N,N'-bis(benzimidazol-2-ylethyl)-1,2-ethanediamine | 125110-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N,N'-bis(benzimidazol-2-ylethyl)-1,2-ethanediamine
• 英文别名: N,N'-bis(benzimidazol-2-yl-ethyl)ethylenediamine；N,N'-bis(benzimidazole-2-ylethyl)ethylenediamine；N,N'-bis(benzimidazol-2-ylethyl)ethylenediamine；N,N'-bis(2-benzimidazolyethyl)ethylenediamine；N,N'-bis[2-(1H-benzimidazol-2-yl)ethyl]ethane-1,2-diamine
• CAS: 125110-84-1
• 化学式: C₂₀H₂₄N₆
• 分子量: 348.451
• InChiKey: YHHUCCUAEAOQSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.4
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tris(triphenylphosphine)ruthenium(II) chloride 、 N,N'-bis(benzimidazol-2-ylethyl)-1,2-ethanediamine 以 乙醇 为溶剂， 反应 0.33h， 以30%的产率得到
  参考文献：
  名称：

  Photochemical and antibacterial properties of ruthenium complex of N,N’-bis(benzimidazole-2yl-ethyl)ethylenediamine under visible light: Experimental and theoretical studies

  摘要：

  Complex [Ru(II)(LClP)-Cl-1(Ph-3)]Cl (L-1 = N,N'-bis(benzimidazol-2-yl ethyl)ethylenediamine) was prepared, and characterized completely by different analytical methods, and its photochemical behavior was studied under visible light. P-31 NMR results showed that a light assisted structural transformation in the complex occurred. The formation of different ruthenium complexes was also recorded by LC-MS: [Ru(II) L-1 DMSO)](2+) (m/z = 563, RT = 19.9 min); [Ru(II)(LDMSO)-D-1(H2O)](2+) (m/z = 581, RT = 15.69 min); [Ru(II)(LDMSO)-D-1(H2O) (MeOH)](2+) (m/z = 611, RT = 17.0 min); Ph2P(Cl) = O (m/z = 242, RT = 13.3 min). Theoretical study was used to interpret the structural change. The change of electron density rho(r) (dipole moment changes from 4.77 to 8.85 D) was observed in benzimidazole group in the excited state, altering the structural parameters of the complex. Furthermore, antibacterial study performed for the complex shows a high toxicity with bacterial cell even at low concentrations (50 mu L, 0.5 mM). This is consistent with low cell growth factor with [Ru(II)(LClP)-Cl-1(Ph-3)]Cl, established by Atomic Force Microscopy (AFM). (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.127377
• 作为产物：
  描述：

  3,3'-(1,2-乙二基二亚氨基)二丙酰胺 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 N,N'-bis(benzimidazol-2-ylethyl)-1,2-ethanediamine
  参考文献：
  名称：

  Sivagnanam, Usha; Pandiyan, Thangarasu; Palaniandavar, Mallayan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 5, p. 572 - 576

  摘要：

  DOI：

文献信息

• Synthesis, molecular structure and spectral analysis: DFT–TDDFT computational study of ruthenium complex of tetradentate N,N′-bis(benzimidazole-2yl-ethyl)-ethylenediamine
  作者：Hernández J. Guadalupe、Jayanthi Narayanan、Thangarasu Pandiyan

  DOI：10.1016/j.molstruc.2011.01.005

  日期：2011.3

  Abstract Ruthenium complex of N,N ′ - bis(benzimidazol-2-yl-ethyl)ethylenediamine (L 1 ) was prepared and characterized by analytical methods. Structural and spectral properties of N,N ′ - bis(benzimidazol-2-yl-ethyl)ethylenediamine (L 1 ), its dianionic structure (L 2 ), and their complexes such as [RuL 1 Cl(PPh 3 )] + and [RuL 2 Cl(PPh 3 )] + were studied by DFT. In the structures, the ruthenium ion is

  摘要 制备了N,N'-双(苯并咪唑-2-基-乙基)乙二胺(L 1 )的钌配合物，并用分析方法对其进行了表征。N,N ' - 双(苯并咪唑-2-基-乙基)乙二胺 (L 1 ) 的结构和光谱特性、其双阴离子结构 (L 2 ) 及其配合物如 [RuL 1 Cl(PPh 3 )] + 和[RuL 2 Cl(PPh 3 )] + 由DFT研究。在结构中，钌离子位于由胺、苯并咪唑氮以扭曲的八面体几何结构形成的赤道平面上，氯离子和三苯基膦轴向配位。此外，[Ru(L)Cl(PPh 3 )]Cl (L = L 1 或 L 2 ) 的分子轨道证明 HOMO 位于苯并咪唑和胺部分上，有利于与金属形成强键。DFT-TDDFT用于分析在可见光区观察到的MLCT带的分子轨道贡献；有趣的是，[RuL 1 Cl(PPh 3 )] + 的计算光谱仅与实验光谱的高能带（465 nm 和 350 nm）和其他可见光带（≈580
• Juen, Shi; Yishen, Zhang; Baoshen, Luo, Inorganica Chimica Acta, 1989, vol. 162, p. 29 - 32
  作者：Juen, Shi、Yishen, Zhang、Baoshen, Luo、Liaorong, Chen

  DOI：——

  日期：——
• Structure, spectra and redox behaviour of copper(II) complexes of bis(benzimidazolyl)diamine ligands
  作者：Thangarasu Pandiyan、Mallayan Palaniandavar、M. Lakshminarayanan、Hattikudur Manohar

  DOI：10.1039/dt9920003377

  日期：——

  The linear quadridentate ligand N,N'-bis(benzimidazol-2-ylethyl)ethane-1,2-diamine (L1) and its 1-methylbenzimidazole analogue (L2) and homologues form 1:1 complexes with Cu (ClO4)2; L1 also forms complexes of the types CuL1X2 where X = NO3, PF6, Br or Cl and CuL1(X)Y where X = Cl or Br and Y = ClO4 or Br. Deep blue CuL1Br2.2H2O crystallizes in the monoclinic space group C2/c with Z = 4, a = 9.919(2), b = 16.626(3), c = 14.102(3) angstrom and beta = 94.39(2)-degrees. The structure was solved by Patterson and Fourier difference methods and refined by the least-squares technique to R = 0.064 for 2195 independent reflections with / > 1.5sigma(/). The molecule lies on a two-fold axis symmetrically around Cu(II). The co-ordination around Cu(II) is found to be square planar with two amino nitrogens and two benzimidazole nitrogens forming the equatorial plane [Cu-N 1.983(3) and 2.037(4) angstrom]. The bromides are at longer distances [3.349(1) angstrom] in axial sites. Ligand field and EPR spectra indicate that one bromide or chloride ion is axially co-ordinated to Cu(II) in [CuL1]2+. This ion exhibits quasi-reversible redox behaviour. Electrochemical studies of the dihalides in methanol have established the presence of [CuL1X2], [CuL1(X)]+ and [CuL1]2+ in equilibrium. In complexes with 565 [CuL4]2+ [L4 = N,N'-bis(benzimidazol-2-ylmethyl)ethane-1,2-diamine] and 555 [CuL3]2+ [L3 = N,N'-bis(1-methylbenzimidazol-2-ylmethyl)propane-1,3-diamine] chelate rings, Cu(II) does not seem to lie in the N4 square plane, as revealed by their low A(parallel-to) values and irreversible electrochemical behaviour. The Cu(II)-Cu(I) redox potentials in methanol are in the order [CuL1]2+ < [CuL3]2+ < [CuL4]2+; this illustrates that six-membered chelate rings are suitable to stabilize Cu(II), when Cu-N sigma interactions are favourable.
• [N,N'-Bis(benzimidazol-2-ylethyl)-1,2-ethanediamine](nitrato-O,O')nickel(II) Nitrate
  作者：M. Soriano-García、T. Pandiyan、C. Durán de Bazúa

  DOI：10.1107/s010827019401406x

  日期：1995.6.15

  The structure of the title compound, [Ni(C20H24N6)(NO3)](NO3), consists of a distorted octahedral nickel complex with the central Ni atom coordinated to two N atoms of the benzimidazole moieties, two ethylenediamine N atoms and two O atoms of one of the nitrate ions; the other nitrate ion lies in a well defined position in the lattice and plays an important role in crystal packing. The dihedral angle between the two benzimidazole rings is 85.1(1)degrees. The crystal structure is stabilized by a three-dimensional network of N-H ... O and C-H ... O interactions, and N-H ... O intermolecular hydrogen bonds.