2-pyridine-carboxaldehyde 4-dimethylaminobenzoylhydrazone | 109353-10-8

• 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: 2-pyridine-carboxaldehyde 4-dimethylaminobenzoylhydrazone
• 英文别名: N-(4-(dimethylamino)phenyl)-N'-(picolinylidene)-hydrazine；N-(4-dimethylaminobenzoyl)-N'-(picolinylidene)hydrazine；N-(C6H4NMe2CO)-N'-(picolinylidene)hydrazine；4-(dimethylamino)-N-(pyridin-2-ylmethylideneamino)benzamide
• CAS: 109353-10-8
• 化学式: C₁₅H₁₆N₄O
• 分子量: 268.318
• InChiKey: PCBFIUXFHFMWGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tris(triphenylphosphine)ruthenium(II) chloride 、 2-pyridine-carboxaldehyde 4-dimethylaminobenzoylhydrazone 在 KOH 作用下， 以 甲醇 为溶剂， 生成 trans-[Ru(N-(C6H4NMe2CO)-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 、 对二甲氨基苯甲酰肼 在 三氟乙酸 作用下， 以 乙醇 为溶剂， 以38.2 mmol的产率得到2-pyridine-carboxaldehyde 4-dimethylaminobenzoylhydrazone
  参考文献：
  名称：

  有机化合物及其制备方法、显示基板和显示装置

  摘要：

  公开一种有机化合物及其制备方法、显示基板和显示装置，涉及显示技术领域，用于提高显示装置的显示效果与使用寿命。该有机化合物的结构式如下式(I)所示：

  公开号：

  CN114369059A

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
• Copper(II)-activated transformation of azomethine to imidate: synthetic and structural studies
  作者：Nimma Rajaiah Sangeetha、Satyanarayan Pal、Samudranil Pal

  DOI：10.1016/s0277-5387(00)00595-7

  日期：2000.12

  The Schiff base 2-pyridine-carboxaldehyde 4-dimethylaminobenzoylhydrazone (HL, 1) was prepared by reacting 2-pyridine-carboxaldehyde and 4-dimethylaminobenzoylhydrazine in a 1:1 molar ratio in methanol. Reaction of HL (1) with Cu(O2CCH3)(2).H2O (in a 1:1 molar ratio) in methanol afforded a dinuclear copper(II) complex, [Cu-2(mu -O2CCH3)(2)L'(S)]. 2H(2)O (2). The azomethine functionality (-CH=N-) of 1 is converted to imidate (-C(OMe)=N-) in the complexed ligand L'(-). Molecular structures of both 1 and 2 were determined by X-ray crystallographic studies. The dinuclear molecule of 2 is centrosymmetric and contains two monoatomic bridging acetate groups. Each copper(II) centre is in a square-pyramidal N2O3 coordination sphere. The ligand, L'(-) coordinates the metal ion via the pyridine-N, the imidate-N, and the deprotonated amide-O atoms. One of the acetate oxygen atoms completes the N2O2 square-plane. The oxygen of the symmetry-related acetate fills the apical coordination site. Structural parameters are consistent with both copper ions being in a +2 oxidation state. The room temperature magnetic moment is 1.89 mu (B) (per Cu). In powder phase the complex displays an axial EPR spectrum at 298 K. The complex is nonconducting in methanol solution. The electronic spectrum shows a ligand field absorption at 680 nm and charge transfer bands in the range 426-215 nm. (C) 2000 Elsevier Science B.V. All rights reserved.
• Sreerama, Subramanya Gupta; Shyamraj, Dharavath; Pal, Satyanarayan, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2003, vol. 42, # 9, p. 2352 - 2358
  作者：Sreerama, Subramanya Gupta、Shyamraj, Dharavath、Pal, Satyanarayan、Pal, Samudranil

  DOI：——

  日期：——
• Some trans-chlorobis(triphenylphosphine)ruthenium(II) complexes with N,N,O-donor N-(aroyl)-N′-(picolinylidene)hydrazines
  作者：Raji Raveendran、Samudranil Pal

  DOI：10.1016/j.poly.2004.09.027

  日期：2005.1

  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.