苯甲酸,4-[(2-吡啶基亚甲基)氨基]- | 13160-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯甲酸,4-[(2-吡啶基亚甲基)氨基]-
• 英文名称: 4-[(2-pyridinylmethylene)amino]benzoic acid
• 英文别名: 4-N-(2'-pyridylimine)benzoic acid；N-(pyrid-2-ylmethylene)-p-COOH-phenylamine；4-[2]pyridylmethylenamino-benzoic acid；4-[2]Pyridylmethylenamino-benzoesaeure
• CAS: 13160-73-1
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: FATACTPSTUQJDC-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.55
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  苯甲酸,4-[(2-吡啶基亚甲基)氨基]- 、 cobalt(II) perchlorate hexahydrate 在 KOH 作用下， 以 乙醇 为溶剂， 以57%的产率得到(Co(4-N-(2'-pyridylimine)benzoate)2(H2O))(H3O)(ClO4)
  参考文献：
  名称：

  Synthesis, Crystal Structure, and Characterization of a Novel One-Dimensional Helical Chain Cobalt(II) Coordination Polymer

  摘要：

  A novel one-dimensional (1D) helical chain polymer, {[CoL2(H2O)](H3O)(ClO4)}(n) (1) (HL = 4-N-(2'-pyridylimine)benzoic acid), was synthesized by reaction of Co(II) perchlorate with L anion in ethanol solution, and characterized by element analyses, infrared spectroscopy, and X-ray single-crystal diffraction. In this structure, the Co2+ ion is in a distorted octahedral geometry, an infinite 1D helical chain was constructed by L ligand through bidentate-monodentate bridging modes and are further assembled into three-dimensional supramolecular networks through complicated O-H center dot center dot center dot Ohydrogen bonding interactions.

  DOI：

  10.1080/15533174.2011.613081
• 作为产物：
  描述：

  吡啶-2-甲醛 、 对氨基苯甲酸 在 乙醇 作用下， 生成 苯甲酸,4-[(2-吡啶基亚甲基)氨基]-
  参考文献：
  名称：

  Synthese einiger neuer Hydrazone des Cyanessigsäurehydrazids und Isonicotinsäurehydrazids. 8. Mitteilung über Synthese tuberkulostatischer Substanzen

  摘要：

  DOI：

  10.1002/ardp.19562890404

文献信息

• Sticky complexes: carboxylic acid-functionalized N-phenylpyridin-2-ylmethanimine ligands as anchoring domains for copper and ruthenium dye-sensitized solar cells
  作者：Biljana Bozic-Weber、Edwin C. Constable、Catherine E. Housecroft、Markus Neuburger、Jason R. Price

  DOI：10.1039/b925623g

  日期：——

  Four members of a series of N-phenylpyridin-2-ylmethanimine ligands (L) decorated with carboxylic acid functionalities have been prepared. The ligand design allows a copper(I) complex [CuL2]+ to bind to a TiO2 surface through the simultaneous use of two carboxylate anchoring domains. Complexes of the type [CuL2][PF6], [CuL(NCMe)2][PF6] and [Ru(bpy)2L][PF6]2 have been synthesized and characterized by 1H and 13C NMR and electronic absorption spectroscopies, mass spectrometry and, for four of the complexes, single crystal X-ray diffraction. Dye-sensitized solar cells (DSCs) have been fabricated using the new complexes and the performances of the dyes assessed. The copper(I) complexes show good surface coverage and tuning of the electrolyte and the electronic properties of the ligands is now required to enhance the efficiencies of the DSCs.

  我们制备了一系列具有羧酸官能团装饰的 N-苯基吡啶-2-基甲亚胺配体（L）的四个成员。配体设计通过同时使用两个羧酸盐锚定结构域，使铜（I）配合物 [CuL2]+ 与二氧化钛表面结合。我们合成了[CuL2][PF6]、[CuL(NCMe)2][PF6]和[Ru(py)2L][PF6]2等类型的配合物，并通过 1H、13C NMR 和电子吸收光谱、质谱以及其中四个配合物的单晶 X 射线衍射进行了表征。利用这些新络合物制作了染料敏化太阳能电池（DSC），并对染料的性能进行了评估。铜（I）配合物显示出良好的表面覆盖性，现在需要调整电解质和配体的电子特性，以提高 DSC 的效率。
• Synthesis and structural characterization of heteroleptic Cu(I) perchlorate complexes with diimines derived from pyridinyliminobenzoic acids
  作者：S. Shakhatreh、J. Mohanraj、A. Czapik、D. Tzimopoulos、S. Kotoulas、M. Gdaniec、P.D. Akrivos

  DOI：10.1016/j.molstruc.2011.06.044

  日期：2011.9

  tetrahedral environment of the metal is completed by the coordination of two triphenylphosphane molecules. The compounds with the mono-substituted ligands crystallize as dimers via hydrogen bonds between the carboxylic groups. The electronic absorption spectra are dominated by the intraligand bands while characteristic charge transfer transitions are observed in the region 360–500 nm. The complexes proved

  摘要 三种通式为[Cu(L)(PPh3)2][ClO4]的杂配单价铜配合物的合成及分子电子结构研究，其中L分别为3-,4-吡啶基亚氨基和3,5-二吡啶基亚氨基分别报道了取代的苯甲酸。配合物的晶体结构揭示了金属与配体的二亚胺位点的配位。金属的四面体环境由两个三苯基膦分子的配位完成。具有单取代配体的化合物通过羧基之间的氢键结晶为二聚体。电子吸收光谱由内配体带支配，而在 360-500 nm 区域观察到特征电荷转移跃迁。证明复合物在室温和低温（77 K 刚性基质）下都是弱发射体。这种光致发光的缺乏不能归因于 Cu(I) 金属核的容易氧化，因为它们的循环伏安法研究显示 E1/2 值高于 1.0 V，而是由于配位环境的灵活性，在氧化时会发生重组。
• Pentamethylcyclopentadienyl ruthenium(II) complexes of para-substituted N-(pyrid-2-ylmethylene)-phenylamine ligands: syntheses, spectral and structural studies
  作者：Keisham Sarjit Singh、Patrick J. Carroll、Mohan Rao Kollipara

  DOI：10.1016/j.poly.2004.11.021

  日期：2005.2

  of [(η5-C5Me5)Ru(PPh3)2Cl] (1) with acetonitrile in the presence of excess NH4PF6 leads to the formation of the cationic ruthenium(II) complex [(η5-C5Me5)Ru(PPh3)2(CH3CN)]PF6 (2). The complex (2) reacts with a series of N,N′ donor Schiff base ligands viz. para-substituted N-(pyrid-2-ylmethylene)-phenylamines (ppa) in methanol to yield pentamethylcylopentadienyl ruthenium(II) Schiff base complexes of

  摘要[（η5-C5Me5）Ru（PPh3）2Cl]（1）在过量NH4PF6存在下与乙腈反应导致阳离子钌（II）络合物[（η5-C5Me5）Ru（PPh3）2 （CH3CN）] PF6（2）。配合物（2）与一系列N，N'供体席夫碱配体v 1反应。甲醇中的对位取代N-（吡啶-2-基亚甲基）-苯胺（ppa）得到五甲基环戊二烯基钌（II）席夫碱配合物[（η5-C5Me5）Ru（PPh3）（C5H4N-2-CH N- C6H4-pX）] PF6 [3a] PF6- [3f] PF6，其中C5Me5 =五甲基环戊二烯基，X = H，[3a] PF6，Me，[3b] PF6，OMe，[3c] PF6，NO2，[3d] PF6 ，Cl，[3e] PF6，COOH，[3f] PF6。分离出六氟磷酸盐的配合物。根据元素分析和NMR光谱对配合物进行了充分表征。代表性复合物的分子结构，
• Synthesis, characterization and magnetic properties of copper(II) complexes with 4-N-(2′-pyridylimine)benzoic acid
  作者：Chun-Fang Jiang、Fu-Pei Liang、Yan Li、Xiu-Jian Wang、Zi-Lu Chen、He-Dong Bian

  DOI：10.1016/j.molstruc.2006.12.020

  日期：2007.10

  Four Cu(II) complexes with 4-N-(2'-pyridylimine)benzoic acid (HL), [Cu(HL)(2)] center dot (ClO4)(2) (1), [Cu(HL)(2)(SO4)] center dot 3H(2)O (2), [Cu-2(L)(2)Cl-2](n) center dot 3H(2)O (3), and [Cu-4(L)(2)(HL)(2)Cl-4]center dot(CH3OH)(2)center dot(ClO4)(2) (4), have been synthesized and structurally characterized by X-ray crystallography. Complexes (1) and (2) both exhibit a mononuclear structure with a four-coordinated Cu(II) ion by the pyridineN and imine-N atoms of the ligands for (1) and a penta-coordinated Cu(II) ion by pyridine-N, imine-N atoms of the ligands and one oxygen atom of SO42- for (2). Complex (3) consists of a two-dimensional Cu(II) layer formed by deprotonated HL ligand linking four-membered Cu2Cl2 units. Complex (4) contains a tetranuclear Cu(II) coordination cation in which the Cu(II) ions are penta-coordinated in square pyramidal geometry by two bridging chloride atoms, two nitrogen atoms of HL ligand with undeprotonated carboxylic group, and one oxygen atom of syn,syn-carboxylato bridge. Magnetic susceptibility data show a weak ferromagnetic coupling between the Cu centers in (3) (J = 4.95 cm(-1)) and a weak antiferromagnetic interaction in (4) (J = -16.85 cm(-1)), respectively. (C) 2007 Elsevier B.V. All rights reserved.
• Palladium(II) and platinum(II) complexes containing hydrophilic pyridinylimine-based ligands
  作者：Brian P Buffin、Evan B Fonger、Abhijit Kundu

  DOI：10.1016/s0020-1693(03)00304-9

  日期：2003.11

  Reaction of the unsymmetrical hydrophilic pyridinylimine ligands 1a-e with either PdCl2(C6H5CN)(2) or PtCl2(C6H5CN)(2) affords the square-planar d(8) dichloride complexes 2a-e and 3, respectively. Formation of these divalent species effectively stabilizes the reactive imine bond towards hydrolysis. All of the Pd(II) and Pt(II) complexes were characterized by H-1 and C-13 NMR spectroscopy and elemental analysis. The solid-state structure of 2a was established by X-ray crystallography and reveals relatively little delocalization of the imine C=N bond upon metallacycle formation. (C) 2003 Elsevier Science B.V. All rights reserved.