2-((4-nitrophenylimino)methyl)phenol | 788-25-0

• 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-nitrophenylimino)methyl)phenol
• 英文别名: 4-Nitro-N-salicyliden-anilin；N-<2-Hydroxy-benzyliden>-4-nitro-anilin；salicylidene-4-nitroaniline；Salicyliden-p-nitroanilin；2-{[(4-Nitrophenyl)imino]methyl}phenol；2-[(4-nitrophenyl)iminomethyl]phenol
• CAS: 788-25-0
• 化学式: C₁₃H₁₀N₂O₃
• 分子量: 242.234
• InChiKey: OEJXTWLBSDOISG-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  443.4±30.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((4-nitrophenylimino)methyl)phenol 在 sodium sulfite 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 N‑(4‑aminophenyl)salicylidene imine
  参考文献：
  名称：

  Synthesis and spectroscopic properties of a copper(II) binuclear complex of a novel tetradentate asymmetrical Schiff base ligand and its DFT study

  摘要：

  A new asymmetrical Schiff base ligand, N,N'-(salicylidene)-5-bromo-2-hydroxybenzaldehyde-p-phenylenediamine (SBHBP), and its binuclear Cu(II) complex have been synthesized. The molecular structures and spectroscopic properties of the ligand and its complex were experimentally characterized by elemental analysis, FT-IR, NMR and UV-Vis spectroscopic techniques and computationally by the density functional theory (DFT) method. The molecular geometry and vibrational frequencies of the SBHBP ligand in the ground state have been calculated using the B3LYP/6-31G(d,p) and 6-31++G(d,p) basis sets. A potential surface scan study was carried out and the most stable geometry of the SBHBP ligand was confirmed. The calculated results show that the optimized geometry can well reproduce the structural parameters, and the theoretical vibrational frequencies are in good agreement with the experimental values. On calculation of the electronic absorption spectra, TD-DFT calculations were carried out in both the gas and solution phases. The energetic behavior of the SBHBP ligand has been examined in solvent media using the B3LYP method with the 6-31G(d,p) and 6-31++G(d,p) basis sets by applying the Onsager method and polarizable continuum model (PCM). Additionally, Mulliken and NBO atomic charges, NMR analysis, molecular electrostatic potential (MEP) and frontier molecular orbitals (FMO) analysis of the SBHBP ligand were investigated using theoretical calculations. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.10.019
• 作为产物：
  描述：

  苯甲醛 、 4-硝基苯胺 以 乙醇 为溶剂， 反应 3.0h， 生成 2-((4-nitrophenylimino)methyl)phenol
  参考文献：
  名称：

  Fe（III）的羰基释放席夫碱配合物：合成，理化性质，抗微生物和抗癌研究

  摘要：

  摘要 按照简单的湿化学方法合成了释放羰基的席夫碱螯合物衍生的Fe（III）配合物。通过其XRD图谱和FTIR光谱证实了配合物中菱形的配体与金属离子的菱形堆积。通过UV-Vis。，PL，FTIR，XRD和TEM技术对化合物进行表征。通过琼脂圆盘扩散抗菌筛选，在革兰氏阳性和革兰氏阴性细菌上已阐明了该复合物的生物相容性优于纯席夫碱。该复合物在体外也显示出pH响应MTT分析显示，MCF-7乳腺癌细胞具有抗癌作用。CO和席夫碱的释放以及Fe（III）与细胞内线粒体的相互作用是细胞生物相容性的关键因素。这种CORM复合物对MCF-7细胞的抗癌活性高于席夫碱，因此可能成为未来生物医学应用的潜在候选物。 图形摘要 合成了新的Fe（III）的羰基释放CORM-席夫碱配合物。这种释放CO的复合物在水中呈25 ppm浓度时表现出菱形堆积，八面体几何形状并表现出抗菌活性。该复合物具有良好的抗微生物-抗癌潜力。

  DOI：

  10.1007/s12039-020-1746-y

文献信息

• The coordination chemistry of molybdenum and tungsten. Part XIV. Dioxomolybdenum(VI) complexes of bidentate, tridentate, and tetradentate Schiff bases containing oxygen, nitrogen and sulphur donors
  作者：W.E. Hill、N. Atabay、C.A. McAuliffe、F.P. McCullough、S.M. Razzoki

  DOI：10.1016/s0020-1693(00)93414-5

  日期：1979.1

  bidentate, tridentate, tetradentate Schiff base ligands containing oxygen, nitrogen, and sulphur donor atoms have been complexed to the cis-MoO2 moiety. The structures of the resulting complexes are postulated on the basis of infrared and proton n.m.r. arguments previously developed by Yamada. In the case of the complexes of the tetradentate ligands, the nature of the backbone between the imine groups

  含有氧，氮和硫供体原子的大量二齿，三齿，四齿席夫碱配体已与顺式MoO2部分络合。根据山田先前开发的红外和质子核磁共振理论，推测了所得络合物的结构。在四齿配体的配合物的情况下，亚胺基之间的主链的性质决定了发现哪个顺式异构体。
• Syntheses, structures and catalytic properties of ruthenium(II) nitrosyl complexes with bidentate and tetradentate Schiff base ligands
  作者：Fule Wu、Chang-Jiu Wang、Hui Lin、Ai-Quan Jia、Qian-Feng Zhang

  DOI：10.1016/j.ica.2017.12.004

  日期：2018.2

  Abstract Treatment of Ru(NO)Cl3·xH2O with 1 equiv. bidentate Schiff bases in the presence of triethylamine in DMF/THF afforded a series of anionic ruthenium(II) nitrosyl complexes of the type [Et3NH][Ru(κ2-N,O-LR)(NO)Cl3] (HLR = 2-butyliminomethyl-phenol 1, 2-(benzylimino-methyl)-phenol 2, 2-[(4-chloro-phenylimino)-methyl]-phenol 3, 2-[(4-nitro-phenylimino)-methyl]-phenol 4, 2-[(2,6-diisopropyl-ph

  1当量对Ru（NO）Cl3·xH2O的抽象处理 在DMF / THF中在三乙胺存在下的双齿Schiff碱提供了一系列[Et3NH] [Ru（κ2-N，O-LR）（NO）Cl3]类型的阴离子钌（II）亚硝酰基络合物（HLR = 2-丁基亚氨基甲基苯酚1，2-（苄基亚氨基甲基）-苯酚2，2-[（（4-氯-苯基亚氨基）-甲基]-苯酚3，2-[（（4-硝基-苯基亚氨基）-甲基]-苯酚4， 2-[（（2，6-二异丙基-苯基亚氨基）-甲基]-苯酚5）。Ru（NO）Cl3·xH2O与1当量的相互作用 在相同条件下的四齿席夫碱导致分离出阴离子络合物[Et3NH] [Ru（κ2-N，OL-CH2CH2-NOH）-（NO）Cl3]（HL-CH2CH2-NOH = N，N'-二水杨基- 1,2-乙二胺6）和中性络合物[Ru（salen-phn）（NO）Cl]（H2salen-phn = N，N'-二水杨基-1,
• Synthesis, structure and catalytic alcohol oxidation by ruthenium(III) supported by Schiff base and triphenylphosphine ligands
  作者：Li-Hua Tang、Fule Wu、Hui Lin、Ai-Quan Jia、Qian-Feng Zhang

  DOI：10.1016/j.ica.2018.03.017

  日期：2018.5

  tetra-dentate Schiff bases gave corresponding ruthenium(III) complexes [RuCl(PPh3)(salen)] (3) (H2salen = N,N′-disalicylidene-1,2-ethanediamine), [RuCl(PPh3)(salipn)]·2CH2Cl2 (4) (H2salipn = N,N′-disalicylidene-1,2-(1-methyl)ethanediamine), [RuCl(PPh3)(salpn)]·CH2Cl2 (5) (H2salpn = N,N′-disalicylidene-1,2-propanediamine), [RuCl(PPh3)(salphen)]·CH2Cl2 (6) (H2salphen = N,N′-disalicylidene-1,2-phenyldiamine), [R

  用两个当量对[RuCl2（PPh3）3]进行抽象处理。双齿席夫碱N，O-LH-Cl（N，O-LH-Cl = 2 [（3-氯-苯基亚氨基）-甲基]-苯酚）或N，O-LH-NO2（N，O-LH -NO2 = 2 [（（4-硝基-苯基亚氨基）-甲基]-苯酚）在三乙胺的存在下提供顺式-[RuCl（PPh3）（κ2-N，OL-Cl）2]（1）和反式-[RuCl （PPh3）（κ2-N，OL-NO2）2]·Et2O（2）。[RuCl2（PPh3）3]与等当量的反应。四齿席夫碱得到相应的钌（III）络合物[RuCl（PPh3）（salen）]（3）（H2salen = N，N'-二水杨基-1,2-乙二胺），[RuCl（PPh3）（salipn）] ·2CH2Cl2（4）（H2salipn = N，N'-二水杨基-1,2-（1-甲基）乙二胺），[RuCl（PPh3）（salpn）]·CH2Cl2（5）（H2salpn
• Synthesis of Metal Complexes of Schiff Bases and their Nematicidal Activity Against Root Knot Nematode Meloidogyne incognita
  作者：Ekta、Divya Utreja、N. K. Dhillon

  DOI：10.2174/15701786113106660076

  日期：2014.1.20

  non electrolytic on the basis of molar conductance studies. The Schiff bases and their metal complexes had also been screened for their antinemic activity against root knot nematode, Meloidogyne incognita. Complexes have shown significant antinemic activity than their corresponding Schiff bases.

  由Cd（II），Mn（II）和Zn（II）以及配体2-（（3-硝基苯基亚氨基）甲基）苯酚（HL 1）和2-（（4-硝基苯基亚氨基）甲基）苯酚合成六种金属配合物（HL 2）的比例为1：2M。显微分析数据，紫外可见光谱数据，磁化率，IR，1 HNMR，13 CNMR，质量和摩尔电导率测量用于表征配合物的结构。根据摩尔电导研究发现该配合物是非电解的。还对席夫碱及其金属配合物针对根结线虫Meloidogyne incognita的抗肿瘤活性进行了筛选。复合物已显示出比其相应的席夫碱显着的抗肿瘤活性。
• Qualitative Analysis of the Stability of the Oxazine Ring of Various Benzoxazine and Pyridooxazine Derivatives with Proton Nuclear Magnetic Resonance Spectroscopy
  作者：Gerard P. Moloney、David J. Craik、Magdy N. Iskander

  DOI：10.1002/jps.2600810721

  日期：1992.7

  3-benzoxazine and 3,4-dihydro-1,3-pyridooxazine derivatives was synthesized, and the hydrolysis of the derivatives was studied with proton nuclear magnetic resonance spectroscopy. The oxazine derivatives underwent various degrees of hydrolysis when H2O was added to dimethyl sulfoxide solutions of the compounds. The rates and extents of decomposition of the oxazine ring systems depended on the electronic effects

  合成了一系列的3,4-二氢-1,3-苯并恶嗪和3,4-二氢-1,3-吡啶并恶嗪衍生物，并利用质子核磁共振波谱研究了这些衍生物的水解。当将H 2 O加入到化合物的二甲基亚砜溶液中时，恶嗪衍生物经历了不同程度的水解。恶嗪环系统分解的速率和程度取决于分子内取代基的电子效应。对恶嗪分解期间产生的质子核磁共振谱以及恶嗪衍生物的稳定性趋势的研究表明在水解机理中形成了中间体。