：

  从对硝基苯甲醛衍生的具有生物活性的新席夫碱的合成，光谱和细胞毒性研究。

  摘要：

  通过与适当的胺缩合，合成了十三种衍生自对硝基苯甲醛的新席夫碱。在一个反应​​中也观察到对硝基苯甲醛向相应的醇的不寻常还原。使用光谱技术鉴定化合物的结构。研究了标题化合物对用作试验动物的盐水虾的细胞毒性。

  DOI：

  10.1248/cpb.55.1070

文献信息

• Non-linear photo-switching in molecular actuators through intra-molecular energy transfer from an electron donating core
  作者：Óscar Guzmán-Méndez、Emmanuel Villatoro、Mariana M. Reza、Maria Eugenia Sandoval、Jesus Jara-Cortés、Martha Elena García-Aguilera、Melissa Bravo-Romero、José G. López-Cortés、Jorge Peon

  DOI：10.1039/d3tc00969f

  日期：——

  mechanism where the formation of the actuator-localized 1nπ* states is directly followed by the azo-isomerization reactions. Computational studies at the TD-DFT level of theory, together with the use of a quadratic response method were used to characterize the states responsible for the two-photon absorption properties. This kind of molecular assembly can be extended to induce non-linear photochemistry

  我们提出了一种多发色分子的新设计，其中中央供电子核的非线性吸收特性用于赋予分子致动器间接双光子吸收特征。这种设计提供了一种向分子系统提供双光子反应性的通用方法，而分子系统本身无法通过非线性光学输入进行控制。该化合物基于双光子活性N , N '-1,4-二氢吡咯并[3,2- b]吡咯中心单元。该核心在其长轴末端被硝基苯基对称取代，定义了伪中心对称的受体-供体-受体（A-D-A）天线单元。对于第一个概念验证研究，偶氮异构化执行器通过杂环核的氮原子键合到中心单元。这种设计允许吡咯-吡咯发色团充当非线性吸收单元，因此E – Z在激发到位于中心单元的更高状态后，可以引起致动器的异构化，然后能量转移到受体局部激发态。使用来自钛蓝宝石激光器的脉冲近红外光观察致动器的非线性异构化，该装置允许致动器异构化产物在宏观样品中显着积累。我们证明了致动器的双光子光化学是由于与中央核心单元的耦合，因为单独的偶氮致动器
• Mercuration of Schiff bases of substituted benzylideneanilines
  作者：Kuiling Ding、Yangjie Wu、Hongwen Hu、Lianfang Shen、Xin Wang

  DOI：10.1021/om00059a058

  日期：1992.11

  As part of an effort to investigate substituent effects on the intramolecular coordination between N and Hg, the mercuration of 36 substituted benzylideneanilines was studied. The structure characterization of the products by IR, H-1 NMR, C-13 NMR, and MS indicates that for all of the reactions examined, the mercury is directed to the ortho position of the N-phenyl ring or the para position of the N-phenyl ring when these sites are not occupied by a substituent. The position of the HgCl group in the mercurated product of N-(4-nitrobenzylidene)-beta-naphthylamine has been confirmed by single-crystal X-ray determination, which also provided circumstantial evidence for the existence of the N--> Hg intramolecular coordination with a four-membered ring. The possible mechanism of the reaction was proposed, in which the mercuration at the ortho position of the N-phenyl ring was facilitated by the imino moiety upon formation of a coordination complex with Hg(OAc)2 in the first step, followed by a subsequent electrophilic substitution at the ortho position of the N-phenyl ring. This reaction is different from the metalation of benzylideneanilines by transition metals, in which the metal atom is usually directed to the ortho position of the C-phenyl ring, and provides a new example of the so-called 'cyclometalation" reaction.
• Diurno; Mazzoni; Piscopo, Il Farmaco, 1992, vol. 47, # 2, p. 239 - 247
  作者：Diurno、Mazzoni、Piscopo、Bolognese

  DOI：——

  日期：——
• Synthesis, Spectroscopic and Cytotoxic Studies of Biologically Active New Schiff Bases Derived from p-Nitrobenzaldehyde
  作者：Amjid Iqbal、Hamid Latif Siddiqui、Chaudhary Muhammad Ashraf、Mujahid Hussain Bukhari、Chaudhary Muhammad Akram

  DOI：10.1248/cpb.55.1070

  日期：——

  Thirteen new Schiff bases derived from p-nitrobenzaldehyde were synthesized by condensation with the appropriate amines. An unusual reduction of the p-nitrobenzaldehyde to the corresponding alcohol was also observed in one of the reactions. The structures of the compounds were identified using spectroscopic techniques. Cytotoxicity for the titled compounds was studied against Brine Shrimp, used as

  通过与适当的胺缩合，合成了十三种衍生自对硝基苯甲醛的新席夫碱。在一个反应​​中也观察到对硝基苯甲醛向相应的醇的不寻常还原。使用光谱技术鉴定化合物的结构。研究了标题化合物对用作试验动物的盐水虾的细胞毒性。
• Isomeric iodo-<i>N</i>-(nitrobenzyl)anilines: interplay of hard and soft hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions
  作者：Christopher Glidewell、John N. Low、Janet M. S. Skakle、Solange M. S. V. Wardell、James L. Wardell

  DOI：10.1107/s0108768104012017

  日期：2004.8.1

  Molecules of 2-iodo-N-(4-nitrobenzyl)aniline, 4-O₂NC₆H₄CH₂NHC₆H₄I-2′ (1) are linked into chains by C—H...O hydrogen bonds. In the isomeric compound 3-iodo-N-(4-nitrobenzyl)aniline (2) a combination of N—H...O and C—H...O hydrogen bonds and iodo...nitro and aromatic π...π stacking interactions links the molecules into a three-dimensional framework structure. The two-dimensional supramolecular structure of 4-iodo-N-(4-nitrobenzyl)aniline (6) is built from a combination of C—H...O and N—H...π(arene) hydrogen bonds and aromatic π...π stacking interactions. 2-Iodo-N-(2-nitrobenzyl)aniline (7) crystallizes with two molecules in the asymmetric unit and these molecules are linked into ladders by a combination of N—H...O and C—H...O hydrogen bonds and iodo...nitro and aromatic π...π stacking interactions. Comparisons are made between the supramolecular structures of these compounds and those of other isomers, in terms both of the types of direction-specific intermolecular interactions exhibited and the dimensionality of the resulting supramolecular structures.

  2-碘-N-(4-硝基苄基)苯胺分子 4-O2NC6H4CH2NHC6H4I-2′ (1) 通过 C-H...O 氢键连接成链。在异构化合物 3-碘-N-（4-硝基苄基）苯胺（2）中，N-H...O 和 C-H...O 氢键以及碘...硝基和芳香族 π...π 堆积相互作用将分子连接成一个三维框架结构。4-iodo-N-(4-nitrobenzyl)aniline (6) 的二维超分子结构由 C-H...O 和 N-H...π(arene)氢键以及芳香族 π...π 堆积相互作用组合而成。2-碘-N-（2-硝基苄基）苯胺（7）结晶时不对称单元中有两个分子，这些分子通过 N-H...O、C-H...O 氢键以及碘...硝基和芳香族 π...π 堆积相互作用连接成梯状。从特定方向的分子间相互作用类型和所产生的超分子结构的维度两方面，对这些化合物的超分子结构和其他异构体的超分子结构进行了比较。