bis[1-methyl-2-(5-methylpyrid-2-yl)benzimidazol-5-yl]methane | 156878-67-0

• 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: bis[1-methyl-2-(5-methylpyrid-2-yl)benzimidazol-5-yl]methane
• 英文别名: bis{1-methyl-2-(5'-methyl-2'-pyridyl)benzimidazol-5-yl}methane；1-Methyl-5-[[1-methyl-2-(5-methylpyridin-2-yl)benzimidazol-5-yl]methyl]-2-(5-methylpyridin-2-yl)benzimidazole；1-methyl-5-[[1-methyl-2-(5-methylpyridin-2-yl)benzimidazol-5-yl]methyl]-2-(5-methylpyridin-2-yl)benzimidazole
• CAS: 156878-67-0
• 化学式: C₂₉H₂₆N₆
• 分子量: 458.566
• InChiKey: RYYAPMZHOUORLW-UHFFFAOYSA-N

物化性质

• 沸点：
  720.1±70.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cobalt(II) perchlorate hexahydrate 、 bis[1-methyl-2-(5-methylpyrid-2-yl)benzimidazol-5-yl]methane 以 二氯甲烷 、 乙腈 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  Piguet, Claude; Bernardinelli, Gérald; Bocquet, Bernard, Inorganic Chemistry, 1994, vol. 33, # 18, p. 4112 - 4121

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基-2-甲酸吡啶 在 盐酸 、 氯化亚砜 、 铁粉 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 bis[1-methyl-2-(5-methylpyrid-2-yl)benzimidazol-5-yl]methane
  参考文献：
  名称：

  A Comparison of the Lability of Mononuclear Octahedral and Dinuclear Triple-Helical Complexes of Cobalt(II)

  摘要：

  The lability of the mononuclear octahedral complex tris(5-methyl-2-(1'-methylbenzimidazol-2-yl)-pyridine)-cobalt(II), [Co(2)(3)](2+), is compared with the dinuclear triple-helical complex tris[bis[1-methyl-2-(5'-methylpyrid-2'-yl]benzimidazol-5-yl]methane]dicobalt(II), [Co-2(1a)(3)](4+).[Co(2)(3)](2+) undergoes rapid isomerization between mer and fac forms (k(298)(mer-fac) = 1.6 +/- 0.2 s(-1)) in acetonitrile while the racemization of (-)(589)-[Co-2(1a)(3)](4+) is roughly 10(5) times slower (k(298) = 1.4 +/- 2 10(-5) s(-1)). The pressure dependence of the isomerization of [Co(2)(3)](2+) suggests a dissociatively activated process. The racemization of (-)(589)-[Co-2(1a)(3)](4+) is found to be independent of pH above pH 4, and is not affected by added cobalt(II) or a change of solvent. Ligand exchange between [Co-2(1b)(3)](4+) (1b = bis[1-ethyl-2-(5'-methylpyrid-2'-yl)benzimidazol-5-yl]methane) and free la may be followed by electrospray mass spectrocopy and establishes the mechanism of formation of the triple helix to be initial formation of mononuclear [Co(1a)(3)](2+) followed by capping by a second cobalt to give [Co-2(1a)(3)](4+). The slow racemization of (-)(589)-[Co-2-(1a)(3)](4+) is attributed to the very slow dissociation of a cobalt ion from the triple helix: This inertness is attributed to the rigidity of the ligand and the tight pitch of the helix.

  DOI：

  10.1021/ja963693l

文献信息

• Synthesis, structure and resolution of a dinuclear Co III triple helix
  作者：Lo�c J. Charbonniere、G�rald Bernardinelli、Claude Piguet、Alan M. Sargeson、Alan F. Williams

  DOI：10.1039/c39940001419

  日期：——

  For the first time a helical dinuclear metal complex has been separated into enantiomers by transformation of a labile cobalt(II) triple-helical complex into the kinetically stable cobalt(III) complex [Co2(2a)3]6+ which has been characterized structurally and resolved by chromatography.

  首次通过将不稳定的钴（II）三螺旋复合物转化为动力学稳定的钴（III）复合物[Co2(2a)3]6+，将螺旋双核金属复合物分离为对映体。该复合物已通过色谱法进行了结构表征和解剖。
• Thermal Spin Crossover in Binuclear Iron(II) Helicates:  Negative Cooperativity and a Mixed Spin State in Solution
  作者：Shane G. Telfer、Bernard Bocquet、Alan F. Williams

  DOI：10.1021/ic015521h

  日期：2001.9.1

  Comparison of the thermal spin crossover transition in solution of a Fe(II) dinuclear triple helicate with the analogous mononuclear complex shows that the helicate transition takes place over a wider temperature range in a two step process, implying negative cooperativity.
• Unexpected kinetic stability of a dinuclear helical complex
  作者：Loïc J. Charbonnière、Marie-Fabiola Gilet、Klaus Bernauer、Alan F. Williams

  DOI：10.1039/cc9960000039

  日期：——

  The circular dichroism spectrum of a chiral dinuclear cobalt(II) triple helix is reported, together with the kinetics of racemisation which are much slower than usual for cobalt(II).
• A Comparison of the Lability of Mononuclear Octahedral and Dinuclear Triple-Helical Complexes of Cobalt(II)
  作者：Loïc J. Charbonnière、Alan F. Williams、Urban Frey、André E. Merbach、Philippe Kamalaprija、Olivier Schaad

  DOI：10.1021/ja963693l

  日期：1997.3.1

  The lability of the mononuclear octahedral complex tris(5-methyl-2-(1'-methylbenzimidazol-2-yl)-pyridine)-cobalt(II), [Co(2)(3)](2+), is compared with the dinuclear triple-helical complex tris[bis[1-methyl-2-(5'-methylpyrid-2'-yl]benzimidazol-5-yl]methane]dicobalt(II), [Co-2(1a)(3)](4+).[Co(2)(3)](2+) undergoes rapid isomerization between mer and fac forms (k(298)(mer-fac) = 1.6 +/- 0.2 s(-1)) in acetonitrile while the racemization of (-)(589)-[Co-2(1a)(3)](4+) is roughly 10(5) times slower (k(298) = 1.4 +/- 2 10(-5) s(-1)). The pressure dependence of the isomerization of [Co(2)(3)](2+) suggests a dissociatively activated process. The racemization of (-)(589)-[Co-2(1a)(3)](4+) is found to be independent of pH above pH 4, and is not affected by added cobalt(II) or a change of solvent. Ligand exchange between [Co-2(1b)(3)](4+) (1b = bis[1-ethyl-2-(5'-methylpyrid-2'-yl)benzimidazol-5-yl]methane) and free la may be followed by electrospray mass spectrocopy and establishes the mechanism of formation of the triple helix to be initial formation of mononuclear [Co(1a)(3)](2+) followed by capping by a second cobalt to give [Co-2(1a)(3)](4+). The slow racemization of (-)(589)-[Co-2-(1a)(3)](4+) is attributed to the very slow dissociation of a cobalt ion from the triple helix: This inertness is attributed to the rigidity of the ligand and the tight pitch of the helix.
• Piguet, Claude; Bernardinelli, Gérald; Bocquet, Bernard, Inorganic Chemistry, 1994, vol. 33, # 18, p. 4112 - 4121
  作者：Piguet, Claude、Bernardinelli, Gérald、Bocquet, Bernard、Schaad, Olivier、Williams, Alan F.

  DOI：——

  日期：——