N,N'-bis[(6-methoxycarboxy-2-pyridyl)methyl]-4,13-diaza-18-crown-6 | 1127646-51-8

• 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'-bis[(6-methoxycarboxy-2-pyridyl)methyl]-4,13-diaza-18-crown-6
• 英文别名: Methyl 6-[[16-[(6-methoxycarbonylpyridin-2-yl)methyl]-1,4,10,13-tetraoxa-7,16-diazacyclooctadec-7-yl]methyl]pyridine-2-carboxylate
• CAS: 1127646-51-8
• 化学式: C₂₈H₄₀N₄O₈
• 分子量: 560.648
• InChiKey: VDSOTHIBUIYGIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N,N'-bis[(6-methoxycarboxy-2-pyridyl)methyl]-4,13-diaza-18-crown-6 在 盐酸 作用下， 以 水 为溶剂， 反应 40.0h， 以64%的产率得到N,N′-bis[(6-carboxy-2-pyridil)methyl]-4,13-diaza-18-crown-6 dihydrochloride
  参考文献：
  名称：

  Roca-Sabio, Adrian; Mato-Iglesias, Marta; Esteban-Gomez, David, Journal of the American Chemical Society, 2009, vol. 131, p. 3331 - 3341

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯甲基-2-吡啶羧酸甲酯 、 二氮杂18-冠醚-6 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 N,N'-bis[(6-methoxycarboxy-2-pyridyl)methyl]-4,13-diaza-18-crown-6
  参考文献：
  名称：

  Roca-Sabio, Adrian; Mato-Iglesias, Marta; Esteban-Gomez, David, Journal of the American Chemical Society, 2009, vol. 131, p. 3331 - 3341

  摘要：

  DOI：

文献信息

• Stabilizing Divalent Europium in Aqueous Solution Using Size-Discrimination and Electrostatic Effects
  作者：Martín Regueiro-Figueroa、José Luis Barriada、Agnès Pallier、David Esteban-Gómez、Andrés de Blas、Teresa Rodríguez-Blas、Éva Tóth、Carlos Platas-Iglesias

  DOI：10.1021/acs.inorgchem.5b00548

  日期：2015.5.18

  We report two macrocyclic ligands containing a 1,10-diaza-18-crown-6 fragment functionalized with either two picolinamide pendant arms (bpa18c6) or one picolinamide and one picolinate arm (ppa18c6(-)). The X-ray structure of [La(ppa18c6)(H2O)](2+) shows that the ligand binds to the metal ion using the six donor atoms of the crown moiety and the four donor atoms of the pendant arms, 11-coordination being completed by the presence of a coordinated water molecule. The X-ray structure of the [Sr(bpa18c6)(H2O)](2+) was also investigated due to the very similar ionic radii of Sr2+ and Eu2+. The structure of this complex is very similar to that of [La(ppa18c6)(H2O)](2+), with the metal ion being 11-coordinated. Potentiometric measurements were used to determine the stability constants of the complexes formed with La3+ and Eu3+. Both ligands present a very high selectivity for the large La3+ ion over the smaller Eu3+, with a size-discrimination ability that exceeds that of the analogous ligand containing two picolinate pendant arms reported previously (bp18c6(2-)). DFT calculations using the TPSSh functional and the large-core pseudopotential approximation provided stability trends in good agreement with the experimental values, indicating that charge neutral ligands derived from 1,10-diaza-18-crown-6 enhance the selectivity of the ligand for the large Ln(3+) ions. Cyclic voltammetry measurements show that the stabilization of Eu2+ by these ligands follows the sequence bp18c6(2-) < ppa18c6(-) < bpa18c6 with half-wave potentials of -753 mV (bp18c6(2-)), -610 mV (ppa18c6(-)), and -453 mV (bpa18c6) versus Ag/AgCl. These values reveal that the complex of bpa18c6 possesses higher stability against oxidation than the aquated ion, for which an E-1/2 value of -585 mV has been measured.