N,N,N',N'-tetrakis(2-pyridyl)adipamide | 267664-33-5

• 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-pyridyl)adipamide
• 英文别名: tpada；N,N,N',N'-tetrapyridin-2-ylhexanediamide
• CAS: 267664-33-5
• 化学式: C₂₆H₂₄N₆O₂
• 分子量: 452.516
• InChiKey: DHHDJNYZMPIRNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  92.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (N-(hydroxyethyl)ethylenediaminetriacetato)ruthenate(II)(H2O)(1-) 、 N,N,N',N'-tetrakis(2-pyridyl)adipamide 以 not given 为溶剂， 生成 [Ru(hedta)]2(tpada)(2-)
  参考文献：
  名称：

  [RuII(hedta)]− complexes of 2,2′-dipyridylamine (dpaH) and a bifunctional tethered analog, N,N,N′,N′-tetrakis(2-pyridyl)adipamide (tpada)

  摘要：

  [Ru-II(hedta)L](-) complexes (hedta(3-) = N-hydroxyethylethylenediamine-N,N,N'-triacetate); L = dpaH (2, 2'-dipyridylamine) and tpada (N,N,N',N'-tetrakis(2-pyridyl)adipamide)) have been studied by H-1 NMR and electrochemical methods in aqueous solution. The bidentate rings of dpaH and tpada are differentiated as shown by NMR upon coordination to Ru-II due to differences in the local environment. The dpa-R headgroup of each ligand binds 'in-plane' with the en backbone of hedta(3-) and with one pyridyl ring being nearer the amine of hedta(3-) having the pendant glycinato group (matching the known arrangement with bpy (2,2'-bipyridine)). Ru-II/III E-1/2 values follow the order dpaH (0.32 V) < tpada (0.47 V) < bpy (0.54 V), showing that dpaH is a weaker pi-acceptor ligand than bpy, and that the withdrawing carbonyl functionality enhances the K-acceptor capacity for the tpada ligand, approaching the stability imparted by bpy. Only the 1:1 [Ru-II(hedta)(dpaH) complex forms even in the presence of excess dpaH. [Ru-II(hedta)(dpaH)] has a pK(a) of the dipyridylamine proton of approximately 5.0 with [Ru-III(hedta)(dpa(-))] undergoing aquation (k(H2O) = 1.4 x 10(-2) s(-1)) and OH--assisted dissociation (k(OH) = 1.33 x 10(4) M-1 s(-1)). The {[Ru-II-(hedta)](2)(tpada)}(2-) complex serves as a water-soluble model as to how {[ML'](2)(tpada)} complexes might act as an extended bridge betrveen two metal binding sites, potentially those of metalIo-derivatized DNA strands, or between one DNA strand and a protein crosslink. In this model M represents an appropriate metal for DNA derivatization such as Ru-II, Pt-II or Pd-II and L' represents the attachments to DNA nucleobase sites, aminocarboxylates/peptide coordination for antitumor purposes. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(99)00498-3
• 作为产物：
  描述：

  [Ru(hedta)]2(tpada)(2-) 以 水 为溶剂， 生成 [Ru(hedta)(OH)2](2-) 、 N,N,N',N'-tetrakis(2-pyridyl)adipamide
  参考文献：
  名称：

  [RuII(hedta)]− complexes of 2,2′-dipyridylamine (dpaH) and a bifunctional tethered analog, N,N,N′,N′-tetrakis(2-pyridyl)adipamide (tpada)

  摘要：

  [Ru-II(hedta)L](-) complexes (hedta(3-) = N-hydroxyethylethylenediamine-N,N,N'-triacetate); L = dpaH (2, 2'-dipyridylamine) and tpada (N,N,N',N'-tetrakis(2-pyridyl)adipamide)) have been studied by H-1 NMR and electrochemical methods in aqueous solution. The bidentate rings of dpaH and tpada are differentiated as shown by NMR upon coordination to Ru-II due to differences in the local environment. The dpa-R headgroup of each ligand binds 'in-plane' with the en backbone of hedta(3-) and with one pyridyl ring being nearer the amine of hedta(3-) having the pendant glycinato group (matching the known arrangement with bpy (2,2'-bipyridine)). Ru-II/III E-1/2 values follow the order dpaH (0.32 V) < tpada (0.47 V) < bpy (0.54 V), showing that dpaH is a weaker pi-acceptor ligand than bpy, and that the withdrawing carbonyl functionality enhances the K-acceptor capacity for the tpada ligand, approaching the stability imparted by bpy. Only the 1:1 [Ru-II(hedta)(dpaH) complex forms even in the presence of excess dpaH. [Ru-II(hedta)(dpaH)] has a pK(a) of the dipyridylamine proton of approximately 5.0 with [Ru-III(hedta)(dpa(-))] undergoing aquation (k(H2O) = 1.4 x 10(-2) s(-1)) and OH--assisted dissociation (k(OH) = 1.33 x 10(4) M-1 s(-1)). The {[Ru-II-(hedta)](2)(tpada)}(2-) complex serves as a water-soluble model as to how {[ML'](2)(tpada)} complexes might act as an extended bridge betrveen two metal binding sites, potentially those of metalIo-derivatized DNA strands, or between one DNA strand and a protein crosslink. In this model M represents an appropriate metal for DNA derivatization such as Ru-II, Pt-II or Pd-II and L' represents the attachments to DNA nucleobase sites, aminocarboxylates/peptide coordination for antitumor purposes. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(99)00498-3