3-methyl-1-(pyridin-2-yl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate(V) | 1184954-41-3

• 英文名称: 3-methyl-1-(pyridin-2-yl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate(V)
• CAS: 1184954-41-3
• 化学式: C₁₃H₁₂N₃*F₆P
• 分子量: 355.223
• InChiKey: FDNDOWUXQKZPAM-UHFFFAOYSA-N

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：

  3-methyl-1-(pyridin-2-yl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate(V) 、 五羰基氯铼(I) 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以89%的产率得到ReCl(N-methyl-N′-2-pyridylbenzimidazol-2-ylidine)(CO)₃
  参考文献：
  名称：

  Re（I）NHC配合物用于CO 2的电催化转化

  摘要：

  N-杂环卡宾结构单元周围的配体模块化构建代表了一种灵活的合成策略，可用于调节金属配合物的电子性能。在此，使用最近建立的无过渡金属技术以高收率构建甲基苯并咪唑鎓-吡啶和甲基苯并咪唑鎓-嘧啶的配体。随后螯合RECL（CO）5种配料RECL（Ñ甲基Ñ '-2- pyridylbenzimidazol -2-亚基）（CO）3和RECL（Ñ甲基Ñ '-2- pyrimidylbenzimidazol -2-亚基）（CO ）3。这些Re（I）NHC配合物能够介导CO 2的双电子转化一电子还原之后；在少量生成H 2和HCO 2 H的情况下，观察到法拉第生成CO的效率> 60％。提供了来自循环伏安法的数据，并将其与经过充分研究的ReCl（2,2'-联吡啶）（CO）3和MnBr（2,2'-联吡啶）（CO）3系统进行了比较。还讨论了密度泛函理论计算，红外光谱电化学和化学还原的结果。

  DOI：

  10.1021/acs.inorgchem.6b00079
• 作为产物：
  描述：

  3-methyl-1-(pyridin-2-yl)-1H-benzo[d]imidazol-3-ium iodide 在 ammonium hexafluorophosphate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以99%的产率得到3-methyl-1-(pyridin-2-yl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate(V)
  参考文献：
  名称：

  Re（I）NHC配合物用于CO 2的电催化转化

  摘要：

  N-杂环卡宾结构单元周围的配体模块化构建代表了一种灵活的合成策略，可用于调节金属配合物的电子性能。在此，使用最近建立的无过渡金属技术以高收率构建甲基苯并咪唑鎓-吡啶和甲基苯并咪唑鎓-嘧啶的配体。随后螯合RECL（CO）5种配料RECL（Ñ甲基Ñ '-2- pyridylbenzimidazol -2-亚基）（CO）3和RECL（Ñ甲基Ñ '-2- pyrimidylbenzimidazol -2-亚基）（CO ）3。这些Re（I）NHC配合物能够介导CO 2的双电子转化一电子还原之后；在少量生成H 2和HCO 2 H的情况下，观察到法拉第生成CO的效率> 60％。提供了来自循环伏安法的数据，并将其与经过充分研究的ReCl（2,2'-联吡啶）（CO）3和MnBr（2,2'-联吡啶）（CO）3系统进行了比较。还讨论了密度泛函理论计算，红外光谱电化学和化学还原的结果。

  DOI：

  10.1021/acs.inorgchem.6b00079

文献信息

• Ruthenium(II) carbonyl chloride complexes containing pyridine-functionalised bidentate N-heterocyclic carbenes: Synthesis, structures, and impact of the carbene ligands on catalytic activities
  作者：Xiao-Wei Li、Gao-Feng Wang、Fei Chen、Yi-Zhi Li、Xue-Tai Chen、Zi-Ling Xue

  DOI：10.1016/j.ica.2011.09.009

  日期：2011.11

  corresponding silver carbene complexes and characterized by NMR, IR spectroscopy and elemental analysis. In these complexes with bidentate Py-NHC ligands, one CO ligand is trans to the Py ligand. In 1a , 2a , 4a , and 5a , the NHC ligand is trans to the other CO ligand, thus leaving the two Cl − ligands trans to each other. In 1b , 2b , 3b , 4b , and 5b , the NHC ligands are trans to one Cl − ligand, and the two

  一系列新的钌（II）羰基氯氯化物与吡啶官能化的N-杂环卡宾[Ru（Py-NHC）（CO）2 Cl 2]，[Py-NHC = 3-甲基-1-（2-吡啶基）咪唑-2-亚烷基1（1a和1b）; 3-甲基-1-（2-吡啶基）咪唑-2-亚甲基，2（2a和2b）; 3-甲基-1-（2-吡啶基）苯并咪唑啉-2-亚甲基，3（3b）; 3-甲基-1-（2-吡啶基）苯并咪唑啉-2-亚烷基，4（4a和4b）；1-甲基-4-（2-吡啶基）-1,2,4-三唑啉-5-亚烷基，5（5a和5b）]是通过相应的银卡宾配合物进行金属转移反应制备的，并通过NMR，IR光谱和元素分析。在具有双齿Py-NHC配体的这些络合物中，一种CO配体被转化为Py配体。在1a，2a，4a和5a中，NHC配体被转化为另一个CO配体，因此使两个Cl-配体彼此转化。在1b，2b，3b，4b和5b中，NHC配体是反过来的一个Cl-配体，两个Cl-配体
• Four-coordinate N-heterocyclic carbene (NHC) copper(I) complexes with brightly luminescence properties
  作者：Shaobo Liu、Shengxian Xu、Jinglan Wang、Feng Zhao、Hongying Xia、Yibo Wang

  DOI：10.1080/00958972.2016.1278075

  日期：2017.2.16

  Abstract Three four-coordinate N-heterocyclic carbene (NHC) copper(I) complexes, [Cu(Py-Im)(POP)](PF6) (P1), [Cu(Py-BenIm)(POP)](PF6) (P2), and [Cu(Py-c-BenIm)(POP)](PF6) (P3) (Py-Im = 3-methyl-1-(pyridin-2-yl)-1H-imidazolylidene, Py-BenIm = 3-methyl-1-(pyridin-2-yl)-1H-benzo[d]imidazolylidene, Py-c-BenIm = 3-methyl-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazolylidene, POP = bis([2-diphenylphosphino]-phenyl)ether)

  摘要 三种四配位 N-杂环卡宾 (NHC) 铜 (I) 配合物 [Cu(Py-Im)(POP)](PF6) (P1), [Cu(Py-BenIm)(POP)](PF6) (P2) 和 [Cu(Py-c-BenIm)(POP)](PF6) (P3) (Py-Im = 3-methyl-1-(pyridin-2-yl)-1H-imidazolylidene, Py-BenIm = 3-methyl-1-(pyridin-2-yl)-1H-benzo[d]imidazolylidene, Py-c-BenIm = 3-methyl-1-(pyridin-2-ylmethyl)-1H-benzo[d]imidazolylidene , POP = bis([2-diphenylphosphino]-phenyl)ether)，首次在没有 NHC-Ag(I) 络合物金属转移的情况下合成。已通过光谱方法系统地研究了所得
• Pyridine-NHC: Effective Ligand in Pd-Catalyzed Cyclopropanation of Esters with Substituted Allyl Carbonates
  作者：Jian-Qiang Huang、Chang-Hua Ding、Xue-Long Hou

  DOI：10.1021/jo5018712

  日期：2014.12.19

  By consideration of the mechanism of Pd-catalyzed cyclopropanation and allylation, NHC-pyridine compounds were adopted as the ligand in Pd-catalyzed cyclopropanation of esters and monosubstituted allylic reagents. The corresponding cyclopropanes were afforded as major products in moderate to good yields with high cyclopropane/allylation selectivity.
• Electrochemiluminescent Ruthenium(II) <i>N</i>-Heterocyclic Carbene Complexes: a Combined Experimental and Theoretical Study
  作者：Gregory J. Barbante、Paul S. Francis、Conor F. Hogan、Peyman R. Kheradmand、David J. D. Wilson、Peter J. Barnard

  DOI：10.1021/ic400263r

  日期：2013.7.1

  A series of four Ru(II) complexes of the form [Ru(bpy)(2)((CN)-N-boolean AND)](2+) (where CAN is a bidentate pyridine-functionalized imidazolylidene- or benzimidazolylidene-based N-heterocyclic carbene (NHC) ligand and bpy is 2,2'-bipyridine) have been synthesized using a Ag(I) transmetalation protocol from the Ru(II) precursor compound, Ru(bpy)(2)Cl-2. The synthesized azolium salts and Ru(II) complexes were characterized by elemental analysis, H-1 and C-13 NMR spectroscopy, cyclic voltammetry, and electronic absorption and emission spectroscopy. The molecular structures for two benzimidazolium salts and three Ru(II) complexes were determined by single crystal X-ray diffraction. The complexes display photoluminescence within the range 611-629 nm, with the emission wavelength of the benzimidazolylidene containing structures, slightly blue-shifted relative to the imidazolylidene containing complexes. All complexes exhibited a reversible, one-electron oxidation, which is assigned to the Ru2+/3+ redox couple. When compared to [Ru(bpy)(3)](2+), complexes of imidazolylidene containing ligands were oxidized at more negative potentials, while those of the benzimidazolylidene containing ligands were oxidized at more positive potentials. All four complexes exhibited moderately intense electrochemiluminescence (ECL) with the obtained ECL spectra closely resembling the photoluminescence spectra. The ability to predictably fine-tune the highest occupied molecular orbital (HOMO) level of the Ru(II) complexes via the flexible synthetic strategy offered by NHCs is valuable for the design of ECL-based multiplexed detection strategies.
• Synthesis, Photo-, and Electrochemistry of Ruthenium Bis(bipyridine) Complexes Comprising a <i>N-</i>heterocyclic Carbene Ligand
  作者：Vivienne Leigh、Wadih Ghattas、Ralte Lalrempuia、Helge Müller-Bunz、Mary T. Pryce、Martin Albrecht

  DOI：10.1021/ic400347r

  日期：2013.5.6

  Analogues of [Ru(bpy)(3)](2+) were prepared in which one pyridine ligand site is substituted by a N-heterocyclic carbene (NHC) ligand, that is, either by an imidazolylidene with a variable wingtip group R (R = Me, 3a; R = Et, 3b; R = iPr, 3c), or by a benzimidazolylidene (Me wingtip group, 3d), or by a 1,2,3-triazolylidene (Me wingtip group, 3e). All complexes were characterized spectroscopically, photophysically, and electrochemically. An increase of the size of the wingtip groups from Me to Et or iPr groups distorts the octahedral geometry (NMR spectroscopy) and curtails the reversibility of the ruthenium oxidation. NHC ligands with methyl wingtip groups display reversible ruthenium oxidation at a potential that reflects the donor properties of the NHC ligand (triazolylidene > imidazolylidene > benzimidazolylidene). The most attractive properties were measured for the triazolylidene ruthenium complex 3e, featuring the smallest gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in the series (2.41 eV), a slightly red-shifted absorption profile, and reasonable excited-state lifetime (188 ns) when compared to [Ru(bpy)(3)](2+). These features demonstrate the potential utility of triazolylidene ruthenium complexes as photosensitizers for solar energy conversion.