N,N'-bis(3-bromophenyl)-N,N'-bis(2-methoxyphenyl)benzene-1,3-diamine | 953413-34-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis(3-bromophenyl)-N,N'-bis(2-methoxyphenyl)benzene-1,3-diamine
• 英文别名: 1-N,3-N-bis(3-bromophenyl)-1-N,3-N-bis(2-methoxyphenyl)benzene-1,3-diamine
• CAS: 953413-34-8
• 化学式: C₃₂H₂₆Br₂N₂O₂
• 分子量: 630.379
• InChiKey: MBSHGCOOTOMTAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3-bromophenyl)-N,N'-bis(2-methoxyphenyl)benzene-1,3-diamine 、 邻甲氧基苯胺 在 palladium diacetate 二苯基膦基二茂铁 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以90%的产率得到N,N'-bis[3-(2-methoxyanilino)phenyl]-N,N'-bis(2-methoxyphenyl)benzene-1,3-diamine
  参考文献：
  名称：

  Disjoint and coextensive amminium radical cations: a general problem in making amminium radical cation based high-spin polymers

  摘要：

  A two-electron oxidation of N,N,N',N'-tetrakis(2-methoxyphenyl)-1,3-diaminobenzene 12 gives the diradical dication 12(2.+), which is an aza analogue of the Schlenk hydrocarbon and, like the Schlenk hydrocarbon, has a triplet ground state. However, an attempt to produce pentuplet tetraradical tetracations by extending the same ferromagnetic spin-coupling motif in a linear or a cyclic fashion was unsuccessful. Two-electron oxidations to give disjoint diradical dications (in which the charges and spins are spatially separated) are relatively easy but it proved impossible to remove the third and fourth electrons. This would require generation of coextensive radical ions in which the charges and spin distributions overlap. The results obtained with these model oligomers illustrate what is a general problem in the creation of high-spin polymers in which the spin-bearing centres are amminium radical cations. Strong ferromagnetic spin-coupling depends on the formation of coextensive rather than disjoint radical cations but the formation of coextensive radical cations with strong ferromagnetic coupling involves a large additional coulombic penalty. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.038
• 作为产物：
  描述：

  N,N'-bis(2-methoxyphenyl)benzene-1,3-diamine 、 1,3-二溴苯 在 palladium diacetate 二苯基膦基二茂铁 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到N,N'-bis(3-bromophenyl)-N,N'-bis(2-methoxyphenyl)benzene-1,3-diamine
  参考文献：
  名称：

  Disjoint and coextensive amminium radical cations: a general problem in making amminium radical cation based high-spin polymers

  摘要：

  A two-electron oxidation of N,N,N',N'-tetrakis(2-methoxyphenyl)-1,3-diaminobenzene 12 gives the diradical dication 12(2.+), which is an aza analogue of the Schlenk hydrocarbon and, like the Schlenk hydrocarbon, has a triplet ground state. However, an attempt to produce pentuplet tetraradical tetracations by extending the same ferromagnetic spin-coupling motif in a linear or a cyclic fashion was unsuccessful. Two-electron oxidations to give disjoint diradical dications (in which the charges and spins are spatially separated) are relatively easy but it proved impossible to remove the third and fourth electrons. This would require generation of coextensive radical ions in which the charges and spin distributions overlap. The results obtained with these model oligomers illustrate what is a general problem in the creation of high-spin polymers in which the spin-bearing centres are amminium radical cations. Strong ferromagnetic spin-coupling depends on the formation of coextensive rather than disjoint radical cations but the formation of coextensive radical cations with strong ferromagnetic coupling involves a large additional coulombic penalty. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.038

文献信息

• Disjoint and coextensive amminium radical cations: a general problem in making amminium radical cation based high-spin polymers
  作者：Richard J. Bushby、Colin A. Kilner、Norman Taylor、Matthew E. Vale

  DOI：10.1016/j.tet.2007.08.038

  日期：2007.11

  A two-electron oxidation of N,N,N',N'-tetrakis(2-methoxyphenyl)-1,3-diaminobenzene 12 gives the diradical dication 12(2.+), which is an aza analogue of the Schlenk hydrocarbon and, like the Schlenk hydrocarbon, has a triplet ground state. However, an attempt to produce pentuplet tetraradical tetracations by extending the same ferromagnetic spin-coupling motif in a linear or a cyclic fashion was unsuccessful. Two-electron oxidations to give disjoint diradical dications (in which the charges and spins are spatially separated) are relatively easy but it proved impossible to remove the third and fourth electrons. This would require generation of coextensive radical ions in which the charges and spin distributions overlap. The results obtained with these model oligomers illustrate what is a general problem in the creation of high-spin polymers in which the spin-bearing centres are amminium radical cations. Strong ferromagnetic spin-coupling depends on the formation of coextensive rather than disjoint radical cations but the formation of coextensive radical cations with strong ferromagnetic coupling involves a large additional coulombic penalty. (C) 2007 Elsevier Ltd. All rights reserved.