pyridine-2-carboxylic acid [(2-hydroxy-3-methoxyphenyl)methylene]hydrazide | 305339-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: pyridine-2-carboxylic acid [(2-hydroxy-3-methoxyphenyl)methylene]hydrazide
• 英文别名: 3-methoxysalicylaldehyde picoloylhydrazone；o-vanillin picolinoylhydrazone；H2ovph；N-[(2-hydroxy-3-methoxyphenyl)methylideneamino]pyridine-2-carboxamide
• CAS: 305339-15-5
• 化学式: C₁₄H₁₃N₃O₃
• mdl: MFCD00423964
• 分子量: 271.276
• InChiKey: UXQJAGOTBSVQHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dysprosium(III) nitrate hexahydrate 、 pyridine-2-carboxylic acid [(2-hydroxy-3-methoxyphenyl)methylene]hydrazide 在 triethylamine 作用下， 以 甲醇 、 乙腈 为溶剂， 以36%的产率得到[Dy2(o-vanillin picolinoylhydrazone(2-))2(NO3)2(H2O)2]*2H2O
  参考文献：
  名称：

  Modulating Magnetic Dynamics of Three Dy₂ Complexes through Keto–Enol Tautomerism of the o-Vanillin Picolinoylhydrazone Ligand

  摘要：

  Complexation of dysprosium(III) with the hetero-donor chelating ligand o-vanillin picolinoylhydrazone (H(2)ovph) in the presence of different bases affords three new dinuclear dysprosium(III) coordination compounds, namely, [Dy-2(ovph)(2)(NO3)(2)(H2O)(2)]center dot 2H(2)O (1), [Dy-2(Hovph) (ovph) (NO3)(2)-(H2O)(4)]center dot NO3 center dot 2CH(3)OH center dot 3H(2)O (2), and Na[Dy-2(Hovph)(2)(mu(2)-OH) (OH)(H2O)(5)]center dot 3Cl center dot 3H(2)O (3), where the aroylhydrazone ligand adopts different coordination modes in respective structures depending on the reaction conditions, as revealed by single-crystal X-ray analyses to be due to their tautomeric maneuver. The magnetic properties of 1-3 are drastically distinct. Compounds 1 and 2 show single-molecule-magnet behavior, while no out alternating current signal is noticed for 3. The structural differences induced by the different coordinate fashions of the ligand may influence the strength of the local crystal field, the magnetic interactions between metal centers, and the local tensor of anisotropy on each Dy site and their relative orientations, therefore generating dissimilar dynamic magnetic behavior.

  DOI：

  10.1021/ic2014978
• 作为产物：
  描述：

  2-吡啶甲酰肼 、 邻香草醛 以 甲醇 为溶剂， 生成 pyridine-2-carboxylic acid [(2-hydroxy-3-methoxyphenyl)methylene]hydrazide
  参考文献：
  名称：

  Modulating Magnetic Dynamics of Three Dy₂ Complexes through Keto–Enol Tautomerism of the o-Vanillin Picolinoylhydrazone Ligand

  摘要：

  Complexation of dysprosium(III) with the hetero-donor chelating ligand o-vanillin picolinoylhydrazone (H(2)ovph) in the presence of different bases affords three new dinuclear dysprosium(III) coordination compounds, namely, [Dy-2(ovph)(2)(NO3)(2)(H2O)(2)]center dot 2H(2)O (1), [Dy-2(Hovph) (ovph) (NO3)(2)-(H2O)(4)]center dot NO3 center dot 2CH(3)OH center dot 3H(2)O (2), and Na[Dy-2(Hovph)(2)(mu(2)-OH) (OH)(H2O)(5)]center dot 3Cl center dot 3H(2)O (3), where the aroylhydrazone ligand adopts different coordination modes in respective structures depending on the reaction conditions, as revealed by single-crystal X-ray analyses to be due to their tautomeric maneuver. The magnetic properties of 1-3 are drastically distinct. Compounds 1 and 2 show single-molecule-magnet behavior, while no out alternating current signal is noticed for 3. The structural differences induced by the different coordinate fashions of the ligand may influence the strength of the local crystal field, the magnetic interactions between metal centers, and the local tensor of anisotropy on each Dy site and their relative orientations, therefore generating dissimilar dynamic magnetic behavior.

  DOI：

  10.1021/ic2014978

文献信息

• Solvent-induced single-molecule magnet behavior and near-infrared luminescence properties of rare earth complexes
  作者：Xue-Mei Zhang、Yao-Yao Duan、Hong-Ling Gao、Jian-Zhong Cui

  DOI：10.1039/d0nj03837g

  日期：——

  We synthesized two series of dinuclear rare earth complexes [RE2L2(acac)2(H2O)2]·i-PrOH (RE = Y (1), Eu (2), Dy (3), Ho (4), Er (5) and Yb (6)) and Dy2(L2)2(acac)2(C2H5OH)2 (7) (H2L = pyridine-2-carboxylic acid [(2-hydroxy-3-methoxyphenyl)methylene]hydrazide, Hacac = acetylacetone). The static (dc) magnetic susceptibility shows that the weak ferromagnetic interaction exists in DyIII of 3 and 7. Furthermore

  我们合成了两个系列的双核稀土配合物[RE 2 L 2（acac）2（H 2 O）2 ]·i-PrOH（RE = Y（1），Eu（2），Dy（3），Ho（4），Er（5）和Yb（6））和Dy 2（L 2）2（acac）2（C 2 H 5 OH）2（7）（H 2L ＝吡啶-2-羧酸[（2-羟基-3-甲氧基苯基）亚甲基]酰肼，Hacac ＝乙酰丙酮）。静态（直流）磁化率表明在3和7的Dy III中存在弱的铁磁相互作用。此外，对磁化动力学的研究表明，在零直流磁场下，7具有约45 K的能垒，而在800 Oe直流磁场下，通过溶剂控制的结晶，3的能垒为42.93K。有趣的是，通过降低QTM可以使7的能垒达到80.39K。此外，近红外发光分析表明，该配体可以作为有效的5和6。我们观察到Er III和Yb III离子的特征峰，同时，配合物5在光学系统中具有潜在的应用前景，因为最大峰位于第三个电信窗口中约1531
• Molecular Assembly and Magnetic Dynamics of Two Novel Dy₆ and Dy₈ Aggregates
  作者：Yun-Nan Guo、Xiao-Hua Chen、Shufang Xue、Jinkui Tang

  DOI：10.1021/ic202170z

  日期：2012.4.2

  Complexation of dysprosium(III) with the heterodonor chelating ligand o-vanillin picolinoylhydrazone (H(2)ovph) in the presence of a carbonato ligand affords two novel Dy-6 and Dy-8 clusters, namely, [Dy-6(ovph)(4)(Hpvph)(2)Cl-4 (H2O)(2)(CO3)(2)]center dot CH3OH center dot H2O center dot CH3CN (2) and [Dy-8(ovph)(8)(CO3)(4)(H2O)(8)]center dot 12CH(3)CN center dot 6H(2)O (3). Compound 2 is composed of three petals of the Dy-2 units linked by two carbonato ligands, forming a triangular prism arrangement, while compound 3 possesses an octanuclear core with an unprecedented tub conformation, in which Dy(ovph) fragments are attached to the sides of the carbonato core. The static and dynamic magnetic properties are reported and discussed. In the Dy-6 aggregate, three Dy-2 "skeletons", having been well preserved (see the scheme), contribute to the single-molecule-magnet behavior with a relatively slow tunneling rate, while the Dy-8 cluster only exhibits a rather small relaxation barrier.
• Self-assembly in dinuclear, cyclic homotetranuclear and cyclic heterotetranuclear complexes with a picolylhydrazone ligand
  作者：Dan Wang、Shi-Xiong Liu

  DOI：10.1016/j.poly.2007.08.031

  日期：2007.11

  Reactions among Cu(ClO4)(2) center dot 6H(2)O, Cu(acac)(2)/VO(acac)(2) and 3-methoxysalicylaldehyde Picoloylhydrazone in different solvents give three complexes, [Cu2L(acac)(H2O)(2)]ClO4 (1), [Cu4L2(acac)(2)(py)(2)](ClO4)(2) (2) and (VO2)(2)L2Cu2(acac)(2) (3) (acac = acetyl acetonate and py = pyridine). There is an extended 2D structure in complex I constructed by hydrogen bonds between the binuclear complex cation and the ClO4- anion, and an extended 1D structure in complex 2 constructed by weak pi center dot center dot center dot pi stacking interactions between neighboring cyclic tetranuclear complex molecules. Complex 3 is the first oxovanadium-copper complex with a bridging oxo oxygen atom between the V atom and the Cu atom. The solid-state photoluminescent properties of the three title complexes have been studied. There is an antiferromagnetic interaction in 1. (C) 2007 Elsevier Ltd. All rights reserved.
• Strong Axiality and Ising Exchange Interaction Suppress Zero-Field Tunneling of Magnetization of an Asymmetric Dy₂ Single-Molecule Magnet
  作者：Yun-Nan Guo、Gong-Feng Xu、Wolfgang Wernsdorfer、Liviu Ungur、Yang Guo、Jinkui Tang、Hong-Jie Zhang、Liviu F. Chibotaru、Annie K. Powell

  DOI：10.1021/ja205035g

  日期：2011.8.10

  The high axiality and Ising exchange interaction efficiently suppress quantum tunneling of magnetization of an asymmetric dinuclear Dy-III complex, as revealed by combined experimental and theoretical investigations. Two distinct regimes of blockage of magnetization, one originating from the blockage at individual Dy sites and the other due to the exchange interaction between the sites, are separated for the first time. The latter contribution is found to be crucial, allowing an increase of the relaxation time by 3 orders of magnitude.
• Modulating Magnetic Dynamics of Three Dy₂ Complexes through Keto–Enol Tautomerism of the <i>o</i>-Vanillin Picolinoylhydrazone Ligand
  作者：Yun-Nan Guo、Xiao-Hua Chen、Shufang Xue、Jinkui Tang

  DOI：10.1021/ic2014978

  日期：2011.10.3

  Complexation of dysprosium(III) with the hetero-donor chelating ligand o-vanillin picolinoylhydrazone (H(2)ovph) in the presence of different bases affords three new dinuclear dysprosium(III) coordination compounds, namely, [Dy-2(ovph)(2)(NO3)(2)(H2O)(2)]center dot 2H(2)O (1), [Dy-2(Hovph) (ovph) (NO3)(2)-(H2O)(4)]center dot NO3 center dot 2CH(3)OH center dot 3H(2)O (2), and Na[Dy-2(Hovph)(2)(mu(2)-OH) (OH)(H2O)(5)]center dot 3Cl center dot 3H(2)O (3), where the aroylhydrazone ligand adopts different coordination modes in respective structures depending on the reaction conditions, as revealed by single-crystal X-ray analyses to be due to their tautomeric maneuver. The magnetic properties of 1-3 are drastically distinct. Compounds 1 and 2 show single-molecule-magnet behavior, while no out alternating current signal is noticed for 3. The structural differences induced by the different coordinate fashions of the ligand may influence the strength of the local crystal field, the magnetic interactions between metal centers, and the local tensor of anisotropy on each Dy site and their relative orientations, therefore generating dissimilar dynamic magnetic behavior.