2-((4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)methyl)pyridine-1-oxide | 819045-92-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-((4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)methyl)pyridine-1-oxide
• 英文别名: 10-[(1-oxidopyridin-2-yl)methyl]-1,4,7,10-retraazacyclododecane-1,4,7-triacetic acid；2-[4,7-Bis(carboxymethyl)-10-[(1-oxidopyridin-1-ium-2-yl)methyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid；2-[4,7-bis(carboxymethyl)-10-[(1-oxidopyridin-1-ium-2-yl)methyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
• CAS: 819045-92-6
• 化学式: C₂₀H₃₁N₅O₇
• 分子量: 453.495
• InChiKey: ILQGZGLLXDFUNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  氯化铥(III) 、 2-((4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl)methyl)pyridine-1-oxide 在 KOH 作用下， 以 水 为溶剂， 以75%的产率得到Tm(10-[(1-oxidopyridin-2-yl)methyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triacetate)]*3H2O
  参考文献：
  名称：

  Lanthanide(III) Complexes of Pyridine-N-Oxide Analogues of DOTA in Solution and in the Solid State. A New Kind of Isomerism in Complexes of DOTA-like Ligands

  摘要：

  The replacement of one of the acetate pendant arms with a 2-methylpyridine-N-oxide group in the molecule of H(4)dota significantly alters the coordination properties of the ligand in Ln(III) complexes. The structural properties of the complexes are investigated both in solution and in the solid state. The variable-temperature H-1 NMR spectra of Nd-III, Eu-III, and Yb-III complexes show that the twisted-square-antiprismatic (TSA) isomer is strongly destabilized and suppressed in solution and the complexes exist mostly as the square-antiprismatic (SA) isomers (98% for Eu-III at -35 degrees C). The exchange between the TSA and SA isomers is fast at room temperature compared to that of the NMR time scale. The flexibility of the six-membered chelate ring formed by coordination of the 2-methylpyridine-N-oxide group to the central ion allows two orientations of this pendant arm relative to the acetate arms: syn-SA (pyridine in the direction of the acetates) and anti-SA (pyridine opposite to the acetates). The syn-SA form was found in the X-ray structure of the Nd-III complex; the anti-SA forms were found in the structures of Dy-III, Tm-III, and Yb-III complexes. The UV-vis and H-1 NMR spectra of the Eu-III complex suggest that both forms are in dynamic equilibrium in solution. A derivatization of the pyridine-N-oxide group with a carboxylic group in the 4 position has no significant effect on the properties of the Ln(III) complexes.

  DOI：

  10.1021/ic801597z

文献信息

• COMPOUNDS FOR SEPARATION OF RARE EARTH ELEMENTS, METHOD OF SEPARATION, AND USE THEREOF
  申请人：Ustav organicke chemie a biochemie AV CR, v.v.i.

  公开号：EP3492460A1

  公开（公告）日：2019-06-05

  The present invention relates to the use of the compounds of general formula (I): wherein X, Y, Z, L, R and R1 are as described herein; for chromatographic separation of rare earth elements, as well as to the method of the separation of rare earth elements.

  本发明涉及通式（I）化合物的用途： 其中 X、Y、Z、L、R 和 R1 如本文所述； 以及分离稀土元素的方法。
• COMPOUNDS FOR SEPARATION OF RARE EARTH ELEMENTS AND S-, P-, D- METALS, METHOD OF SEPARATION, AND USE THEREOF
  申请人：Ustav Organicke Chemie a Biochemie AV CR, v.v.i.

  公开号：EP3717466A1

  公开（公告）日：2020-10-07
• Lanthanide(III) Complexes of Pyridine-<i>N</i>-Oxide Analogues of DOTA in Solution and in the Solid State. A New Kind of Isomerism in Complexes of DOTA-like Ligands
  作者：Miloslav Polášek、Jan Kotek、Petr Hermann、Ivana Císařová、Koen Binnemans、Ivan Lukeš

  DOI：10.1021/ic801597z

  日期：2009.1.19

  The replacement of one of the acetate pendant arms with a 2-methylpyridine-N-oxide group in the molecule of H(4)dota significantly alters the coordination properties of the ligand in Ln(III) complexes. The structural properties of the complexes are investigated both in solution and in the solid state. The variable-temperature H-1 NMR spectra of Nd-III, Eu-III, and Yb-III complexes show that the twisted-square-antiprismatic (TSA) isomer is strongly destabilized and suppressed in solution and the complexes exist mostly as the square-antiprismatic (SA) isomers (98% for Eu-III at -35 degrees C). The exchange between the TSA and SA isomers is fast at room temperature compared to that of the NMR time scale. The flexibility of the six-membered chelate ring formed by coordination of the 2-methylpyridine-N-oxide group to the central ion allows two orientations of this pendant arm relative to the acetate arms: syn-SA (pyridine in the direction of the acetates) and anti-SA (pyridine opposite to the acetates). The syn-SA form was found in the X-ray structure of the Nd-III complex; the anti-SA forms were found in the structures of Dy-III, Tm-III, and Yb-III complexes. The UV-vis and H-1 NMR spectra of the Eu-III complex suggest that both forms are in dynamic equilibrium in solution. A derivatization of the pyridine-N-oxide group with a carboxylic group in the 4 position has no significant effect on the properties of the Ln(III) complexes.