1-n-butyl-3-isopropyl-benzimidazolium iodide | 1357364-11-4

• 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-n-butyl-3-isopropyl-benzimidazolium iodide
• CAS: 1357364-11-4
• 化学式: C₁₄H₂₁N₂*I
• 分子量: 344.239
• InChiKey: ABUCURTVSSUILY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  cis-dichloro-2-(phenylazo)pyridine palladium(II) 、 1-n-butyl-3-isopropyl-benzimidazolium iodide 在 NaOAc 作用下， 以 乙腈 为溶剂， 以41%的产率得到[PdI2(η1-phenylazapyridine)(1-n-butyl-3-isopropylbenzimidazolin-2-ylidene)]
  参考文献：
  名称：

  Characterization of [Pd(pap)(NHC)I2]n (n=+1, 0, −1; pap=phenylazopyridine; NHC=N-heterocyclic carbene): Unusual coordination mode of pap and non-innocent behavior of NHC

  摘要：

  The compounds [Pd(pap)(NHC)I-2], 1 and 2 (pap = Phenylazopyridine, NHC = 1,3-di-n-butyl-benzimidazolin-2-ylidene, 1 and NHC = 1-n-butyl-3-isopropyl-benzimidazolin-2-ylidene, 2) were synthesized from the respective 1,3-disubstituted benzimidazolium salts and [Pd(pap)] precursor in the presence of a base. Crystallographic characterization of 1 shows an unusual coordination mode of pap, with the ligand coordinating to the Pd(II) center only through the pyridine nitrogen atom in an eta(1)-N fashion. Both the nitrogen atoms of the azo group remain uncoordinated to the metal center. Cyclic voltammetry of 1 and 2 shows two oxidation and two reduction steps. A combination of UV-Vis and EPR spectroelectrochemistry is used to show that the reduction steps are pap based, proving its known non-innocent character. Investigation of the first oxidation step points to an electron removal from a predominantly NHC based orbital, thus showing the potential non-innocent nature of these ligands. These results can provide new mechanistic insights into the use of Pd-NHC catalysts for cross-coupling reactions, where oxidative addition is one of the deciding steps for catalysis. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.10.012