N,N'-bis(5-nitro-salicylidene)hydrazine | 72878-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N'-bis(5-nitro-salicylidene)hydrazine
• 英文别名: 2-[[(2-Hydroxy-5-nitrophenyl)methylidenehydrazinylidene]methyl]-4-nitrophenol
• CAS: 72878-63-8
• 化学式: C₁₄H₁₀N₄O₆
• 分子量: 330.257
• InChiKey: ULNJZDPQMMBRNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 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：
  157
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-bis(5-nitro-salicylidene)hydrazine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以84%的产率得到[N,N'-bis-(2-hydroxy-5-nitrobenzyl)hydrazine]
  参考文献：
  名称：

  Spectroscopic, colorimetric and theoretical investigation of Salicylidene hydrazine based reduced Schiff base and its application towards biologically important anions

  摘要：

  A reduced Schiff base anionic receptor 1 [N,N '-bis-(2-hydroxy-5-nitro-benzyl)hydrazine] has been synthesized, characterized and reported as a selective chromogenic receptor for fluoride, acetate and phosphate anions over the other tested anions such as chloride, bromide, iodide and hydrogensulphite. Colorimetric naked-eye detection and UV-vis absorption spectroscopic techniques were used to distinguish the recognition behaviours towards various anions. The receptor-anion complexation mainly occurs via hydrogen bonding interactions which facile to generate the charge transfer band in the UV-vis spectra and cause large bathochromic shift as well as naked-eye colour change. Complexation stoichiometry, binding constant and free energy change due to complex formation were determined from Benesi-Hildebrand plot. The binding constant and the free energy change values are well interactive for spontaneous complexation. The experimental results have been correlated with the theoretical calculations using B3LYP hybrid functional and 6-311++G(d,p) basis set for both the receptor and complex by Density Functional Theory (DFT) method. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.02.028
• 作为产物：
  描述：

  5-硝基水杨醛 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以91%的产率得到N,N'-bis(5-nitro-salicylidene)hydrazine
  参考文献：
  名称：

  基于聚集体断裂机理的灵敏和选择性的铀酰离子检测

  摘要：

  开发了基于水杨醛嗪衍生物的高选择性荧光传感器，用于检测铀酰阳离子。研究了获得的化合物的聚集诱导的发射特性，并且在有机水性溶剂中聚集后观察到这些衍生物的强发射。发现这些聚集形式的发射被铀酰阳离子有效地淬灭。结果表明，铀酰的作用是破坏性的，而不是促进水杨醛嗪衍生物的聚集。提出了一种破坏聚集体的方法来解释与铀酰阳离子络合对聚集体的破坏。该传感器显示出对铀酰的良好选择性，并且检出限低至ppb级，因此，

  DOI：

  10.1016/j.jphotochem.2018.12.036

文献信息

• A Novel Synthetic Approach to Dichlorostyrenes
  作者：Alexey V Shastin、Vasily N Korotchenko、Valentine G Nenajdenko、Elisabeth S Balenkova

  DOI：10.1016/s0040-4020(00)00606-2

  日期：2000.8

  We found that N-unsubstituted hydrazones of aromatic aldehydes can be easily converted to the corresponding 1,1-dichlorostyrenes in the reaction with carbon tetrachloride using copper (I) chloride as catalyst. Factors affecting the route of the reaction and yields of the products were investigated. A proposed mechanism for the reaction is discussed.

  我们发现，在使用氯化铜（I）作为催化剂与四氯化碳反应中，芳族醛的N-未取代的azo易于转化为相应的1,1-二氯苯乙烯。研究了影响反应路线和产物收率的因素。讨论了提出的反应机理。
• Ruthenium(II)/(III) bipyridine heterochelates incorporating phenolato imine functionalities. Synthesis, crystal structure, spectroscopic and electron-transfer properties and solution reactivities †
  作者：Soma Chakraborty、Mrinalini G. Walawalkar、Goutam Kumar Lahiri

  DOI：10.1039/b001663m

  日期：——

  II) and ruthenium(IV)–ruthenium(III) oxidations in the ranges 0.52–0.77 and 1.71–1.97 V versus SCE respectively. For 1a and 1b, one ligand centred oxidation near 2 V and for all the complexes two bipyridine based reductions have been detected in the ranges −1.51 to −1.56 V and −1.72 to −1.79 V versus SCE. Coulometric oxidation of 1 initially generates the unstable trivalent one-electron paramagnetic

  [Ru（bpy）2（L'）] ClO 4 [py = 2,2'-联吡啶; L'= - OC 6 H 3（R）C（R'）NH; R = R'= H 1a ; R = H，R'= CH 3 1b；R = NO 2，R'= H 1c ]是通过裂解双核的N–N和NC–（脂族和芳族）键合成的亚胺功能。1a的单晶结构确定已验证了1的形成。该复合物在可见光区域表现出很强的MLCT跃迁，在紫外光区域表现出配体内的跃迁，并且在700 nm附近表现出中等强度的发射。量子产率（φ发光处理的）在77 K（乙醇–甲醇，4：1玻璃）在2.2×10 -2 –6.5×10 -3范围内变化，具体取决于1中的L' 。该配合物显示钌（III） -钌（II）和钌（IV） -钌（III）氧化的范围0.52-0.77和1.71-1.97 V相对于 分会分别。对于1a和1b，一个配体 居中 氧化作用 接近2 V，对于所有配合物，两个 联吡啶基于减少已经在范围中检测到-1
• The tautomerization between keto- to phenol-hydrazone induced by anions in the solution
  作者：Xuefang Shang、Jianmei Yuan、Yingling Wang、Jinlian Zhang、Xiufang Xu

  DOI：10.1016/j.molstruc.2011.11.020

  日期：2012.2

  calculation. The addition of F − , AcO − and H 2 PO 4 - to the host solution resulted in a red shift of the charge-transfer absorbance band accompanied by a color change from yellow to orange in the naked-eye experiments. Receptor 1 containing a nitro group at the para position and receptor 2 containing two bromine groups at the ortho and para positions both showed strong binding ability for H 2 PO 4 - ion in

  摘要 两个简单的阴离子受体，2-[(2-hydroxy-5-nitrophenyl)methylene]hydrazone (1) 和 2-[(3,5-dibromo-2-hydroxyphenyl)methylene]hydrazone (2) 与 -OH 结合位点, 被合成和表征。受体 1 和 2 与卤化物阴离子（F - 、Cl - 、Br - 和 I - ）、AcO - 和 H 2 PO 4 - 的阴离子结合能力使用视觉（裸眼）、UV-vis 滴定实验研究干 DMSO 连同 DFT 理论计算。F - 、AcO - 和H 2 PO 4 - 添加到主体溶液中导致电荷转移吸收带红移，并伴随肉眼实验中的颜色从黄色变为橙色。在对位含有硝基的受体1和在邻位和对位含有两个溴基的受体2均表现出对苯酚腙形式的H 2 PO 4 - 离子的强结合能力。此外，由溶液中的阴离子物质诱导的受体1从酮腙转化为苯酚腙的形式。
• Adaptable sensor for employing fluorometric detection of methanol molecules: theoretical aspects and DNA binding studies
  作者：Urmila Saha、Malay Dolai、Gopinatha Suresh Kumar

  DOI：10.1039/c9nj01018a

  日期：——

  The multifunctional ligand NO2-H2SALNN has been synthesized and employed for the selective fluorometric detection of methanol and its interaction with DNA.

  多功能配体NO2-H2SALNN已经合成并用于选择性荧光检测甲醇及其与DNA的相互作用。
• “Test kit” for detection of biologically important anions: A salicylidene-hydrazine based Schiff base
  作者：Sasanka Dalapati、Md Akhtarul Alam、Sankar Jana、Saswati Karmakar、Nikhil Guchhait

  DOI：10.1016/j.saa.2012.10.038

  日期：2013.2

  Test paper coated with Schiff base [(N,N'-bis(5-nitro-salicylidene)hydrazine] receptor 1 (host) can selectively detect fluoride and acetate ions (guest) by developing yellow color which can be detected by naked-eye both in aqueous-acetonitrile solution and in solid supported test kit. UV-vis spectral analysis shows that the absorption peaks at 288 and 345 nm of receptor 1 gradually decrease its initial intensity and new red shifted absorption bands at 397 nm and 455 nm gradually appear upon addition of increasing amount of F- and AcO- ions over several tested anions such as H2PO4-, Cl-, Br-, I-, NO3-, NO2-, HSO4-, HSO3-, and ClO4- in aqueous-acetonitrile solvent. The colorimetric test results and UV-vis spectral analysis are in well agreement with H-1 NMR titration results in d(6)-DMSO solvent. The receptor 1 forms 1:2 stable complexes with F- and AcO- ions. However, similar kind of observation obtained from UV-vis titrations in presence of AcOH corresponds to 1:1 complexation ratio indicating the formation of H-bonding interaction between the receptor and anions (F- and AcO- ions). So, the observed 1:2 complexation ratio can only be explained on the basis of deprotonation (similar to 1 eqv.) and H-bonding (similar to 1 eqv.) interactions [1]. The ratiometric analysis of host-guest complexes corroborates well with the proposed theoretical model optimization at Density Functional Theory (DFT) level. (C) 2012 Elsevier B.V. All rights reserved.