N-methyl-2-(5-methylpyrazin-2-yl)benzimidazole

• 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: N-methyl-2-(5-methylpyrazin-2-yl)benzimidazole
• 英文别名: 1-Methyl-2-(5-methylpyrazin-2-yl)benzimidazole；1-methyl-2-(5-methylpyrazin-2-yl)benzimidazole
• 化学式: C₁₃H₁₂N₄
• 分子量: 224.265
• InChiKey: WXZTZQWIEUOQHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  iron(II) triflate 、 N-methyl-2-(5-methylpyrazin-2-yl)benzimidazole 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  了解自旋交叉复合物中子午线与脸部异构体的影响

  摘要：

  乙腈中二价铁周围非对称二齿酸吡嗪-苯并咪唑（L1）或吡啶-苯并咪唑（L2）N-供体配体的螯合产生稳定的均相三螺旋自旋交换[Fe（L k）3 ] 2+配合物在NMR时标上缓慢交换的子午（C 1对称）和面部（C 3对称）异构体的混合物。形态偏离预期的统计比mer / fac = 3：1，该趋势分配给热力学反演影响力与溶剂化作用相结合。因此，所观察到的自旋状态的Fe II低自旋↔Fe II高自旋中出现平衡的[Fe（大号ķ）3 ] 2+是指在溶液中的复合物的混合物，一个问题通常不是这方面考虑，但其限制合理的结构特性相关性。利用非限制性相关自旋交联d-螺旋（HHH）-[LnFe（L k）3 ] 5+（Ln是三价镧系元素，L k = L5）中同构面部异构体的选择性和定量形成的优势（L6），我们提出了一种新颖的策略，为每个自旋交叉的三螺旋异构体分配相关的热力学驱动力。自旋状态平衡不同焓贡献在发现聚体-的[Fe（大号ķ）3

  DOI：

  10.1002/chem.201804161
• 作为产物：
  描述：

  5-甲基吡嗪-2-羧酸 在 sodium dithionite 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 N-methyl-2-(5-methylpyrazin-2-yl)benzimidazole
  参考文献：
  名称：

  Thermodynamic N-Donor trans Influence in Labile Pseudo-Octahedral Zinc Complexes: A Delusion?

  摘要：

  While the forces responsible for the chelate effect are well-established in coordination chemistry, the origin and implementation of the related thermodynamic trans influence remains debatable. This work illustrates a simple approach for quantifying this effect in labile pseudo-octahedral [Zn(Lk)(3)](2+) complexes lacking stereochemical preferences (Lk = L1L4 are unsymmetrical didentate a,a'-diimine ligands). In line with statistics, the triply degenerated meridional isomers mer-[Zn(Lk)(3)](2+) are stabilized by 0.8 = Delta G(exch)(mer)<= = 4.2 kJ/mol over their nondegenerated facial analogues fac-[Zn(Lk)(3)](2+) and therefore display no apparent trans influence at room temperature. However, the dissection of the free energy terms into opposite enthalpic (favoring the facial isomers) and entropic (favoring the meridional isomers) contributions reveals a trans influence assigned to solvation processes occurring in polar solvents. Altogether, the thermodynamic trans influence operating in [Zn(alpha,alpha'-diimine)(3)](2+) complexes is 12 orders of magnitude smaller than the chelate effect. A weak templating effect provided by a noncovalent lanthanide tripod is thus large enough to produce the wanted facial isomer at room temperature.

  DOI：

  10.1021/ic5022559

文献信息

• Thermodynamic N-Donor trans Influence in Labile Pseudo-Octahedral Zinc Complexes: A Delusion?
  作者：Lilit Aboshyan-Sorgho、Timothée Lathion、Laure Guénée、Céline Besnard、Claude Piguet

  DOI：10.1021/ic5022559

  日期：2014.12.15

  While the forces responsible for the chelate effect are well-established in coordination chemistry, the origin and implementation of the related thermodynamic trans influence remains debatable. This work illustrates a simple approach for quantifying this effect in labile pseudo-octahedral [Zn(Lk)(3)](2+) complexes lacking stereochemical preferences (Lk = L1L4 are unsymmetrical didentate a,a'-diimine ligands). In line with statistics, the triply degenerated meridional isomers mer-[Zn(Lk)(3)](2+) are stabilized by 0.8 = Delta G(exch)(mer)<= = 4.2 kJ/mol over their nondegenerated facial analogues fac-[Zn(Lk)(3)](2+) and therefore display no apparent trans influence at room temperature. However, the dissection of the free energy terms into opposite enthalpic (favoring the facial isomers) and entropic (favoring the meridional isomers) contributions reveals a trans influence assigned to solvation processes occurring in polar solvents. Altogether, the thermodynamic trans influence operating in [Zn(alpha,alpha'-diimine)(3)](2+) complexes is 12 orders of magnitude smaller than the chelate effect. A weak templating effect provided by a noncovalent lanthanide tripod is thus large enough to produce the wanted facial isomer at room temperature.
• Deciphering the Influence of Meridional versus Facial Isomers in Spin Crossover Complexes
  作者：Timothée Lathion、Laure Guénée、Céline Besnard、Azzedine Bousseksou、Claude Piguet

  DOI：10.1002/chem.201804161

  日期：2018.11.13

  triple‐helical spin crossover [Fe(Lk)3]2+ complexes existing as mixtures of meridional (C1‐symmetry) and facial (C3‐symmetry) isomers in slow exchange on the NMR timescale. The speciation deviates from the expected statistical ratio mer/fac=3:1, a trend assigned to the thermodynamic trans‐influence, combined with solvation effects. Consequently, the observed spin state FeIIlow‐spin↔FeIIhigh‐spin equilibria

  乙腈中二价铁周围非对称二齿酸吡嗪-苯并咪唑（L1）或吡啶-苯并咪唑（L2）N-供体配体的螯合产生稳定的均相三螺旋自旋交换[Fe（L k）3 ] 2+配合物在NMR时标上缓慢交换的子午（C 1对称）和面部（C 3对称）异构体的混合物。形态偏离预期的统计比mer / fac = 3：1，该趋势分配给热力学反演影响力与溶剂化作用相结合。因此，所观察到的自旋状态的Fe II低自旋↔Fe II高自旋中出现平衡的[Fe（大号ķ）3 ] 2+是指在溶液中的复合物的混合物，一个问题通常不是这方面考虑，但其限制合理的结构特性相关性。利用非限制性相关自旋交联d-螺旋（HHH）-[LnFe（L k）3 ] 5+（Ln是三价镧系元素，L k = L5）中同构面部异构体的选择性和定量形成的优势（L6），我们提出了一种新颖的策略，为每个自旋交叉的三螺旋异构体分配相关的热力学驱动力。自旋状态平衡不同焓贡献在发现聚体-的[Fe（大号ķ）3