2,5-bis[1-(2,6-dimethylphenyl)iminoethyl]pyrazine | 280113-11-3

• 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: 2,5-bis[1-(2,6-dimethylphenyl)iminoethyl]pyrazine
• 英文别名: N-(2,6-dimethylphenyl)-1-[5-[N-(2,6-dimethylphenyl)-C-methylcarbonimidoyl]pyrazin-2-yl]ethanimine
• CAS: 280113-11-3
• 化学式: C₂₄H₂₆N₄
• 分子量: 370.497
• InChiKey: NDRZTBPXTKVYLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-(bromomesityl)bis(triphenylphosphino)nickel(II) 、 2,5-bis[1-(2,6-dimethylphenyl)iminoethyl]pyrazine 以 甲苯 为溶剂， 以93%的产率得到(Br(2,4,6-trimethylhenyl))2Ni(2,5-bis[1-(2,6-dimethylphenyl)iminoethyl]pyrazine)
  参考文献：
  名称：

  具有桥连双(芳基亚氨基)-1,4-吡嗪配体的双核芳基镍配合物

  摘要：

  [(μ-NN){Ni(Mes)Br}2] {NN = 2,5-双[1-(芳基)亚氨基乙基]吡嗪型的α-二亚胺螯合配体；Mes = mesityl = 2,4,6-trimethylphenyl} 已被制备并详细地电化学和光谱表征。核磁共振光谱和量子化学计算的组合允许分配立体异构体及其相对稳定性。可归因于电荷转移跃迁的长波长吸收（600-1000 nm）揭示了两个金属中心通过其低位 π* 轨道在配体桥上的显着电子耦合。可逆还原电化学产生稳定的自由基阴离子配合物，主要以配体为中心的自旋密度，如电子顺磁共振 (EPR) 光谱和游离配体及其镍配合物的紫外/可见光谱电化学结合 DFT 计算所示。在根岸交叉偶联反应中作为催化剂的配合物的初步研究给出了有希望的结果。

  DOI：

  10.1002/ejic.201101436

文献信息

• Electron Paramagnetic Resonance and Spectroscopic Characteristics of Electrogenerated Mixed-Valent Systems [(η⁵-C₅Me₅)M(μ-L)M(η⁵-C₅Me₅)]⁺ (M = Rh, Ir; L = 2,5-Diiminopyrazines) in Relation to the Radicals [(η⁵-C₅Me₅)ClM(μ-L)MCl(η⁵-C₅Me₅)]⁺ and [(η⁵-C₅Me₅)M(μ-L)MCl(η⁵-C₅Me₅)]²⁺
  作者：Sascha Berger、Axel Klein、Matthias Wanner、Wolfgang Kaim、Jan Fiedler

  DOI：10.1021/ic991110d

  日期：2000.6.1

  Electrochemical reduction of the dinuclear [(eta(5)-C5Me5)ClM(mu-L)MCl(eta(5)-C5Me5)(2+) ions (M = Rh, Ir; L = 2,5-bis(1-phenyliminoethyl)pyrazine (bpip) and 2,5-bis[1-(2,6-dimethylphenyl)iminoethyl]pyrazine (bxip)) proceeds via the paramagnetic intermediates [(eta(5)-C5Me5)ClM(mu-L)MCl(eta(5)-C5Me5)](+) (L = bpip) or [(eta(5)-C5Me5)M(mu-L)MCl(eta(5)-C5Me5)(2+) (L = bxip) and [(eta(5)-C5Me5)M(mu-L)M(eta(5)-C5Me5)](+). Whereas the first is clearly a radical species with a small g anisotropy, the chloride-free cations are distinguished by structured intervalence charge transfer (IVCT) bands in the near-infrared region and by rhombic electron paramagnetic resonance features between g 1.9 and g = 2.3, which suggests considerable metal participation at the singly occupied MO. Alternatives for the d configuration assignment and for the role of the bisbidentate-conjugated bridging ligands will be discussed. The main difference between bpip and bxip systems is the destabilization of the chloride-containing forms through the bxip ligand for reasons of steric interference.