N,N'-bis(pyridine-2-carboxamido)-4-methylbenzene | 216389-73-0

• 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: N,N'-bis(pyridine-2-carboxamido)-4-methylbenzene
• 英文别名: N,N-bis(pyridine-2-carboxamido)-4-methylbenzene；N,N'-(4-methyl-1,2-phenylene)dipicolinamide；3,4-bis(pyridine-2-carboxamido)toluene；H2Mebpb；N-[4-methyl-2-(pyridine-2-carbonylamino)phenyl]pyridine-2-carboxamide
• CAS: 216389-73-0
• 化学式: C₁₉H₁₆N₄O₂
• 分子量: 332.362
• InChiKey: IVPORCBJZZXYBD-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  397.4±42.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  nickel(II) acetate tetrahydrate 、 N,N'-bis(pyridine-2-carboxamido)-4-methylbenzene 以 乙醇 、 丙酮 为溶剂， 以80%的产率得到[Ni(N,N'-bis(pyridine-2-carboxamido)-4-methylbenzene(-2H))]
  参考文献：
  名称：

  Structural effects on electrochemical properties of the carboxamide complexes [NiII(Mebpb)] and [NiII(Mebqb)]

  摘要：

  Two Ni(II) complexes of the dianionic ligands, Mebpb(2-) , [H(2)Mebpb = N,N'-bis(pyridine-2-carboxamido)-4- methylbenzene] and Mebqb(2-), [H(2)Mebqb = N,N'-bis(quinoline-2-carboxamido)-4-methylbenzene] have been synthesized and characterized by elemental analyses, IR, and UV-Vis spectroscopy. The crystal and molecular structures of [Ni(Mebpb)], (1), and [Ni(Mebqb)], (2), were determined by X-ray crystallography. Both complexes exhibit distorted square-planar NiN4 coordination figures with two short and two long Ni-N bonds (Ni-N similar to 1.84 and similar to 1.95 angstrom, respectively). The electrochemical behavior of these complexes with the goal of evaluating the structural effects on the redox properties has been studied. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.05.020
• 作为产物：
  描述：

  2-吡啶甲酸 、 3,4-二氨基甲苯 在 亚磷酸三苯酯 作用下， 以 吡啶 为溶剂， 反应 0.08h， 以98%的产率得到N,N'-bis(pyridine-2-carboxamido)-4-methylbenzene
  参考文献：
  名称：

  二吡啶甲酰胺锰配合物的声化学制备及其在酮声合成催化剂中的应用

  摘要：

  通过氯化锰（II）和双酰胺（2-吡啶甲酸和邻苯二胺的缩合产物）的超声处理，合成了一系列非血红素锰络合物。在超声辐射下，乙酸作为添加剂，使用生态友好的过氧化氢，锰配合物可有效促进未活化的脂肪族和苄基CH-H和N-杂环底物的氧化，催化剂负载量低。色谱研究表明，相应的酮是唯一可检测到的产物。值得注意的是，催化剂结构中电子给体的存在显着提高了反应产率。通过添加紫罗兰醇（2,6-二-氧化反应产率的实质性降低叔丁基-4-甲基苯酚）作为自由基陷阱，表明存在自由基反应途径。

  DOI：

  10.1002/jhet.3518

文献信息

• New pyridine carboxamide ligands and their complexation to copper(ii). X-Ray crystal structures of mono-, di, tri- and tetranuclear copper complexes
  作者：Sneh L. Jain、Pravat Bhattacharyya、Heather L. Milton、Alexandra M. Z. Slawin、Joe A. Crayston、J. Derek Woollins

  DOI：10.1039/b316519a

  日期：——

  do)pyridine (H2L6) and 2,6-bis(pyridine-2-carboxamido)pyridine (H2L7) reacted with copper(II) acetate monohydrate to give tricopper(II) complexes [Cu3(L)2(μ2-OAc)2]. X-Ray crystallography confirmed deprotonation of the amidic nitrogen atoms and that the (L6,7)2− ligands and acetate anions hold three copper(II) ions in approximately linear fashion. H2L8. Reacted with copper(II) tetrakis(pyridine) perchlorate

  七个新的吡啶二甲酰胺 配体H 2 L 1–7是通过缩合反应合成的，包括吡啶-2,6-二羧酸（H 2 dipic），吡啶-2,6-二羰基二氯化物 或者 2,6-二氨基吡啶 带有杂环 胺 或者 羧酸前体。的晶体学分析N，N'-双（2-吡啶基）吡啶-2,6-二甲酰胺一水合物（H 2 L 8 ·H 2 O），N，N′-双[2-（2-吡啶基）甲基]吡啶-2，6-二甲酰胺和N，N'-双[2-（2-吡啶基）乙基]吡啶-2,6-二甲酰胺一水合物 揭示了广泛的分子内氢键相互作用。 2,6-双（吡嗪-2-羧酰胺基）吡啶（H 2 L 6）和2,6-双（吡啶-2-甲酰胺基）吡啶（H 2 L 7）与一水合乙酸铜（II）得到tricopper（II）配合物[铜3（L）2（μ 2 -OAc）2 ]。X射线晶体学 确认酰胺的去质子化 氮原子并且（L 6,7）2− 配体和醋酸根阴离子保持3铜（II）离子在大致线性的方式。H
• Synthesis, characterization and electrochemistry of carboxamido Co(III) complexes: The crystal structure of [CoIII(Mebpb)(N-MeIm)2]BPh4·CH3OH
  作者：Soraia Meghdadi、Mehdi Amirnasr、Kurt Mereiter、Ahmad Amiri、Vahid Ghodsi

  DOI：10.1016/j.ica.2010.01.007

  日期：2010.4

  Three cobalt(III) complexes of the type trans-[CoIII(Mebpb)(amine)2]X Mebpb2− = N,N′-bis(pyridine-2-carboxamido)-4-methylbenzene dianion, and amine = N-methylimidazole (N-MeIm) (1), 3-methylpyridine (3-MePy) (2), 3-acetylpyridine (3-AcPy) (3), X = BPh4- (1), ClO4- (2, 3)} were synthesized and characterized by elemental analyses, IR, UV–Vis, and 1H NMR spectroscopy. The structure of 1·CH3OH was determined

  的类型的三钴（III）配合物的反式- [CO III（Mebpb）（胺）2 ] X Mebpb 2-  =  N，N-双（吡啶-2-甲酰氨基）-4-甲基苯的二价阴离子，和胺=  N-甲基咪唑（N -MeIm）（1），3-甲基吡啶（3-MePy）（2），3-乙酰基吡啶（3-AcPy）（3），X = BPh4- （1），ClO4- （2，3）}是通过元素分析，IR，UV-Vis和1 H NMR光谱合成和表征的。1 ·CH 3的结构OH由X射线晶体学测定，发现在Co周围具有扭曲的八面体几何形状。还报道了这些络合物的电化学行为，目的是评估轴向连接对氧化还原性能的影响。Co（III）的还原电势从（1）的-0.63 V到（3）的-0.20 V，显示出与轴向配体的σ供体能力相对较好的相关性。
• Steric effect on construction of Cu(II) complexes with pyridine carboxamide ligands
  作者：Do Nam Lee、Ji Young Ryu、Han Kwak、Young Min Lee、Sun Hwa Lee、Jung In Poong、Junghyun Lee、Woonsup Shin、Cheal Kim、Sung-Jin Kim、Youngmee Kim

  DOI：10.1016/j.molstruc.2007.10.006

  日期：2008.8

  The structures of three new Cu(II) complexes with pyridine carboxamide ligands (Me(2)bpb, 6-Me-2-Mebpb, and 6-Me-2-Me(2)bpb) have been determined. 6-Methyl-substituted pyridyl bpb ligands produced dimeric compounds with Cu(II) ions, and weak interactions between dimers can make even polymeric compounds, while bpb ligands without 6-methyl substitution produced monomeric Cu(II) complexes. The large distortion effects of 6-methyl-substitution are shown in Cu(II) complexes with 6-methyl-substituted pyridyl bpb ligands. This result suggests that the steric effect of 6-methyl-substitution plays important role for distortion of the structure, and 6-methyl-substitution can also influence to make polymeric compounds with interactions between Cu(II) ions and neighbor carbonyl oxygen atoms. In addition, the voltammetric behaviors of the Cu complexes were examined and classified into two groups, with/without 6-methyl group. The complexes without 6-methyl group show reversible redox waves at similar to-1.6 V, and the complexes with 6-methyl group do irreversible redox ones at similar to-1.3 V, indicating that the presence of the methyl group of 6-position of the complex makes the reduction of the complexes easier. (C) 2007 Elsevier B.V. All rights reserved.
• Synthesis, structure, and electrochemistry of pyridinecarboxamide cobalt(III) complexes; the effect of bridge substituents on the redox properties
  作者：Soraia Meghdadi、Mehdi Amirnasr、Mohammad H. Habibi、Ahmad Amiri、Vahid Ghodsi、Azadeh Rohani、Ross W. Harrington、William Clegg

  DOI：10.1016/j.poly.2008.05.031

  日期：2008.9

  Two series of complexes of the types trans-[Co-III(Mebpb)(amine)(2)]ClO4 [Mebpb(2-) = N,N-bis(pyridine-2carboxamido)-4-methylbenzene dianion, and annine = pyrrolidine (prldn) (1a), piperidine (pprdn) (2a), morpholine (mrpln) (3a), benzylamine (bzlan) (4a)), and trans-[Co-III(cbpb)(amine)(2)]X cbpb(2-) = N,N-bis(pyridine-2-carboxamido)-4-chlorobenzene dianion, and arnine = pyrrolidine (prldn), X = PF6 (1b), piperidine (pprdn), X = PF6 (2b), morpholine (mrpln), X = ClO4 (3b), benzylamine (bzlan), X = PF6 (4b)) have been synthesized and characterized by elemental analyses, IR, UV-Vis, and H-1 NMR spectroscopy. The crystal structure of la has been determined by X-ray diffraction. The electrochemical behavior of these complexes, with the goal of evaluating the effect of axial ligation and equatorial substitution on the redox properties, is also reported. The reduction potential of Co-III, ranging from -0.53 V for (1a) to -0.31 V for (3a) and from -0.48 V for (1b) to -0.22 V for (3b) show a relatively good correlation with the sigma-donor ability of the axial ligands. The methyl and chloro substituents of the equatorial ligand have a considerable effect on the redox potentials of the central cobalt ion and the ligand-centered redox processes. (C) 2008 Elsevier Ltd. All rights reserved.
• Sonochemical Preparation of Dipicolinamide Mn‐complexes and Their Application as Catalysts Towards Sono‐synthesis of Ketones
  作者：Wael A. A. Arafa

  DOI：10.1002/jhet.3518

  日期：2019.4

  Noteworthy, the presence of electron donors in the catalyst structure significantly increased the reaction yields. The substantial lowering of the oxidation reaction yields by adding ionol (2,6‐di‐tert‐butyl‐4‐methylphenol) as a free radical trap suggesting a free radical reaction pathway.

  通过氯化锰（II）和双酰胺（2-吡啶甲酸和邻苯二胺的缩合产物）的超声处理，合成了一系列非血红素锰络合物。在超声辐射下，乙酸作为添加剂，使用生态友好的过氧化氢，锰配合物可有效促进未活化的脂肪族和苄基CH-H和N-杂环底物的氧化，催化剂负载量低。色谱研究表明，相应的酮是唯一可检测到的产物。值得注意的是，催化剂结构中电子给体的存在显着提高了反应产率。通过添加紫罗兰醇（2,6-二-氧化反应产率的实质性降低叔丁基-4-甲基苯酚）作为自由基陷阱，表明存在自由基反应途径。