4-methyl(pyridin-2-ylmethylene)benzohydrazide | 58809-89-5

• 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: 4-methyl(pyridin-2-ylmethylene)benzohydrazide
• 英文别名: 4-methylbenzoic acid (1-pyridin-2-ylmethylidene)hydrazide；2-pyridinecarboxaldehyde-4-methylbenzoylhydrazone；N-(p-tolyl)-N'-(picolinylidene)-hydrazine；N-(4-methylbenzoyl)-N'-(picolinylidene)hydrazine；N-(C6H4MeCO)-N'-(picolinylidene)hydrazine；4-methyl-N-(pyridin-2-ylmethylideneamino)benzamide
• CAS: 58809-89-5
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: BFDYUKVHNMLJKM-UHFFFAOYSA-N

物化性质

• 熔点：
  161-163 °C
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tris(triphenylphosphine)ruthenium(II) chloride 、 4-methyl(pyridin-2-ylmethylene)benzohydrazide 在 KOH 作用下， 以 甲醇 为溶剂， 生成 trans-[Ru(N-(C6H4MeCO)-N'-(picolinylidene)hydrazine(-H)(1-))(PPh3)2Cl]
  参考文献：
  名称：

  Some trans-chlorobis(triphenylphosphine)ruthenium(II) complexes with N,N,O-donor N-(aroyl)-N′-(picolinylidene)hydrazines

  摘要：

  The reactions of [Ru(PPh3)(3)Cl-2] and N-(aroyl)-N'-(picolinylidene)hydrazines (HL): derived from 2-pyridinecarbaldehyde and 4-substituted aroylhydrazines in boiling methanol provide mixed-ligand complexes having the general formula trans-[RuL(PPh3)(2)Cl]. The complexes were characterized by analytical, spectroscopic and electrochemical measurements. The +2 oxidation state of the metal ions in these complexes is confirmed by their diamagnetic nature in the solid state and electrically non-conducting behavior in solution. The X-ray structure of a representative complex has been determined. The metal ion is in a distorted octahedral N2OP2Cl coordination sphere. The monoanionic pyridine-N. imine-N and deprotonated amide-O donor ligand and the chlorine atom form an N2OCl square-plane around the metal centre and the P-atoms of the PPh3 Molecules OCCUPY the remaining two axial sites. The P-31 NMR spectra of all the complexes in CDCl3 solutions are consistent with the irons orientation of the PPh3 molecules. Electronic spectra of the complexes in dichloromethane solution display several bands in the range 590-261 nm due to metal-to-ligand charge transfer and intraligand transitions. Cyclic voltammograms of the complexes in dimethylformamide solution display the reversible Ru(III)/Ru(II) couple in the potential range 0.40-0.52 V (versus saturated calomel electrode). The trend in these potential values reflects the polar effect of the substituents on the aroyl moiety of the ligand (L-). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2004.09.027
• 作为产物：
  描述：

  吡啶-2-甲醛 、 对甲苯甲酰肼 以 乙醇 为溶剂， 以85%的产率得到4-methyl(pyridin-2-ylmethylene)benzohydrazide
  参考文献：
  名称：

  具有取代的的生物活性铋（III）配合物的合成，结构表征和分子对接研究

  摘要：

  具有通式的八种取代的新的铋（III）配合物（1-8）；[Bi（RCONHNCHC 5 H 4 N）Cl x ]和[Bi（RCONHNCHC 9 H 6 N）Cl x ]，其中R = C 10 H 7 O （1，和8），C 4 H 3 S （2）， C 6 H 5 O （3和6）， C 7 H 7 （4）， C 5 H 4 N （5和7），已经准备好x = 2或3。取代的腙（我1 -I 8）是由化学计量的量的各酰肼如对甲酰肼的反应来合成，4- hydroxybenzhydrazide，噻吩-2-羧酸酰肼，3-羟基-2-萘甲酸酰肼，异氰酸酰肼和合适的芳族醛，如吡啶-2-羧醛和喹啉-2-羧醛。然后将这些（配体）与Bi（III）物种络合，生成目标化合物。通过FTIR和NMR光谱对它们进行了表征，以找到有关其结构基序的明确证据。（1＆I 6）的X射线数据进一步验证合成化合物的化学结构。（1）的分子几

  DOI：

  10.1016/j.molstruc.2021.129870

文献信息

• Ruthenium(ii) complexes containing RuN4O2 spheres assembled via pyridine-imine-amide coordination. Syntheses, structures, properties and protonation behaviour of coordinated amide
  作者：Satyanarayan Pal、Samudranil Pal

  DOI：10.1039/b110912j

  日期：2002.4.26

  A series of ruthenium(II) complexes of general formula [RuL2] with the pyridine-N, the imine-N and the amide-O donor N-(aroyl)-N′-(picolinylidene)hydrazines (HL) has been synthesized. The ligands differ on the substituent at the para position of the aroyl fragment. The complexes have been characterized by analytical, 1H NMR, electronic absorption spectroscopy and cyclic voltammetry. X-Ray structures of representative complexes have been determined. The lowest energy MLCT (Ru(dπ) → L(π*)) transitions for these complexes are observed at essentially identical wavelength (544 ± 1 nm). The complexes display a metal centred oxidation and a ligand centred reduction in the potential ranges 0.44 to 0.59 V and −1.49 to −1.35 V (vs. Ag/AgCl), respectively. The differences in the metal and ligand redox potentials (ΔE1/2) are practically same (1.94 ± 0.01 V) for all the complexes. The identical MLCT band positions and the same ΔE1/2 values suggest that in this series of complexes, the energy gap between the metal-dπ and the ligand-π* levels is constant. The effective pKa values of the species obtained by protonation of the coordinated amide functionalities in one of the complexes have been evaluated by spectrophotometric titration. The corresponding diprotonated species has been characterized by X-ray crystallography.

  我们合成了一系列通式为[RuL2]的钌(II)配合物，它们具有吡啶-N、亚胺-N 和酰胺-O 供体 N-（酰基）-N′-（偏吡啶基）肼（HL）。这些配体在芳基片段对位的取代基上有所不同。这些配合物通过分析、1H NMR、电子吸收光谱和循环伏安法进行了表征。代表性复合物的 X 射线结构已经确定。这些配合物的最低能量 MLCT（Ru(dπ) → L(π*)）转变的波长（544 ± 1 nm）基本相同。在 0.44 至 0.59 V 和 -1.49 至 -1.35 V（相对于 Ag/AgCl）的电位范围内，这些配合物分别显示出以金属为中心的氧化和以配体为中心的还原。所有配合物的金属和配体氧化还原电位（ΔE1/2）几乎相同（1.94 ± 0.01 V）。相同的 MLCT 带位置和相同的 ΔE1/2 值表明，在这一系列配合物中，金属-π 级和配体-π* 级之间的能隙是恒定的。通过分光光度滴定法评估了其中一个配合物中配位酰胺官能团质子化后得到的物种的有效 pKa 值。相应的二质子化物种已通过 X 射线晶体学进行了表征。
• Mononuclear Pervanadyl (VO2+) Complexes with Tridentate Schiff Bases: Self-assemblingvia C-H…oxo and π-π Interactions
  作者：Satyanarayan Pal、Kasiraman Rinku Radhika、Samudranil Pal

  DOI：10.1002/1521-3749(200107)627:7<1631::aid-zaac1631>3.0.co;2-h

  日期：2001.7

  sind redox-aktiv und zeigen eine irreversible Reduktion (–0,64 bis –0,72 V vs. Ag/AgCl). Die Kristallstrukturen aller Verbindungen wurden bestimmt. In jedem Komplex liegt das Metallatom in einer verzerrt-trigonal-pyramidalen N2O3-Koordinationssphare vor, die aus dem Pyridin-N-Atom, dem Imin-N-Atom und dem deprotonierten Amid-O-Atom des Donors L– und zweier Oxogruppen gebildet wird. Die planaren Liganden

  描述了全氧钒 (VO2+) 与 N-(芳酰基)-N'-(吡啶甲叉基)肼（HL = Hpabh、Hpath 和 Hpadh；H 代表可离解的酰胺氢）的配合物。席夫碱分别通过 2-吡啶-甲醛与苯甲酰肼 (Hpabh)、4-甲基苯甲酰肼 (Hpath) 和 4-二甲氨基苯甲酰肼 (Hpadh) 缩合获得。[VO(acac)2]和HL在乙腈中的空气中反应得到通式[VO2L]的配合物。抗磁性和 EPR 沉默证实了这些配合物中钒的 +5 氧化态。配合物的红外光谱与配位配体的烯醇形式一致。电子光谱显示 486-233 nm 范围内的电荷转移带。这些配合物具有氧化还原活性并显示出不可逆的还原（–0.64 至 –0.72 V 与 Ag/AgCl）。已确定所有配合物的晶体结构。在每个配合物中，金属中心位于由吡啶-N、亚胺-N和去质子化的酰胺-O供体L-和两个氧代基团形成的扭曲的三角-双锥体N2O3配位球中。平
• SYNTHESES, CRYSTAL STRUCTURES AND ANTIBACTERIAL ACTIVITIES OF MONONUCLEAR NICKEL(II) COMPLEXES WITH SIMILAR SCHIFF BASES
  作者：Y.-L. Sang、X.-S. Lin、L.-F. Zou、R.-F. Jin、X.-H. Zhang、Y.-H. Liu

  DOI：10.1134/s0022476622060130

  日期：2022.6

  Abstract Two mononuclear nickel(II) complexes, [Ni(L1)2] (1) and [Ni(L2)2] (2), where L1 and L2 are the anions of 4-methylbenzoic acid (1-pyridin-2-ylmethylidene)hydrazide (HL1) and benzoic acid (1-pyridine-2-ylethylidene)hydrazide (HL2), respectively, were prepared and characterized by physico-chemical methods and single crystal X-ray diffraction. The tridentate Schiff base ligands coordinate to the

  摘要 两个单核镍 (II) 配合物 [Ni(L 1 ) 2 ] ( 1 ) 和 [Ni(L 2 ) 2 ] ( 2 )，其中 L 1和 L 2是 4-甲基苯甲酸 (1-吡啶) 的阴离子-2-基亚甲基）酰肼（HL 1）和苯甲酸（1-吡啶-2-基亚乙基）酰肼（HL 2 ）) 分别通过物理化学方法和单晶 X 射线衍射进行制备和表征。三齿席夫碱配体通过吡啶氮、亚氨基氮和烯醇化氧原子与镍原子配位。每个配合物中的Ni原子由两个席夫碱配体六个配位，形成八面体配位。为研究甲基位置对抗菌活性的影响，对这些配合物对枯草芽孢杆菌、金黄色葡萄球菌、大肠杆菌和荧光假单胞菌进行了研究。
• Half‐sandwich iridium complexes: Synthesis and catalytic activity in dehydrogenation of alcohols to carboxylic acids
  作者：Lin‐Wu Ye、Zi‐Jian Yao

  DOI：10.1002/aoc.7642

  日期：2024.11

  A series of N,N-chelate half-sandwich iridium complexes were synthesized by a simple method with good yields. The dehydrogenation of a series of aromatic and aliphatic primary alcohols to corresponding carboxylic acids has been successfully achieved by the prepared air stable iridium complexes under mild reaction conditions. Carboxylic acids were obtained in high yields under open flask condition with

  通过一种简单的方法合成了一系列 N，N-螯合物半夹心铱配合物，产率良好。制备的空气稳定铱配合物在温和的反应条件下成功地实现了一系列芳香族和脂肪族伯醇脱氢成相应的羧酸。在开瓶条件下以高产率获得羧酸，具有广泛的底物和对敏感官能团的良好耐受性。这种半夹层铱催化剂系统显示出理想的稳定性和催化活性，并且在仅 0.05 mol% 的极低催化剂负载量下可以观察到 372.0 h-1 的高 TOF。此外，这种可持续催化剂可以重复使用至少 5 次循环，而不会明显失去其活性，突出了其在工业中的潜在应用。通过单晶 X 射线分析确定 N，N-螯合物铱复合物 1 和 3 的结构。
• Preparation and characterization of acylhydrazone nickel(II) complexes and their catalytic behavior in vinyl polymerization of norbornene and oligomerization of ethylene
  作者：Junxian Hou、Wen-Hua Sun、Dongheng Zhang、Liyi Chen、Wei Li、Dongfeng Zhao、Haibin Song

  DOI：10.1016/j.molcata.2005.01.009

  日期：2005.4

  The derivatives of 4,5-diazafluorene-9-one-benzoylhydrazone (1-4) and 2-pyridine-carboxaldehyde-benzoylhydrazone (5-9) were prepared. The compounds 1-4 reacted with Ni(Ac)(2)(.)4H(2)O to form diaquabis [4,5-diazafluorene-9-one-benzoylhydrazone] nickel (II) (10-13), while the compounds 5-9 reacted with (DME)NiBr2 to form bis[N-(pyridine-2-carboxaldehyde-benzoylhydrazone)] nickel (II) dibromide (14-18), respectively. All ligands and complexes were characterized by elemental analysis and spectroscopic analysis, along with the X-ray single crystal diffraction techniques for 10, 13 and 14. The nickel (II) centers are six-coordinated with two corresponding ligands and two coordinated solvents for 10-13, while the geometry around the nickel atom of 14-18 is distorted octahedron with two ligands and two bromides. Activated with methylaluminoxane, all nickel complexes show good activities for vinyl polymerization of norbornene and considerable activities for ethylene oligomerization at ambient pressure. By using 10, the influence of reaction conditions was carefully examined on the catalytic behavior of vinyl polymerization of norbornene. The catalytic conditions were varied to investigate their effects on activity of ethylene oligomerization. The resulting poly(norbornene)s were characterized by IR. H-1 NMR, TGA, DSC and the viscosity measurement. (c) 2005 Elsevier B.V. All rights reserved.