1-ferrocenyl-3-methylbenzimidazolium iodide | 221293-92-1

• 英文名称: 1-ferrocenyl-3-methylbenzimidazolium iodide
• CAS: 221293-92-1
• 化学式: C₁₈H₁₇FeN₂*I
• 分子量: 444.098
• InChiKey: NHABRAMJSYKBPW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1-ferrocenyl-3-methylbenzimidazolium iodide 、 palladium diacetate 以 四氢呋喃 为溶剂， 以83%的产率得到bis[1-ferrocenyl-3-methyl-benzimidazoline-2-ylidene]diiodopalladium(II)
  参考文献：
  名称：

  ñ -杂环卡宾与Ñ -ferrocenyl- Ñ ' -甲基-取代：合成，反应性，结构和电化学

  摘要：

  具有一个N-二茂铁基取代基和一个N-甲基取代基的苯并咪唑鎓盐是通过包括金属茂基与非环状邻苯二胺-二胺前体的偶联，闭环和氧化的合成序列制备的。从这些卡宾祖先合成了一系列卡宾衍生物，包括硫脲，嗪和具有W（0），Pd（II）和Hg（II）的金属配合物。将这一系列化合物的光谱，结构和电化学性质与最近发表的类似但亚甲基间隔的苯并咪唑啉-2-亚烷基衍生物进行了比较，表明卡宾部分与N-二茂铁基取代基之间存在显着的电子连通。

  DOI：

  10.1016/s0022-328x(98)00943-7
• 作为产物：
  描述：

  、 碘甲烷 以 acetonitrile 为溶剂， 以99%的产率得到1-ferrocenyl-3-methylbenzimidazolium iodide
  参考文献：
  名称：

  Redox-Active N-Heterocyclic Carbenes: Design, Synthesis, and Evaluation of Their Electronic Properties

  摘要：

  To investigate effects of redox-active functional groups on the coordination chemistry and electronic properties of N-heterocyclic carbenes (NHCs), we prepared a series of complexes comprising 1,3-diferrocenylimidazolylidene and -benzimidazolylidene (1 and 2, respectively), 1-ferrocenyl-3-methyl- and 1, 3-diphenyl-5-ferrocenylbenzimidazolylidene (3 and 4, respectively), N,N'-diisobutyldiaminocarbene[3]ferrocenophane (FcDAC), and 1,3-dimesitylnaphthoquinoimidazolylidene (NqMes) ligands and coordinated [Ir(COD)Cl] (COD = 1,5-cyclooctadiene), [Ir-(CO)(2)Cl], and [M(CO)(5)] (M = Cr, Mo, W) units. The coordination chemistry of the aforementioned NHCs was investigated by X-ray crystallography, and their electronic properties were studied by NMR and IR spectroscopy, as well as electrochemistry. No significant variation in nu(CO) was observed among metal carbonyl complexes supported by 2-4 and FcDAC, indicating that the number (one vs two) or redox-active groups, the location (N atom vs backbone) of the redox-active group, and carbene ring identities (strained six-membered, nonaromatic vs five-membered, heteroaromatic) did not have a significant effect on ligand electron-donating ability. Because the shifts in nu(CO) upon oxidation of 1-3 and FcDAC were similar in magnitude but opposite in sign to NqMes, we conclude that the enhancement or attenuation of ligand donating is primarily Coulombic in origin (i.e., due to the molecule acquiring a positive or negative charge).

  DOI：

  10.1021/om900698x