Bis-N,N'-(2-methylquinoline)-1,2-trans-cyclohexanediimine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Bis-N,N'-(2-methylquinoline)-1,2-trans-cyclohexanediimine
• 英文别名: trans-1,2-cyclohexyl(N=CH-2-quinolyl)2
• 化学式: C₂₆H₂₄N₄
• 分子量: 392.503
• InChiKey: BIGOHQITWMVTQM-KRFMPFSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50.5
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bis[dimethyl(μ-dimethylsulfide)platinum(II)] 、 Bis-N,N'-(2-methylquinoline)-1,2-trans-cyclohexanediimine 以 乙醚 为溶剂， 以69%的产率得到R,R/S,S-trans-1,2-cyclohexyl[N=CH-2-quinolyl(PtMe2)]2
  参考文献：
  名称：

  Baar, Cliff R.; Carbray, Lee P.; Jennings, Michael C., Organometallics, 2000, vol. 19, # 13, p. 2482 - 2497

  摘要：

  DOI：
• 作为产物：
  描述：

  喹啉-2-甲醛 、 trans-1,2-Diaminocyclohexane 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以85%的产率得到Bis-N,N'-(2-methylquinoline)-1,2-trans-cyclohexanediimine
  参考文献：
  名称：

  Electrochemically Controlled Assembling/Disassembling Processes with a Bis-imine Bis-quinoline Ligand and the CuII/CuI Couple

  摘要：

  The bis-iminoquinoline quadridentate ligand L is capable of forming air- and moisture-stable complexes both with Cu-II and Cu-I; thus the L/Cu-II/I set is a bistable system. Owing to its quite rigid preorganized structure, L forms the 1:1 complex [(CuL)-L-II](2+) when binding the d(9) cation Cu2+, while with the d(10) cation Cu+, dimeric complexes of the [(Cu2L2)-L-I](2+) type are formed in which each copper cation is coordinated by two iminoquinoline fragments belonging to two different ligands. Crystal and molecular structure determinations showed that, in [(CuL)-L-II](CF3SO3)(2), L binds to the metal center in a square-planar fashion, while in [(Cu2L2)-L-I](CF3SO3)(2) the Cu+ cations are coordinated with a tetrahedral geometry, with the two ligands L intertwined in a double helix. On the other hand, in the case of [(Cu2L2)-L-I](ClO4)(2) both a helical species and a dimeric nonhelical one were found to coexist in the same crystal cell. However, spectrophotometric and H-1 NMR studies demonstrated that, in acetonitrile solution, only two helical forms exist, one of which is more prevalent (87%, at 20 degrees C). The interconversion equilibrium between the two helical forms has been studied in acetonitrile by temperature variable H-1 NMR and the pertinent Delta H-circle minus and Delta S-circle minus values have been determined; these account for the small difference in energy between the two species. Finally, cyclic voltammetry and spectroelectrochemical experiments demonstrated that in acetonitrile solution it is possible to rapidly transform [(CuL)-L-II](2+) into the helical [(Cu2L2)-L-I](2+) dimer (or vice versa) by changing the potential applied to the working electrode, that is, it is possible to electrochemically control the self-assembly/disassembly process through the Cu-II/Cu-I redox couple. Moreover, it has been shown that self-assembly (reduction)/disassembly (oxidation) cycles can be repeated at will, without any degradation of the system.

  DOI：

  10.1002/(sici)1521-3765(19991203)5:12<3679::aid-chem3679>3.0.co;2-j

文献信息

• Chiral palladium(II) complexes bearing tetradentate nitrogen ligands: synthesis, crystal structure and reactivity towards the polymerization of norbornene
  作者：Adnan S. Abu-Surrah、Ulf Thewalt、Bernhard Rieger

  DOI：10.1016/s0022-328x(99)00273-9

  日期：1999.9

  palladium(II) complexes of the types [(1,2,4)PdCl2] (5a, 6a, 7) and [(1,2,3,4)Pd(NCCH3)x](Y)2 (5b, 5c, 6b, 6c, 8, 9), x=0, 2; Y=BF4 −, NO3 − is reported. The dicationic palladium(II) complex [Pd(DBQED)(NO3)2·H2O] (5c) crystallizes in the monoclinic space groups P21/c (no. 14) with a=11.458(1), b=15.302(1) Å, c=20.644(2) Å, β=99.23(1)° and V=3572.7 Å3, Z=4. All four nitrogen donors are attached to the Pd(II)-center

  一系列四足氮配体的合成（N，N'-二苄基-N，N'-二（喹啉-2-甲基）-1,2-乙二胺（DBQED，1），N，N'-二甲基- N，N'-二（喹啉-2-甲基）-1,2-乙二胺（DMQED，2），（1 R，2 R）-（-）- N， N'-di （喹啉-2-亚甲基）二亚氨基环己烷（DQEDC，3），N，N'-二（喹啉-2-亚甲基）-1,2-亚苯基二亚胺（DQPD，4）及其相应的中性和阳离子钯（II）配合物类型[ 1，2，4）的PdCl 2]（图5a，图6a，7）和[（1，2，3，4）的Pd（NCCH 3）X ]（Y）2（图5b，图5c，图6b，图6c，8，9），X = 0，2; Y = BF 4 -，NO 3 -被报告。钯（II）络合物[Pd（DBQED）（NO 3）2 ·H 2 O]（5c）在单斜空间群中结晶P 2 1 / ç（14号）与一个= 11.458（1），b = 15.302（1）埃，c
• An Enantiomerically Pure Schiff Base Ligand
  作者：A. S. Abu-Surrah、T. V. Laine、T. Repo、R. Fawzi、M. Steimann、B. Rieger

  DOI：10.1107/s0108270197006148

  日期：1997.10.15

  (1R,2R)-(-)-N, N'-Bis(quinoline-2-methylidene)-1,2-cyclohexanediamine, C26H24N4, was prepared by the reaction of quinoline-2-carbaldehyde and the corresponding diamine. The crystal structure of the resulting enantiomerically pure quadridentate ligand has been determined.

  (1R,2R)-(-)-N,N'-双(2-喹啉甲基亚胺)-1,2-环己二胺，C26H24N4，是通过2-喹啉甲醛与相应的二胺反应制备的。所得对映体纯的四齿配体的晶体结构已确定。
• Electrochemically Controlled Assembling/Disassembling Processes with a Bis-imine Bis-quinoline Ligand and the CuII/CuI Couple
  作者：Valeria Amendola、Luigi Fabbrizzi、Laura Linati、Carlo Mangano、Piersandro Pallavicini、Valentina Pedrazzini、Michele Zema

  DOI：10.1002/(sici)1521-3765(19991203)5:12<3679::aid-chem3679>3.0.co;2-j

  日期：1999.12.3

  The bis-iminoquinoline quadridentate ligand L is capable of forming air- and moisture-stable complexes both with Cu-II and Cu-I; thus the L/Cu-II/I set is a bistable system. Owing to its quite rigid preorganized structure, L forms the 1:1 complex [(CuL)-L-II](2+) when binding the d(9) cation Cu2+, while with the d(10) cation Cu+, dimeric complexes of the [(Cu2L2)-L-I](2+) type are formed in which each copper cation is coordinated by two iminoquinoline fragments belonging to two different ligands. Crystal and molecular structure determinations showed that, in [(CuL)-L-II](CF3SO3)(2), L binds to the metal center in a square-planar fashion, while in [(Cu2L2)-L-I](CF3SO3)(2) the Cu+ cations are coordinated with a tetrahedral geometry, with the two ligands L intertwined in a double helix. On the other hand, in the case of [(Cu2L2)-L-I](ClO4)(2) both a helical species and a dimeric nonhelical one were found to coexist in the same crystal cell. However, spectrophotometric and H-1 NMR studies demonstrated that, in acetonitrile solution, only two helical forms exist, one of which is more prevalent (87%, at 20 degrees C). The interconversion equilibrium between the two helical forms has been studied in acetonitrile by temperature variable H-1 NMR and the pertinent Delta H-circle minus and Delta S-circle minus values have been determined; these account for the small difference in energy between the two species. Finally, cyclic voltammetry and spectroelectrochemical experiments demonstrated that in acetonitrile solution it is possible to rapidly transform [(CuL)-L-II](2+) into the helical [(Cu2L2)-L-I](2+) dimer (or vice versa) by changing the potential applied to the working electrode, that is, it is possible to electrochemically control the self-assembly/disassembly process through the Cu-II/Cu-I redox couple. Moreover, it has been shown that self-assembly (reduction)/disassembly (oxidation) cycles can be repeated at will, without any degradation of the system.
• Baar, Cliff R.; Carbray, Lee P.; Jennings, Michael C., Organometallics, <hi>2000</hi>, vol. 19, # 13, p. 2482 - 2497
  作者：Baar, Cliff R.、Carbray, Lee P.、Jennings, Michael C.、Puddephatt, Richard J.

  DOI：——

  日期：——