6,7,16,17-bisbenzo-9,14-diaza-1,5-dithia-cycloheptadeca-8,14-diene | 1044797-63-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6,7,16,17-bisbenzo-9,14-diaza-1,5-dithia-cycloheptadeca-8,14-diene
• CAS: 1044797-63-8
• 化学式: C₂₁H₂₄N₂S₂
• 分子量: 368.567
• InChiKey: OLADPIHBVZIZDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6,7,16,17-bisbenzo-9,14-diaza-1,5-dithia-cycloheptadeca-8,14-diene 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 6,7,16,17-bisbenzo-9,14-diaza-1,5-dithia-cycloheptadecane
  参考文献：
  名称：

  The structural and electrochemical consequences of hydrogenating copper N2S2 Schiff base macrocycles

  摘要：

  A series of cis and trans tetradentate copper macrocyclic complexes, of ring size 14-16, that employ amine and thioether donor groups are reported. Apart from 5,6,15,16-bisbenzo-8,13-diaza-1,4-dithiacyclohexadecane copper(I) (cis-[Cu(H4NbuSen)](+)) all of the complexes are obtained in the copper(II) form. Crystallographic analysis shows that the copper(II) complexes all adopt a distorted planar geometry around the copper. In contrast, cis-[Cu(H4NbuSen)](+) is found to adopt a distorted tetrahedral geometry. The complexes were subjected to electrochemical analysis in water and acetonitrile. The effect of the solvent, positions of the donor atoms (cis/trans) on E-1/2 is discussed as is the comparison of the electrochemical behaviour of these complexes with their parent Schiff base macrocycles. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.01.012
• 作为产物：
  描述：

  2,2'-bisbenzaldehyde 、 四亚甲基二胺 以 乙醇 为溶剂， 生成 6,7,16,17-bisbenzo-9,14-diaza-1,5-dithia-cycloheptadeca-8,14-diene
  参考文献：
  名称：

  The structural and electrochemical consequences of hydrogenating copper N2S2 Schiff base macrocycles

  摘要：

  A series of cis and trans tetradentate copper macrocyclic complexes, of ring size 14-16, that employ amine and thioether donor groups are reported. Apart from 5,6,15,16-bisbenzo-8,13-diaza-1,4-dithiacyclohexadecane copper(I) (cis-[Cu(H4NbuSen)](+)) all of the complexes are obtained in the copper(II) form. Crystallographic analysis shows that the copper(II) complexes all adopt a distorted planar geometry around the copper. In contrast, cis-[Cu(H4NbuSen)](+) is found to adopt a distorted tetrahedral geometry. The complexes were subjected to electrochemical analysis in water and acetonitrile. The effect of the solvent, positions of the donor atoms (cis/trans) on E-1/2 is discussed as is the comparison of the electrochemical behaviour of these complexes with their parent Schiff base macrocycles. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.01.012

文献信息

• Copper N2S2 Schiff base macrocycles: The effect of structure on redox potential
  作者：Michelle K. Taylor、Katherine D. Trotter、John Reglinski、Leonard E.A. Berlouis、Alan R. Kennedy、Corinne M. Spickett、Rebecca J. Sowden

  DOI：10.1016/j.ica.2008.02.021

  日期：2008.6

  A series of bis-salicylidene based N(2)S(2) copper macrocycles were prepared, structurally characterised and subjected to electrochemical analysis. The aim was to investigate the effects of length of polymethylene chains between either the imine donors or the sulfur donors on redox state and potential of the metal. The complexes structurally characterised had either distorted square planar or tetrahedral geometries depending on their oxidation state (Cu(2+) or Cu(+), respectively), and the N-(CH(2))(n)-N bridge was found to be most critical moiety in determining the redox potential and oxidation state of the copper macrocycles, with relatively little change in these properties caused by lengthening the S-(CH(2))(n)-S bridge from two to three carbons. In fact, a weakness was observed in the complexes at the sulfur donor, as further lengthening of the S-(CH(2))(n)-S methylene bridge to four carbons caused fission of the carbon-sulfur bond to give dimeric rings and supramolecular assemblies. Cu(+) complexes could be oxidised to Cu(2+) by tert-butylhydroperoxide, with a corresponding change in the spectrophotometric properties, and likewise Cu(2+) complexes could be reduced to Cu(+) by treatment with beta-mercaptoethylamine. However, repeated redox cycles appeared to compromise the stability of the macrocycles, most probably by a competing oxidation of the ligand. Thus the copper N(2)S(2) macrocycles show potential as redox sensors, but further development is required to improve their performance in a biochemical environment. (c) 2008 Elsevier B. V. All rights reserved.