[2'-(1,4,8,11-tetraazacyclotetradecan-1-yl)acetyl](tosyl)amide | 1313239-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2'-(1,4,8,11-tetraazacyclotetradecan-1-yl)acetyl](tosyl)amide
• 英文别名: N-(4-methylphenyl)sulfonyl-2-(1,4,8,11-tetrazacyclotetradec-1-yl)acetamide
• CAS: 1313239-26-7
• 化学式: C₁₉H₃₃N₅O₃S
• 分子量: 411.569
• InChiKey: VEEBVZRDYUAYFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,4,8,11-四氮杂环十四烷 、 2-bromo-N-[(4-methylphenyl)sulfonyl]acetylamide 在 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以50%的产率得到[2'-(1,4,8,11-tetraazacyclotetradecan-1-yl)acetyl](tosyl)amide
  参考文献：
  名称：

  Synthesis, structure and coordination properties of three cyclam-based ligands bearing one scorpionate arm

  摘要：

  In this work, three new cyclam-based ligands L-1, L-2 and L-3 bearing N-sulfonylacetamide pendant arm and their Cu(II), Zn(II), Cd(II) and Pb(II) complexes were synthesized and characterized by mass spectrometry, NMR, infrared and UV-Vis spectroscopies. The ligands present an original zwitterionic form in which the nitrogen atom of the sulfonylacetamide is deprotonated and one nitrogen of the macrocycle is protonated. This observation was confirmed by X-ray crystallography. The infrared spectra of the ligands revealed very low CO vibrational band values which can be explained by the fact that the oxygen atom is involved in some hydrogen bonds. The amidate form of the sulfonylacetamide arm is maintained upon complexation. Infrared data revealed a probable different coordination mode for Pb(II) than for the other three cations. Some additional studies by UV-Vis and EPR spectroscopies were performed for the Cu(II) complexes. Finally, the geometry coordination of the Cu(II) L-3, Zn(II) L-3 and Cd(II) L-3 complexes in the solid state was studied by X-ray crystallography. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.04.013

文献信息

• Synthesis, structure and coordination properties of three cyclam-based ligands bearing one scorpionate arm
  作者：Ramu Kannappan、Yoann Rousselin、Rim Zaari Jabri、Christine Goze、Stéphane Brandès、Roger Guilard、Abdellah Zrineh、Franck Denat

  DOI：10.1016/j.ica.2011.04.013

  日期：2011.7

  In this work, three new cyclam-based ligands L-1, L-2 and L-3 bearing N-sulfonylacetamide pendant arm and their Cu(II), Zn(II), Cd(II) and Pb(II) complexes were synthesized and characterized by mass spectrometry, NMR, infrared and UV-Vis spectroscopies. The ligands present an original zwitterionic form in which the nitrogen atom of the sulfonylacetamide is deprotonated and one nitrogen of the macrocycle is protonated. This observation was confirmed by X-ray crystallography. The infrared spectra of the ligands revealed very low CO vibrational band values which can be explained by the fact that the oxygen atom is involved in some hydrogen bonds. The amidate form of the sulfonylacetamide arm is maintained upon complexation. Infrared data revealed a probable different coordination mode for Pb(II) than for the other three cations. Some additional studies by UV-Vis and EPR spectroscopies were performed for the Cu(II) complexes. Finally, the geometry coordination of the Cu(II) L-3, Zn(II) L-3 and Cd(II) L-3 complexes in the solid state was studied by X-ray crystallography. (C) 2011 Elsevier B. V. All rights reserved.