1-acetamido-3-methylbenzimidazolium bromide | 1165949-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-acetamido-3-methylbenzimidazolium bromide
• 英文别名: 3-(carbamoylmethyl)-1-methylbenzimidazolium bromide；1-methylacetamido-3-methylbenzimidazolium bromide；[CH3-Bim-CH2CONH2]Br；2-(3-methylbenzimidazol-3-ium-1-yl)acetamide;bromide
• CAS: 1165949-70-1
• 化学式: Br*C₁₀H₁₂N₃O
• 分子量: 270.129
• InChiKey: RNFNILRTCKPWLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.04
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.9
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-acetamido-3-methylbenzimidazolium bromide 、 mercury(II) diacetate 在 NaCH₃COO 作用下， 以 乙腈 为溶剂， 以44%的产率得到[(1-(methylacetamido)-3-(methylbenzimidazol-2-ylidene))2Hg][HgBr4]
  参考文献：
  名称：

  Synthesis and structures of polymeric silver and mercury complexes with amido-functionalized N-heterocyclic carbenes

  摘要：

  Four amido-functionalized N-heterocyclic silver(I) and mercury(II) carbene complexes, [(CH3-imy-CH2CONH2)(2)Ag2Br2] (3), [Ag(CH3-bimy-CH2CONH2)(2)](4)[Ag4Br8] (4), [Hg(CH3-imy-CH2CONH2)(2)][HgBr4] (5), and [Hg(CH3-bimy-CH2CONH2)(2)][HgBr4(]) (6), have been synthesized and structurally characterized. Crystal packing revealed a 2D polymeric structure of complex 3. In addition to a repeated interaction between the Ag2Br2 units responsible for the 1D polymeric ladder structure, a pair of hydrogen bonding interactions between the amido groups of the adjacent molecules provided a basis for the other dimension of the polymeric chain. Complex 4 is comprised of a unique oligomeric anion [Ag4Br8](4) and four [Ag(CH3-bimy-CH2CONH2)(2)](+) cations. Crystal packing of 4 revealed a one-dimensional polymeric structure in which the cations are connected to each other through a pair of hydrogen bonding interactions between the adjacent amido groups. Compounds 5 and 6 are both ionic consisting of a mercury carbene cation and [HgBr4](2) anion. An intramolecular interaction of the amido oxygen with the mercury atom of the cation was observed in these two complexes. The interaction between the mercury of the cation and a bromide of the anion, along with the hydrogen bonding interaction of the adjacent amido groups, is responsible for the 2D polymeric structures of these two complexes in the solid state. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.03.014
• 作为产物：
  描述：

  1-甲基苯并咪唑 、 2-溴乙酰胺 以 丙酮 为溶剂， 反应 3.0h， 以84%的产率得到1-acetamido-3-methylbenzimidazolium bromide
  参考文献：
  名称：

  苯并咪唑盐作为 1,3-偶极环加成反应的起始原料或中间体

  摘要：

  已经合成了几种新的苯并咪唑盐，并通过多核 NMR 光谱对其进行了充分表征。苯并咪唑鎓盐在各种 1,3-偶极环加成反应中作为中间体出现，它们也可用作此类环加成反应中的原料。 图形摘要

  DOI：

  10.1007/s00706-021-02795-7

文献信息

• Synthesis and structures of amido-functionalized N-heterocyclic nickel(II) carbene complexes
  作者：Sheng-Jhih Lu、Hsueh-Hui Yang、Wei-Ju Chang、Hsin-Hsueh Hsueh、Yong-Chieh Lin、Fu-Chen Liu、Ivan J.B. Lin、Gene-Hsiang Lee

  DOI：10.1016/j.jorganchem.2020.121543

  日期：2020.11

  A series of bis-bidentate nickel(II) complexes [Ni(R-bimy-CH2CONH)2] (bimyH = benzimidazole; R = Me (3), Et (4), Ph (5)) bearing amido-functionalized N-heterocyclic carbene ligands, and pincer-type nickel(II) complexes [Ni(Py-bimy-CH2CONH)X] (X = Cl (6), Br (7)) bearing an amido- and pyridyl-functionalized N-heterocyclic carbene ligand were prepared. These complexes were characterized by NMR (1D and

  一系列具有氨基官能化的双齿双镍（II）配合物[Ni（R-bimy-CH 2 CONH）2 ]（bimyH =苯并咪唑； R = Me（3），Et（4），Ph（5）） N杂环卡宾配体和钳型镍（II）配合物[Ni（Py-bimy-CH 2 CONH）X]（X = Cl（6），Br（7））带有酰胺基和吡啶基官能化的N制备了杂环卡宾配体。这些配合物通过NMR（1D和2D）和单晶X射线衍射进行表征。配合物3 - 5具备Ç是卡宾配体以双双配位方式通过C2碳和NH氮与镍原子键合。在配合物6和7中，吡啶基取代基也N键合至镍金属中心，从而导致钳型配位模式。如从质子NMR谱观察到的，六元螯合环在配合物3 - 5个呈现的亚甲基部分非对映异构的质子，而C是配置所作的乙基取代基的自由旋转在4和苯基取代基在5受到相邻取代基的阻碍。还研究了这些镍基络合物在苯基溴化镁与芳基氯的熊田交叉偶联中的催化活性。结果表明，取决于所
• Efficient PEPPSI-Themed Palladium N-Heterocyclic Carbene Precatalysts for the Mizoroki–Heck Reaction
  作者：Yong-Chieh Lin、Hsin-Hsueh Hsueh、Shanker Kanne、Li-Kuang Chang、Fu-Chen Liu、Ivan J. B. Lin、Gene-Hsiang Lee、Shie-Ming Peng

  DOI：10.1021/om4003297

  日期：2013.7.22

  Two sets of six PEPPSI (pyridine enhanced precatalyst preparation, stabilization, and initiation) themed palladium complexes of amide-functionalized N-heterocydic carbenes [PdBr2(NHC)(Py)], where NHC = 1-acetamido-3-R-imidazolin-2-ylidene, 1-acetamido-3-R-benzimidazolin-2-ylidene and Py = pyridine, were prepared. Solid-state structures of all these complexes were determined by single-crystal X-ray diffraction methods. All complexes under scrutiny were found to adopt a trans arrangement with square-planar geometry. These complexes showed excellent catalytic activity toward the Mizoroki-Heck cross-coupling reaction of aryl chlorides and styrene. Benzimidazole-derived complexes exhibited better catalytic activity than imidazole-based complexes. Formation of palladium nanoparticles in the reaction mixture was evidenced by dynamic light scattering and transmission electron microscopy studies and a mercury poisoning experiment, suggesting the possible involvement of palladium nanoparticles in the catalytic reactions.