N,N,N',N'-tetrakis(2-pyridylmethyl)benzene-1,4-diamine | 194924-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N,N',N'-tetrakis(2-pyridylmethyl)benzene-1,4-diamine
• 英文别名: 1,4-Benzenediamine, N,N,N',N'-tetrakis(2-pyridinylmethyl)-；1-N,1-N,4-N,4-N-tetrakis(pyridin-2-ylmethyl)benzene-1,4-diamine
• CAS: 194924-52-2
• 化学式: C₃₀H₂₈N₆
• 分子量: 472.593
• InChiKey: IZNRCEPQXXJXHM-UHFFFAOYSA-N

物化性质

• 熔点：
  196-197 °C (decomp)(Solv: methanol (67-56-1); hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  696.7±55.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N,N',N'-tetrakis(2-pyridylmethyl)benzene-1,4-diamine 在 iron(III) perchlorate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Buchen, Thomas; Hazell, Alan; Jessen, Lars, Journal of the Chemical Society, Dalton Transactions, 1997, p. 2697 - 2704

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯甲基吡啶盐酸盐 、 对苯二胺 在 sodium hydroxide 、 三乙胺 作用下， 以 水 、 苯 为溶剂， 反应 2.0h， 以48%的产率得到N,N,N',N'-tetrakis(2-pyridylmethyl)benzene-1,4-diamine
  参考文献：
  名称：

  Control of peroxyoxalate chemiluminescence by nitrogen-containing ligand quenching: turning off and on by ligand–metal ion host–guest interactions

  摘要：

  The control of peroxyoxalate chemiluminescence (PO-CL) by the coordination of nitrogen-containing ligands and metal cations was investigated. Turning the CL off and on was done by PO-CL using 15-monoazacrown-5-tethered anthracene and alkali metal ions. CL quenching and regeneration was also observed in the separated molecular system of 15-monoazacrown-5 and the fluorophores. CL quenching by a number of ligands bearing dipicolylamino groups was evaluated by these PO-CL reactions and found to be closely related to their oxidation potentials, which is dependent on the Weller rate law for electron exchange and this provides strong support for the existence of the CIEEL PO-CL process. When Zn2+ or Cu2+ are added to the PO-CL system quenched by the ligand, N-[2-(2,2'-dipicolylamino)ethyl]aniline, CL was turned on because the electron donating ability of the ligands was modulated. This was controlled by the coordination of the studied metal ions and, therefore, this system results in CL because of host-guest interactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.078

文献信息

• Aliphatic C–H Bond Halogenation by Iron(II)-α-Keto Acid Complexes and O₂: Functional Mimicking of Nonheme Iron Halogenases
  作者：Rahul Dev Jana、Debobrata Sheet、Sayanti Chatterjee、Tapan Kanti Paine

  DOI：10.1021/acs.inorgchem.8b00421

  日期：2018.8.6

  nonheme halogenases catalyze the halogenation of aliphatic C–H bonds in the biosynthesis pathway of many natural products. An iron(IV)-oxo-halo species has been established as the active oxidant in the halogenation reactions. With an objective to emulate the function of the nonheme halogenases, two iron(II)-α-keto acid complexes, [(phdpa)Fe(BF)Cl] (1) and [(1,4-tpbd)Fe2(BF)2Cl2] (2) (where phdpa = N

  α-酮戊二酸依赖性非血红素卤化酶催化许多天然产物生物合成途径中脂族C–H键的卤化。已经确定铁（IV）-氧-卤物质作为卤化反应中的活性氧化剂。为了模拟非血红素卤化酶的功能，两个铁（II）-α-酮酸络合物[[phdpa）Fe（BF）Cl]（1）和[（1,4-tpbd）Fe 2（BF ）2 Cl 2 ]（2）（其中phdpa = N，N-双（2-吡啶基甲基）苯胺，1,4-tpbd = N，N，N '，N'已经制备了-四（2-吡啶基甲基）苯-1,4-二胺，BF =苯甲酰甲酸酯。铁络合物能够使用O 2作为末端氧化剂对脂族C–H键进行氧化卤化。尽管复合物对CH键不具有卤化选择性，但它们是模仿非血红素卤化酶活性的非血红素铁（II）-α-酮酸复合物的唯一实例。双核复合物（2）对CH键的卤化/羟基化反应具有增强的反应性。
• Synthesis and Characterization of Some Dimeric Platinum Metal Complexes with N,N,N',N'-Tetrakis(2-pyridylmethyl)benzene-1,4-diamine
  作者：Surajit Chakrabarty、Shoumik Bhattacharjee、Afzal Hussain Sheikh、Aziz Ahmed、Subrata Pal、Prashanta Sarkhel

  DOI：10.14233/ajchem.2016.19437

  日期：——

  Dinuclear platinum metal complexes [M2(1,4-tpbd)Cl2]Cl2 (where, M = Pd or Pt and 1,4-tpbd = N,N,N,N-tetrakis(2-pyridylmethyl)benzene-1,4-diamine), [Ru2(1,4-tpbd)(DMSO)2Cl4] and [Rh2(1,4- tpbd)(PPh3)2Cl2] were synthesized from their precursors PdCl2, K2PtCl4, [Ru(DMSO)4Cl2] and [Rh(PPh3)3Cl2] respectively. The composition and the expected structures of the complexes have been discussed in view of their data obtained from various analytical, magnetic moment, molar conductance, UV-visible, FT-IR and 1H NMR spectroscopic studies. [M2(1,4-tpbd)Cl2]Cl2 (where, M = Pd or Pt) complexes were expected to have distorted square-planar geometries, in which the coordination of the ligand 1,4-tpbd to the metal ions occurs through all the N atoms in a bis-tridentate bridging fashion. The complex [Rh2(1,4-tpbd)(PPh3)2Cl2], a square-planar geometry was proposed, in which the ligand 1,4-tpbd bonded through two N-atoms of the picolyl group, one chlorine atom and one triphenylphosphine group per rhodium atom. An octahedral structure was proposed to the complex [Ru2(1,4-tpbd)(DMSO)2Cl4]. The electronic spectra of all the complexes were dominated by strong charge transfer bands indicative of binding of 1,4-tpbd ligand in a bridging manner to the metal centers. For the [Rh2(1,4-tpbd)(PPh3)2Cl2 complex in dichloromethane, a reversible peak at E½ = 0.39 V and DEp = 80 mV was observed, which may be assigned to two electrons RhI/RhIII oxidation couple.

  合二核铂金属配合物 [M2(1,4-tpbd)Cl2]Cl2（其中 M = Pd 或 Pt，1,4-tpbd = N,N,N,N-四(2-吡啶甲基)苯-1,4-二胺）、[Ru2(1,4-tpbd)(DMSO)2Cl4] 和 [Rh2(1,4-tpbd)(PPh3)2Cl2] 分别从其前驱物 PdCl2、K2PtCl4、[Ru(DMSO)4Cl2] 和 [Rh(PPh3)3Cl2] 合成。结合各种分析、磁矩、摩尔电导率、紫外-可见光、傅里叶变换红外及 ^1H NMR 光谱研究获得的数据，讨论了配合物的组成和预期结构。[M2(1,4-tpbd)Cl2]Cl2（其中 M = Pd 或 Pt）配合物预计具有扭曲的平面四方几何结构，其中配体 1,4-tpbd 通过所有氮原子以双三齿桥连方式与金属离子结合。对于配合物 [Rh2(1,4-tpbd)(PPh3)2Cl2]，提出其为平面四方几何结构，其中配体 1,4-tpbd 通过一个吡啶基的两个氮原子、一个氯原子和每个铑原子的一个三苯基磷基团进行配位。对于配合物 [Ru2(1,4-tpbd)(DMSO)2Cl4]，提出其为八面体结构。所有配合物的电子光谱都以强烈的电荷转移带为主，表明配体 1,4-tpbd 以桥连方式与金属中心结合。在二氯甲烷中的 [Rh2(1,4-tpbd)(PPh3)2Cl2] 配合物中观察到可逆峰，E½ = 0.39 V，DEp = 80 mV，这可能归因于两个电子的 RhI/RhIII 氧化偶。
• Syntheses, Structures, and Properties of Copper(II) Complexes of Bis(2-pyridylmethyl) Derivatives of <i>o</i>-, <i>m</i>-, and <i>p</i>-Phenylenediamine and Aniline
  作者：Sabrina Turba、Olaf Walter、Siegfried Schindler、Lars Preuss Nielsen、Alan Hazell、Christine J. McKenzie、Francesc Lloret、Joan Cano、Miguel Julve

  DOI：10.1021/ic800244g

  日期：2008.10.20

  Copper(II) complexes of the ligand 1,n-bis[bis(2-pyridylmethyl)amino]benzene with n = 2-4 (1,n-tpbd) and its mononuclear derivative bis(2-pyridylmethyl)aniline (phbpa) were synthesized and structurally characterized. Magnetic measurements and DFT calculations were performed on [CuCl2(phbpa)], [Cu2Cl4(1,3-tpbd)], [(Cu2Cl2(ClO4)(1,3-tpbd))Cl(Cu2Cl2(OH2)(1,3-tpbd))](ClO4)2, and [Cu2(OH2)2(S2O6)(1,3-tpbd)]S2O6

  配体1，n-双[双（2-吡啶基甲基）氨基]苯与n = 2-4（1，n-tpbd）的铜（II）配合物及其单核衍生物双（2-吡啶基甲基）苯胺（phbpa）合成并进行结构表征。对[CuCl2（phbpa）]，[Cu2Cl4（1,3-tpbd）]，[（Cu2Cl2（ClO4）（1,3-tpbd））Cl（Cu2Cl2（OH2）（1,3）进行磁测量和DFT计算-tpbd））]（ClO4）2和[Cu2（OH2）2（S2O6）（1,3-tpbd）] S2O6，成功地证明了交换极化机理。
• Synthesis, structure, and magnetic properties of a dinuclear antiferromagnetically coupled iron(II) complex
  作者：Fatima Setifi、Piotr Konieczny、Christopher Glidewell、Mina Arefian、Robert Pelka、Zouaoui Setifi、Masoud Mirzaei

  DOI：10.1016/j.molstruc.2017.07.085

  日期：2017.12

  Abstract A new dinuclear Fe(II) complex with the general formula [Fe 2 (1,4-tpbd)(dca) 4 (H 2 O) 2 ] ( 1 ) (in which 1,4-tpbd = N,N,N′,N′ -tetrakis(2-pyridylmethyl)benzene-1,4-diamine; dca = dicyanamide, [N(CN) 2 ] − ), has been prepared under hydrothermal conditions and fully characterized by elemental analysis, infrared spectroscopy, X-ray diffraction, and magnetic measurements. The compound crystallizes

  摘要 一种新的双核 Fe(II) 配合物，其通式为 [Fe 2 (1,4-tpbd)(dca) 4 (H 2 O) 2 ] ( 1 ) （其中 1,4-tpbd = N,N, N',N'-四(2-吡啶基甲基)苯-1,4-二胺；dca = 双氰胺，[N(CN) 2 ] - )，已在水热条件下制备，并通过元素分析、红外光谱、 X 射线衍射和磁测量。该化合物在三斜晶系和 P -1 空间群中结晶，Z = 1，晶胞参数如下：a = 8.165(5) A, b = 10.236(5) A, c = 13.105(5) A, α = 81.421(5)°, β = 78.810(5)°, γ = 72.941(5)°, V = 1022.2(9) A 3 。Fe(II) 离子是六配位的，以扭曲的八面体方式，由 tpbd 配体的三个 N 原子、一个水氧原子和两个双氰胺阴离子的两个 N 原子组成。通过桥接的
• Thermodynamic and kinetic study of the interaction between the Pt(<scp>ii</scp>) centres in [Pt₂(N,N,N′,N′-tetrakis(2-pyridylmethyl)diamine)(H₂O)₂]⁴⁺. Influence of the bridging ligand
  作者：Andreas Hofmann、Rudi van Eldik

  DOI：10.1039/b305174a

  日期：——

  higher reaction rates and a decrease in ΔH‡. In addition, the reactivity of one Pt(II) centre shows a clear dependence on the nature of the other Pt(II) centre, leading to different thermodynamic and kinetic properties for the first and second reaction steps. The interaction between the two Pt(II) centres mainly depends on the Pt–Pt distance and not on the aromatic or aliphatic nature of the bridging diamine

  合成了一系列双核Pt（II）配合物以研究四种不同桥联的影响二胺，即 苯-1,3-二胺， 苯-1,4-二胺， 1,3-丙二胺 和 1,4-丁二胺，与相应的单核相比，[Pt 2（N，N，N '，N'-四（2-吡啶基甲基）二胺）（H 2 O）2 ] 4+型配合物中铂中心的反应性络合物，[Pt（双（2-（吡啶基甲基）胺）（H 2 O）] 2+。在P ķ一确定两个去质子化步骤的值，并在拟一级反应条件下研究与氯化物反应的动力学，其为氯化物浓度和温度的函数。结果表明，双核配合物的亲电性高于单核配合物，这导致较低的p K a值，较高的反应速率和ΔH ‡的降低。此外，其中一个铂（反应性II）中心显示了其它的Pt（的性质明确的依赖性II）中心，从而导致所述第一和第二反应步骤不同的热力学和动力学性质。两种Pt（II）中心主要取决于Pt–Pt距离，而不取决于桥联二胺基团的芳族或脂族性质。在[Pt 2（N，N，N '，N'-四（2-吡啶基甲基）-1