N,N'-diethyl-N,N'-ditolyl-2,9-diamide-1,10-phenanthroline | 1533454-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: N,N'-diethyl-N,N'-ditolyl-2,9-diamide-1,10-phenanthroline
• 英文别名: N,N’-diethyl-N,N’-ditolyl-2,9-dicarboxamide-1,10-phenanthroline；N²,N⁹-diethyl-N²,N⁹-di-p-tolyl-1,10-phenanthroline-2,9-dicarboxamide；N,N'-diethyl-N,N'-di(p-tolyl)-1,10-phenanthroline-2,9-dicarboxamide；2-N,9-N-diethyl-2-N,9-N-bis(4-methylphenyl)-1,10-phenanthroline-2,9-dicarboxamide
• CAS: 1533454-15-7
• 化学式: C₃₂H₃₀N₄O₂
• 分子量: 502.616
• InChiKey: FSGXOTSTBMUIOR-UHFFFAOYSA-N

物化性质

• 沸点：
  731.6±60.0 °C(predicted)
• 密度：
  1.242±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  thorium(IV) nitrate pentahydrate 、 N,N'-diethyl-N,N'-ditolyl-2,9-diamide-1,10-phenanthroline 以 水 、 丙酮 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Excellent Selectivity for Actinides with a Tetradentate 2,9-Diamide-1,10-Phenanthroline Ligand in Highly Acidic Solution: A Hard–Soft Donor Combined Strategy

  摘要：

  In this work, we reported a phenanthroline-based tetradentate ligand with hard-soft donors combined in the same molecule, N,N'-diethyl-N,N'-ditolyl-2,9-diamide-1,10-phenanthroline (Et-Tol-DAPhen), for the group separation of actinides over lanthanides. The synthesis and solvent extraction as well as complexation behaviors of the ligand with actinides and lanthanides are studied experimentally and theoretically. The ligand exhibits excellent extraction ability and high selectivity toward hexavalent, tetravalent, and trivalent actinides over lanthanides in highly acidic solution. The chemical stoichiometry of Th(IV) and U(VI) complexes with Et-Tol-DAPhen is determined to be 1:1 using X-ray crystallography. The stability constants of some typical actinide and lanthanide complexes of Et-Tol-DAPhen are also determined in methanol by UV-vis spectrometry. Density functional theory (DFT) calculations reveal that the An-N bonds of the Et-Tol-DAPhen complexes have more covalent characters than the corresponding Eu-N bonds, which may in turn lead to the selectivity of Et-Tol-DAPhen toward actinides. This ligand possesses merits of both alkylamide and 219-bis-(5,6-dialkyl-1,2,4-triazin-3-yl)-1,10-phenanthroline (R-BTPhen) extractants for efficient actinide extraction and the selectivity toward minor actinides over lanthanides and hence renders huge potential opportunities in high-level liquid waste (HLLW) partitioning.

  DOI：

  10.1021/ic402784c
• 作为产物：
  描述：

  1,10-菲啰啉-2,9-二甲醛 在 氯化亚砜 、 硝酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 N,N'-diethyl-N,N'-ditolyl-2,9-diamide-1,10-phenanthroline
  参考文献：
  名称：

  Excellent Selectivity for Actinides with a Tetradentate 2,9-Diamide-1,10-Phenanthroline Ligand in Highly Acidic Solution: A Hard–Soft Donor Combined Strategy

  摘要：

  In this work, we reported a phenanthroline-based tetradentate ligand with hard-soft donors combined in the same molecule, N,N'-diethyl-N,N'-ditolyl-2,9-diamide-1,10-phenanthroline (Et-Tol-DAPhen), for the group separation of actinides over lanthanides. The synthesis and solvent extraction as well as complexation behaviors of the ligand with actinides and lanthanides are studied experimentally and theoretically. The ligand exhibits excellent extraction ability and high selectivity toward hexavalent, tetravalent, and trivalent actinides over lanthanides in highly acidic solution. The chemical stoichiometry of Th(IV) and U(VI) complexes with Et-Tol-DAPhen is determined to be 1:1 using X-ray crystallography. The stability constants of some typical actinide and lanthanide complexes of Et-Tol-DAPhen are also determined in methanol by UV-vis spectrometry. Density functional theory (DFT) calculations reveal that the An-N bonds of the Et-Tol-DAPhen complexes have more covalent characters than the corresponding Eu-N bonds, which may in turn lead to the selectivity of Et-Tol-DAPhen toward actinides. This ligand possesses merits of both alkylamide and 219-bis-(5,6-dialkyl-1,2,4-triazin-3-yl)-1,10-phenanthroline (R-BTPhen) extractants for efficient actinide extraction and the selectivity toward minor actinides over lanthanides and hence renders huge potential opportunities in high-level liquid waste (HLLW) partitioning.

  DOI：

  10.1021/ic402784c

文献信息

• High selectivity towards small copper ions by a preorganized phenanthroline-derived tetradentate ligand and new insight into the complexation mechanism
  作者：Cheng-Liang Xiao、Qun-Yan Wu、Lei Mei、Li-Yong Yuan、Cong-Zhi Wang、Yu-Liang Zhao、Zhi-Fang Chai、Wei-Qun Shi

  DOI：10.1039/c4dt01489h

  日期：——

  A preorganized tetradentate phenanthroline-derived amide ligand was found to show high selectivity towards small copper ions.

  一种预先组织的四齿菲咯啉衍生酰胺配体被发现对小型铜离子表现出高选择性。
• 1,10-Phenanthroline-2,9-dicarboxylic acid diamides: synthesis, structure, and solubility
  作者：V. S. Petrov、N. A. Avagyan、P. S. Lamport、P. I. Matveev、M. V. Evsiunina、V. A. Roznyatovsky、B. N. Tarasevich、K. L. Isakovskaya、Yu. A. Ustynyuk、V. G. Nenajdenko

  DOI：10.1007/s11172-023-3834-7

  日期：2023.3

  wide range of 1,10-phenanthroline-2,9-dicarboxylic acid diamides was synthesized, differing in the structure of substituents in the amide function and in the nature of substituents at positions 4 and 7 of the heteroaromatic ring. All new compounds were characterized by NMR, IR spectroscopy, and high resolution mass spectrometry. The molecular structure of one of the ligands was unambiguously confirmed

  合成了多种 1,10-phenanthroline-2,9-dicarboxylic acid acid diamides，它们在酰胺功能中的取代基结构以及杂芳环 4 和 7 位取代基的性质不同。所有新化合物均通过核磁共振、红外光谱和高分辨率质谱进行了表征。其中一种配体的分子结构已通过 X 射线衍射分析得到明确证实。定量评价所有获得的化合物在3-硝基三氟甲苯中的溶解度。
• Excellent Selectivity for Actinides with a Tetradentate 2,9-Diamide-1,10-Phenanthroline Ligand in Highly Acidic Solution: A Hard–Soft Donor Combined Strategy
  作者：Cheng-Liang Xiao、Cong-Zhi Wang、Li-Yong Yuan、Bin Li、Hui He、Shuao Wang、Yu-Liang Zhao、Zhi-Fang Chai、Wei-Qun Shi

  DOI：10.1021/ic402784c

  日期：2014.2.3

  In this work, we reported a phenanthroline-based tetradentate ligand with hard-soft donors combined in the same molecule, N,N'-diethyl-N,N'-ditolyl-2,9-diamide-1,10-phenanthroline (Et-Tol-DAPhen), for the group separation of actinides over lanthanides. The synthesis and solvent extraction as well as complexation behaviors of the ligand with actinides and lanthanides are studied experimentally and theoretically. The ligand exhibits excellent extraction ability and high selectivity toward hexavalent, tetravalent, and trivalent actinides over lanthanides in highly acidic solution. The chemical stoichiometry of Th(IV) and U(VI) complexes with Et-Tol-DAPhen is determined to be 1:1 using X-ray crystallography. The stability constants of some typical actinide and lanthanide complexes of Et-Tol-DAPhen are also determined in methanol by UV-vis spectrometry. Density functional theory (DFT) calculations reveal that the An-N bonds of the Et-Tol-DAPhen complexes have more covalent characters than the corresponding Eu-N bonds, which may in turn lead to the selectivity of Et-Tol-DAPhen toward actinides. This ligand possesses merits of both alkylamide and 219-bis-(5,6-dialkyl-1,2,4-triazin-3-yl)-1,10-phenanthroline (R-BTPhen) extractants for efficient actinide extraction and the selectivity toward minor actinides over lanthanides and hence renders huge potential opportunities in high-level liquid waste (HLLW) partitioning.