2,4-dinitrosalicylaldehydephenylhydrazone | 434328-20-8

• 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: 2,4-dinitrosalicylaldehydephenylhydrazone
• 英文别名: N-(2,4-dinitrophenyl)-N'-(2-hydroxy-1-phenylmethylene) hydrazine；2-[(2,4-dinitro-phenyl)-hydrazonomethyl]-phenol；salicylaldehyde-2,4-nitrophenylhydrazone；(E)-2-((2-(2,4-dinitrophenyl)hydrazono)methyl)phenol；N-(2,4-dinitrophenyl)-N'-[(2-hydroxyphenyl)methylene]hydrazine；(E)-2-((2-(2,4-dinitrophenyl)hydrazineylidene)methyl)phenol；2-Hydroxybenzaldehyde 2,4-dinitrophenylhydrazone；2-[(E)-[(2,4-dinitrophenyl)hydrazinylidene]methyl]phenol
• CAS: 434328-20-8
• 化学式: C₁₃H₁₀N₄O₅
• 分子量: 302.246
• InChiKey: XJOPIKWRRWNIRV-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4-dinitrosalicylaldehydephenylhydrazone 以56%的产率得到
  参考文献：
  名称：

  Kidwai Mazaahir, Bala Renu, Srivastava K. C., Indian J. Chem. B, 33 (1994) N 2, S 193-195

  摘要：

  DOI：
• 作为产物：
  描述：

  水杨醛 、 2,4-二硝基苯肼 以 乙醇 为溶剂， 反应 8.0h， 以86%的产率得到2,4-dinitrosalicylaldehydephenylhydrazone
  参考文献：
  名称：

  一种用于选择性检测水介质中 Zn2+ 的席夫碱发光化学传感器

  摘要：

  基于席夫碱的发光化学传感器由于其易于合成、丰富的光物理特性以及在生物学和材料科学中的潜在应用而引起了极大的研究兴趣。合成并表征了二硝基苯基席夫碱分子探针( L )，以估计其对Zn 2+的选择性检测。由于激发态分子内质子转移 (ESIPT) ，探针L在 DMSO-H 2 O 溶剂混合物中表现出弱发射。有趣的是，在L的 DMSO-H 2 O 溶液中添加 Zn 2+后荧光增强，而随着其他离子的添加​​，发射保持不变。这表明探针L充当 Zn 2+的选择性化学传感器。L : Zn 2+复合物的结合化学计量为1:1，这是使用 Benesi-Hildebrand 图从荧光数据中计算出来的。此外，密度泛函理论 (DFT) 计算也支持绑定模式。结合常数和检测限分别为 6.35 × 10 7 M -1和 1.1 × 10 -8 M。在加入强螯合 EDTA 配体后，L-Zn 2+ 复合物的形成是可逆的。此外，L还可用于检测活

  DOI：

  10.1016/j.molstruc.2022.133310

文献信息

• Synthesis and Spectral Characterization of Hydrazone Schiff Bases Derived from 2,4-Dinitrophenylhydrazine. Crystal Structure of Salicylaldehyde-2,4-Dinitrophenylhydrazone
  作者：Hassan Hosseini Monfared、Omid Pouralimardan、Christoph Janiak

  DOI：10.1515/znb-2007-0515

  日期：2007.5.1

  Reactions of 2,4-dinitrophenylhydrazine with salicylaldehyde, pyridine-2-carbaldehyde and 2- aminobenzophenone in methanol result in the hydrazone Schiff base ligands salicylaldehyde-, pyridine- 2-carbaldehyde-, and 2-aminobenzophenone-2,4-dinitrophenylhydrazone, respectively. Crystals of salicylaldehyde-2,4-dinitrophenylhydrazone are monoclinic, space group P2₁/c, a = 13.820(3), b = 4.3515(9), c = 25.159(7) Å , β = 123.01(2)° with Z = 4. The molecular packing is mostly a zigzag or herring-bone pattern.

  在甲醇中，2,4-二硝基苯肼与水杨醛、2-吡啶甲醛和2-氨基苯基酮反应，分别得到水杨醛-、2-吡啶甲醛-和2-氨基苯基酮-2,4-二硝基苯肼的酰肼席夫碱配体。水杨醛-2,4-二硝基苯肼的晶体属于单斜晶系，空间群P2₁/c，a = 13.820(3) Å，b = 4.3515(9) Å，c = 25.159(7) Å，β = 123.01(2)°，Z = 4。分子排列大多呈锯齿状或鱼骨状。

• Cooperative effect of multiple hydrogen bonding involving the nitro group: solid state dimeric self-assembly of o-, m- and p-hydroxyphenyl-2,4-dinitrophenylhydrazones
  作者：Beata Szczęsna、Zofia Urbańczyk-Lipkowska

  DOI：10.1039/b105498h

  日期：2002.2.11

  involvement of the o-NO2 group oxygen in a new type of intramolecular, resonance-assisted hydrogen-bonded system (RAHB), the phenyl ring has a 2,5-diene geometry. The packing patterns observed in crystals of compounds 1–4 are explained as a result of competition between in-plane hydrogen bonding and inter-planar interactions dominated by π–π stacking and dipole–dipole overlap. FT-IR data confirm aggregation

  的固态研究ø - ，米- ，和p -羟基苯基-2,4- dinitrophenylhydRAzones：1，2，3和4 （3 ·0.5 MeCN中）揭示二聚体自组装分子。两个NH⋯O 2 N和最多六个CH⋯O 2 N分子间氢键的模式会在两个二聚体分子之间产生内聚力。众多弱相互作用的推挽效应会在o -NO 2的带负电的O原子之间产生非键接触组的范围为2.683（2）–2.894（3）Å，远低于范德华半径之和。晶体中OH基团和MeCN分子的存在都不会很大程度地干扰二聚体的形成。为化合物1收集的低温X射线数据提供了证据，表明由于o -NO 2基团氧参与了新型分子内共振辅助氢键系统（RAHB），苯环具有2， 5-二烯的几何形状。在化合物的晶体中观察到的包装模式1 - 4解释是由于平面内氢键和以π-π堆积和偶极-偶极重叠为主的平面间相互作用之间的竞争所致。FT-IR数据证实了溶液中的聚集。讨论了在剑
• SYNTHESIS AND ANTIFUNGAL ACTIVITY OF DIARYL HYDRAZONES FROM 2,4-DINITROPHENYLHYDRAZINE
  作者：SERGIO ORTIZ、RONALD NELSON、VÍCTOR KESTERNICH、MARCIA PÉREZ-FEHRMANN、PHILIPPE CHRISTEN、LAURENCE MARCOURT

  DOI：10.4067/s0717-97072016000300015

  日期：——

  A new series of diarylhydrazones derived from 2,4-dinitrophenylhydrazine were synthesized via condensation with aromatic aldehydes whose structures have been determined by mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectra. Yields were 50-99%. All compounds were screened in vitro for their antifungal activity. Preliminary results indicated that compounds 3g and 3h exhibited promising antifungal potency. Understanding of the structure of these compounds establishes a preliminary structure-activity relationship to form the basis of further investigation.
• Malhotra, Manav; Sharma, Rajiv; Sanduja, Mohit, Acta poloniae pharmaceutica, 2012, vol. 69, # 2, p. 355 - 361
  作者：Malhotra, Manav、Sharma, Rajiv、Sanduja, Mohit、Kumar, Rajeev、Jain, Endra、Deep, Aakash

  DOI：——

  日期：——
• Spectral regression and correlation coefficients of some benzaldimines and salicylaldimines in different solvents
  作者：Hassan H. Hammud、Amer Ghannoum、Mamdouh S. Masoud

  DOI：10.1016/j.saa.2005.04.020

  日期：2006.2

  Sixteen Schiff bases obtained from the condensation of benzaldehyde or salicylaldehyde with various amines (aniline, 4-carboxyaniline, phenlhydrazine, 2,4-dinitrophenylhydrazine, ethylenediamine, hydrazine, o-phenylenediamine and 2,6-pyridinediamine) are studied with UV-vis spectroscopy to observe the effect of solvents, substituents and other structural factors on the spectra. The bands involving different electronic transitions are interpreted. Computerized analysis and multiple regression techniques were applied to calculate the regression and correlation coefficients based on the equation that relates peak position to the solvent parameters that depend on the H-bonding ability, refractive index and dielectric constant of solvents. (c) 2005 Elsevier B.V. All rights reserved.