6-(((dipyridin-2-ylmethyl)((6-(phenylamino)pyridin-2-yl)methyl)amino)methyl)-N-phenylpyridin-2-ylamine | 1192188-16-1

• 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: 6-(((dipyridin-2-ylmethyl)((6-(phenylamino)pyridin-2-yl)methyl)amino)methyl)-N-phenylpyridin-2-ylamine
• 英文别名: 6-[[(6-anilinopyridin-2-yl)methyl-(dipyridin-2-ylmethyl)amino]methyl]-N-phenylpyridin-2-amine
• CAS: 1192188-16-1
• 化学式: C₃₅H₃₁N₇
• 分子量: 549.678
• InChiKey: JZASDQMMUJXZHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(((dipyridin-2-ylmethyl)((6-(phenylamino)pyridin-2-yl)methyl)amino)methyl)-N-phenylpyridin-2-ylamine 以 四氢呋喃 、 乙二醇二甲醚 、 重水 为溶剂， 生成 [Fe(III)(6-(((dipyridin-2-ylmethyl)((6-(phenylamino)pyridin-2-yl)methyl)amino)methyl)-N-phenylpyridin-2-ylamine)(OD)](OTf)2
  参考文献：
  名称：

  A Hydrogen-Bond Facilitated Cycle for Oxygen Reduction by an Acid- and Base-Compatible Iron Platform

  摘要：

  We report a hydrogen-bond functionalized N4Py ligand platform (N, N-bis(2-R-6-pyridylmethyl)-N-bis(2-pyridyl)methylamine; R = neopentyl-NH, N4py2(NpNH), g; R = phenyl-NH, N4Py(2PhNH), 10) and the ability of its iron(II)-triflate [(N4PyFeII)-Fe-2R(OTf)][OTf] complexes (R = NpNH, 11; R = PhNH, 12) to activate and reduce dioxygen in a synthetic cycle by coupled proton and electron transfer. A pair of iron(III)-hydroxide [N4Py(2R)Fe(III)(OH)][OTf](2) complexes (R = NpNH, 13; R = PhNH, 14) are isolated and structurally and spectroscopically characterized after exposure of the iron(II)-triflate precursors to 1 atm of O-2 at ambient temperature. The stability of this system to acids and bases allows regeneration of the labile iron(II)-triflate starting materials by sequential electron and proton transfer with cobaltocene and triflic acid, respectively, or through direct proton-coupled reduction with ascorbic acid. In the stepwise process, reduction of the iron(III)-hydroxide complexes with cobaltocene gives structurally homologous iron(II)-hydroxide [N4Py(2R)Fe(II)(OH)][OTf] congeners (R = NpNH, 15; R = PhNH, 16) that can be prepared independently from 11 and 12 with 20% aq. NaOH. Additions of triflic acid to complexes 15 and 16 furnish the starting compounds 11 and 12, respectively, to complete the synthetic cycle. The combined data establish a synthetic cycle for O-2 reduction by an iron platform that manages proton and electron transfer through its first and second coordination spheres.

  DOI：

  10.1021/ic9006668

文献信息

• A Hydrogen-Bond Facilitated Cycle for Oxygen Reduction by an Acid- and Base-Compatible Iron Platform
  作者：Han Sen Soo、Alexis C. Komor、Anthony T. Iavarone、Christopher J. Chang

  DOI：10.1021/ic9006668

  日期：2009.11.2

  We report a hydrogen-bond functionalized N4Py ligand platform (N, N-bis(2-R-6-pyridylmethyl)-N-bis(2-pyridyl)methylamine; R = neopentyl-NH, N4py2(NpNH), g; R = phenyl-NH, N4Py(2PhNH), 10) and the ability of its iron(II)-triflate [(N4PyFeII)-Fe-2R(OTf)][OTf] complexes (R = NpNH, 11; R = PhNH, 12) to activate and reduce dioxygen in a synthetic cycle by coupled proton and electron transfer. A pair of iron(III)-hydroxide [N4Py(2R)Fe(III)(OH)][OTf](2) complexes (R = NpNH, 13; R = PhNH, 14) are isolated and structurally and spectroscopically characterized after exposure of the iron(II)-triflate precursors to 1 atm of O-2 at ambient temperature. The stability of this system to acids and bases allows regeneration of the labile iron(II)-triflate starting materials by sequential electron and proton transfer with cobaltocene and triflic acid, respectively, or through direct proton-coupled reduction with ascorbic acid. In the stepwise process, reduction of the iron(III)-hydroxide complexes with cobaltocene gives structurally homologous iron(II)-hydroxide [N4Py(2R)Fe(II)(OH)][OTf] congeners (R = NpNH, 15; R = PhNH, 16) that can be prepared independently from 11 and 12 with 20% aq. NaOH. Additions of triflic acid to complexes 15 and 16 furnish the starting compounds 11 and 12, respectively, to complete the synthetic cycle. The combined data establish a synthetic cycle for O-2 reduction by an iron platform that manages proton and electron transfer through its first and second coordination spheres.