5-methylpyridine-2-carboxylic acid N-methyl-N-(2-nitrophenyl)amide | 186381-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methylpyridine-2-carboxylic acid N-methyl-N-(2-nitrophenyl)amide
• 英文别名: N,5-dimethyl-N-(2-nitrophenyl)pyridine-2-carboxamide
• CAS: 186381-21-5
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: MYKHVZOVCOJOLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.34
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-methylpyridine-2-carboxylic acid N-methyl-N-(2-nitrophenyl)amide 在 盐酸 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以86%的产率得到5-methyl-2-(1-methylbenzimidazol-2-yl)pyridine
  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
• 作为产物：
  描述：

  5-甲基-2-甲酸吡啶 在 草酰氯 、 N,N-二异丙基乙胺 作用下， 生成 5-methylpyridine-2-carboxylic acid N-methyl-N-(2-nitrophenyl)amide
  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