N,N′-bis(salicyliden)-2,3-diaminopyridine | 189822-35-3

• 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(salicyliden)-2,3-diaminopyridine
• 英文别名: N,N'-disalicylidene-2,3-diaminopyridine；salpyr；2,3-bis(salicylideneamino)pyridine；DAPY-(SalH)2；N,N'-bis(salicylidene)-2,3-diiminopyridine；2,3-H2Salpyr；N,N'-Bis(salicylidene)-2,3-pyridinediamine；2-[[2-[(2-hydroxyphenyl)methylideneamino]pyridin-3-yl]iminomethyl]phenol
• CAS: 189822-35-3
• 化学式: C₁₉H₁₅N₃O₂
• 分子量: 317.347
• InChiKey: GXEPMCSBLUEPPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N′-bis(salicyliden)-2,3-diaminopyridine 以 甲醇 为溶剂， 生成 [Zn(N,N'-bis(salicylidene)-2,3-diiminopyridineato)(phenyltin trichloride)]
  参考文献：
  名称：

  一些新的席夫碱配体与某些过渡金属离子的配合物形成，锌席夫碱配体与某些有机锡氯化物的加合物形成的合成，表征和热力学

  摘要：

  合成了四个新的配合物[M（Salpyr）]，其中Salpyr = N，N'-双（水杨基）-2,3-和3,4-二亚氨基吡啶，M = Co，Cu，Mn，Ni和Zn 1 H NMR，IR光谱，元素分析和紫外可见分光光度法。紫外可见分光光度法研究作为供体与R 2 SnCl 2（R =甲基）形成的锌（II）配合物[Zn（2,3-Salpyr）]和[Zn（3,4-Salpyr）]加合物的形成，苯基，正丁基），PhSnCl 3和Bu 3 SnCl作为受体已在甲醇（作为溶剂）中进行了研究。使用紫外可见分光光度法测量形成常数和热力学自由能。在不同温度下用Zn（II）络合物滴定有机锡氯化物（T = 283–313 K）导致形成1：1加合物。结果表明，随着温度的升高，形成常数减小。R n SnCl 4- n作为受体对给定的锌络合物的反应趋势如下：PhSnCl 3  > Me 2 SnCl 2  > Ph 2 SnCl

  DOI：

  10.1016/j.saa.2012.03.061
• 作为产物：
  描述：

  2,3-二氨基吡啶 、 水杨醛 以 乙醇 为溶剂， 生成 N,N′-bis(salicyliden)-2,3-diaminopyridine
  参考文献：
  名称：

  [2,3-Bis(salicylideneamino-O,N)pyridinato]nickel(II)

  摘要：

  The coordination around the Ni atom in the title compound, {2,2'-[2,3-pyridinediylbis(iminomethyl-N)]diphenolato-O,O')nickel(II), [Ni(C19H13N3O2)], is slightly distorted from square planar. Within the coordination square, the bond angles are in the range 83.8(1)-, 94.8(2)degrees, The Ni-N and Ni-O distances are equal within experimental error, with average values of 1.854(2) and 1,835(2) Angstrom, respectively. Comparison of bond lengths in free and nickel-coordinated ligands indicates a shortening of the C-O bonds due to packing effects. On complex formation, the whole molecule assumes a more planar form, which brings the Ni atoms of neighbouring molecules as close as 3.1908(10) Angstrom to each other.

  DOI：

  10.1107/s0108270197019379

文献信息

• Experimental and theoretical studies on Cu(II) complex of N,N′-disalicylidene-2,3-diaminopyridine ligand reveal indirect evidence for DNA intercalation
  作者：Abdulkadir Kocak、Hakan Yilmaz、Ozlem Faiz、Omer Andac

  DOI：10.1016/j.poly.2015.11.037

  日期：2016.1

  A potential DNA intercalating Cu(II) complex ([CuL]) of the N,N'-disalicylidene-2,3-diaminopyridine ligand (H2L; dianion =L2- has been synthesized and characterized. The photophysical and the DNA binding behaviors of the neutral [CuL] have been investigated both experimentally and theoretically. Experimental studies reveal that the [CuL] has a quite strong interaction with the Calf Thymus DNA (ctDNA) with K-b = (1.53 +/- 0.48) x 10(6). Experimental bathochromism of 4 nm and hypochromism of similar to 50% on the absorption band of the [CuL] at 408 nm by intercalation were reproduced by calculations. The competitive displacement experiments were carried out using Methylene Blue (MB) and Ethidium Bromide (EB). Viscosity measurements totally supported the intercalative interaction. Quantum mechanical calculations using time dependent density functional theory (TDDFT) coupled with polarizable continuum model were carried out in the proposed dimer of deoxyguanosine-monophosphate-deoxycytidine, d(GpC)2, intercalation pocket. The calculations qualitatively confirmed the intercalative binding. In addition, vertical excitation calculations showed that electronic excitations of H2L are affected by the environment and Cu2+ ion. The electronic transitions of the [CuL] are involved in mostly pi-pi* transitions but includes significant contribution from the charge transfer. According to the calculations, the electronic spectrum of the [CuL] is sensitive to the DNA intercalation because of the pi-pi stacking interaction between the DNA base pairs and aromatic rings of the [CuL]. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis, X-ray crystallography, spectroscopy, electrochemistry, thermal and kinetic study of uranyl Schiff base complexes
  作者：Zahra Asadi、Fatemeh Golzard、Vaclav Eigner、Michal Dusek

  DOI：10.1080/00958972.2013.849343

  日期：2013.10.20

  Uranyl(VI) complexes [UO2(L)(solvent)], where L denotes an asymmetric N2O2 Schiff base (salpyr, 3-MeOsalpyr, 4-MeOsalpyr, 5-MeOsalpyr, 5-Clsalpyr or 5-Brsalpyr; salpyr is N,N-bis(salicyliden)-2,3-diaminopyridine), were synthesized and characterized in solution (UV-vis, H-1 NMR, cyclic voltammetry) and in the solid-state (X-ray crystallography, IR, TGA, C H N.). X-ray crystallography of UO2(3-MeOsalpyr) revealed coordination of the uranyl by the tetradentate Schiff base and one disordered solvent, resulting in seven-coordinate uranium. Another disordered solvent was not coordinated. Cyclic voltammetry of [(UO2)-O-VI(L)(solvent)] in acetonitrile was used to investigate the effect of the substituents of the Schiff base ligands on oxidation and reduction potential. The quasi-reversible redox reaction without any successive reactions was accelerated by groups with lesser electron withdrawing. We also investigated the kinetics and mechanism of the exchange reaction of the coordinated solvent with tributylphosphine using spectrophotometric method. The second-order rate constants at four temperatures and activation parameters showed an associative mechanism for all corresponding complexes with the following trend: UO2(5-Clsalpyr)>UO2(5-Brsalpyr)>UO2(3-MeOsalpyr)>UO2(4-MeOsalpyr)>UO2(salpyr)>UO2(5-MeOsalpyr). It was concluded that the steric and electronic properties of the complexes were important for the reaction rate.
• Microwave-Assisted Synthesis of the Tetradentate Schiff-Bases Under Solvent-Free and Catalyst-Free Condition
  作者：Maryam Mirza-Aghayan、Mitra Ghassemzadeh、Maryam Hoseini、Mohammad Bolourtchian

  DOI：10.1081/scc-120015804

  日期：2003.1.4

  Synthesis of tetradentate Shiff bases using microwave activation under solvent-free conditions with and without support is described. This method affords high yields in very short reaction times for synthesis of tetradentate Shiff bases.
• Synthesis and Anti-Bacterial/Catalytic Properties of Schiff Bases and Schiff Base Metal Complexes Derived from 2,3-Diaminopyridine
  作者：T. Jeewoth、H. Li Kam Wah、Minu G. Bhowon、D. Ghoorohoo、K. Babooram

  DOI：10.1080/00945710009351817

  日期：2000.7.1
• Synthesis, characterization, and thermodynamics of some new unsymmetrical Co(III) Schiff base complexes derived from 2,3-diaminopyridine
  作者：Mozaffar Asadi、Susan Torabi、Khosro Mohammadi

  DOI：10.1007/s00706-013-1045-0

  日期：2013.11

  Some new Schiff bases derived from 2,3-diaminopyridine and their new Co(III) complexes were synthesized and characterized. The formation constants of the Co(III) complexes vary according to the following trend: 5-MeO > 5-H > 5-Br and 5-MeO > 3-MeO > 4-MeO. For a given donor, the order of formation constants according to the axial ligand is PBu3 > PPh2Me. The binding trend of the donors toward a given cobalt(III) Schiff base complex is as follows: benzylamine > n-butylamine > sec-butylamine > tert-butylamine; Im > 2-MeIm > 2-EtIm > BzIm; and PBu3 > PPh2Me.