bis(1-methyl-2-imidazolyl)glyoxal | 20062-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(1-methyl-2-imidazolyl)glyoxal
• 英文别名: 2,2'-Oxalyl-bis-(1-methylimidazol)；Bis-<1-methyl-imidazolyl-(2)>-glyoxal；bis(1-methylimidazol-2-yl)glyoxal；bis-(1-methyl-1H-imidazol-2-yl)-ethanedione；big；1,2-Bis(1-methylimidazol-2-yl)ethane-1,2-dione；1,2-bis(1-methylimidazol-2-yl)ethane-1,2-dione
• CAS: 20062-59-3
• 化学式: C₁₀H₁₀N₄O₂
• 分子量: 218.215
• InChiKey: QXRBOPZFXNSRJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(1-methyl-2-imidazolyl)glyoxal 、 五羰基氯铼(I) 以 甲苯 为溶剂， 以70%的产率得到(μ-bis(1-methyl-2-imidazolyl)glyoxal)[fac-Re(carbonyl)3Cl]2
  参考文献：
  名称：

  Knoedler, Axel; Wanner, Matthias; Fiedler, Jan, Journal of the Chemical Society, Dalton Transactions, 2002, # 15, p. 3079 - 3084

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基咪唑 、 草酰氯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 bis(1-methyl-2-imidazolyl)glyoxal
  参考文献：
  名称：

  Organoosmium complexes of imidazole-containing chelate acceptor ligands

  摘要：

  The complexes [(L)Os(eta(6)-Cym)Cl](PF6), Cym = p-cymene and L = bis(1-methylimidazol-2-yl) ketone (bik) or bis(1-methylimidazol-2-yl) glyoxal (big), were obtained and characterized with respect to spectroscopy, crystal structure (big complex) and (spectro)electrochemical behaviour at variable temperatures. DFT calculations confirm the structure of [(big)Os(eta(6)-Cym)Cl](+) with imidazolyl-N-bonded Os-II in a boat-shaped seven-membered chelate ring with small N-Os-N angles (<84 degrees). Reduction of this compound proceeds reversibly to a neutral complex of the alpha-semidione radical anion ligand big; EPR and IR spectroelectrochemistry indicate very little participation from the heavy metal in the spin distribution. The analogous [(bik)Os(eta(6)-Cym)Cl](+) could not be reduced reversibly to the ketyl radical complex but displayed a more reversible oxidation at high potential. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.04.007

文献信息

• Reversibly Reducible <i>cis</i>-Dichloroplatinum(II) and <i>cis</i>-Dichloropalladium(II) Complexes of Bis(1-methylimidazol-2-yl)glyoxal
  作者：Ece Bulak、Markus Leboschka、Brigitte Schwederski、Orkan Sarper、Tereza Varnali、Jan Fiedler、Falk Lissner、Thomas Schleid、Wolfgang Kaim

  DOI：10.1021/ic070185b

  日期：2007.7.1

  observed for the platinum compound. Both the PdII and PtII complexes undergo reversible one-electron reduction in CH2Cl2/ 0.1 M Bu4NPF6; the reduced palladium compound disintegrates above -30 degrees C. Electron paramagnetic resonance (EPR), UV-vis, and IR spectroelectrochemistry studies were employed to study the monoanions. The anion radical complex [cis-PtCl2(big)]*- exhibits a well-resolved EPR spectrum

  制备了顺式-MCl 2（big），大＝双（1-甲基咪唑-2-基）乙二醛，M ＝ Pt，Pd的配合物，并通过电化学，光谱法进行了表征，对于M ＝ Pt，通过X射线结构分析对其进行了表征。通过配体的N，N'配位形成的七元螯​​合环大都显示出舟状构象，与密度泛函理论（DFT）计算结果相符。对于铂化合物没有观察到明显的分子间相互作用。PdII和PtII配合物在CH2Cl2 / 0.1 M Bu4NPF6中均经历可逆的单电子还原；还原的钯化合物在-30摄氏度以上会崩解。采用电子顺磁共振（EPR），UV-vis和IR光谱电化学研究来研究单阴离子。阴离子自由基络合物[顺式-PtCl2（大）] *-表现出良好的EPR光谱，具有小的但可检测的g各向异性和12.2 G的各向同性195Pt超精细偶合。DFT计算证实了α-半二酮中的自旋浓度自由基络合物的一部分，具有较小的离域到双（咪唑基）金属部分。结果表明，EP
• Koordination von Rhodium(III), Iridium(III) und Kupfer(II) mit dem potentiell vierzähnigen Akzeptorliganden Bis(1-methylimidazol-2-yl)glyoxal (big)
  作者：Markus Albrecht、Wolfgang Kaim

  DOI：10.1002/(sici)1521-3749(200006)626:6<1341::aid-zaac1341>3.0.co;2-0

  日期：2000.6

  Bis(1-methylimidazol-2-yl)glyoxal (big) which has hitherto not been used in coordination chemistry crystallizes to form Two perpendicular 1-methylimidazol-2-yl-carbonyl molecular halves. Out of the various possibilities for mono- and bis-chelate coordination the N,N'-alternative with a seven-membered chelate ring is realized in [Cp*Cl(big)Rh](PF6) as evident from crystal structure analysis. The iridium analogue reacts under hydration of big and elimination of HCl to form a complex cation [Cp*(bigOH)Ir](+) which dimerizes in the crystal through hydrogen bonding and contains one five- and one six-membered chelate ring involving the alcoholate-O. Cu(ClO4)(2) and the ligand big yield a complex ion [Cu(big)(2)](2+) with an ESR spectrum that suggests the coordination of the central metal by four N atoms in an approximately planar setting.