5-hydroxy-N'-[(2-hydroxyphenyl)methylidene]pentanohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-hydroxy-N'-[(2-hydroxyphenyl)methylidene]pentanohydrazide
• 英文别名: 5-hydroxy-N-[(2-hydroxyphenyl)methylidene]pentanohydrazide；5-hydroxy-pentanoic acid (2-hydroxy-benzylidene)-hydrazide；5-hydroxy-pentanoic acid salicylidenehydrazide；H2salhyhp
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: AOFLBEHTYKFLNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-N'-[(2-hydroxyphenyl)methylidene]pentanohydrazide 、 三异丙氧基氧化钒 以 乙醚 为溶剂， 以51%的产率得到[VO₂Hsalhyhp]
  参考文献：
  名称：

  Vanadium complexes with side chain functionalized N-salicylidene hydrazides: Hydrogen-bonding relays as structural directive for supramolecular interactions

  摘要：

  The synthesis and spectroscopic characterization of dioxidovanadium(V) complexes with hydrazone Schiff-base ligands derived from salicylaldehyde and x-hydroxy functionalized carbonic acid hydrazides with three different chain lengths are reported. This includes three series, the ammonium and potassium salts of the complex anions with the twofold deprotonated ligand systems as well as the corresponding neutral complexes [VO2(HL)]. For four complexes within these series crystal structures are reported, namely the full series of complexes with the ligand system containing the shortest chain length (i.e. ammonium salt, potassium salt, and neutral complex) and the ammonium salt with the ligand based on the longest side chain. All complexes posses a dioxidovanadium group with a five-coordinated vanadium atom in a distorted square pyramidal geometry. Within the series of ammonium salts an extensive hydrogen-bonding network including the side chain hydroxyl end group is observed which is virtually independent of the side chain length. Whereas the structure of the potassium salt is governed by ionic contacts resulting in a bilayered packing arrangement with intercalated potassium ions. In the case of the neutral complex a two-dimensional hydrogen-bonding network is observed. Magic angle spinning solid-state V-51 NMR is used to characterize all three series of complexes. The variation of the chemical shift anisotropy parameters is found to be strongly dependent on differences in the supramolecular structure of the compounds, such as hydrogen bonding or crystal packing, which are caused by variation of the protonation state, counterion, and side chain length. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.03.037

文献信息

• Mixed‐Ligand Oxidovanadium(V) Complexes with <i>N′</i> ‐Salicylidenehydrazides: Synthesis, Structure, and ⁵¹ V Solid‐State MAS NMR Investigation
  作者：Simona Nica、Axel Buchholz、Manfred Rudolph、Annika Schweitzer、Maria Wächtler、Hergen Breitzke、Gerd Buntkowsky、Winfried Plass

  DOI：10.1002/ejic.200800063

  日期：2008.5

  The synthesis and spectroscopic characterization of a series of three oxidovanadium(V) complexes with 8-hydroxyquinoline and Schiff-base ligdnds derived from salicylaldehyde and omega-hydroxy-functionalized carbohydrazides with different chain lengths are reported. The complex with the hydrazone ligand containing the shortest chain length was crystallographically characterized. This complex crystallizes

  报道了一系列三种氧化钒 (V) 配合物与 8-羟基喹啉和希夫碱配体的合成和光谱表征，这些配合物来自水杨醛和具有不同链长的 omega-羟基官能化碳酰肼。具有最短链长的腙配体的复合物被结晶学表征。该配合物在三斜空间群 Pi 中结晶，具有两种结构相似但晶体学独立的氧化钒 (V) 配合物。每个钒原子在扭曲的八面体几何形状中是六坐标的。这两个分子是通过侧链取代的席夫碱配体的羟基与两个复合物之一的氧化基之间的氢键相互作用组装的。在乙腈溶液中进行的电化学测量揭示了两个可逆的单电子还原步骤。观察到的第二个还原步骤的前波特征表明存在与 8-羟基喹啉共配体相关的解离平衡。魔角旋转固态 V-51 NMR 光谱允许表征使用的烷基和羟基烷基取代的腙配体的全系列配合物。四极耦合常数很小，约为 4 MHz，在系列内几乎没有变化。化学位移张量的不对称性表明钒 (V) 中心周围的环境相当轴对称。在固态中观察到的各向同性化学位移发生在大约
• Copper(II) Complexes ofω-Hydroxy-FunctionalizedN-Salicylidenehydrazides show pH-Controlled Switching between Dicationic Dimers and Neutral One-Dimensional Coordination Polymers
  作者：Arne Roth、Axel Buchholz、Winfried Plass

  DOI：10.1002/zaac.200600309

  日期：2007.3

  crystallography and represents the first example of a structurally characterized neutral copper(II) N-salicylidenehydrazide complex without additional ligands. The magnetic interactions in the polymers are also antiferromagnetic with J = −125 (1b), −136 (2b), and −148 cm−1 (3b), but strongly reduced compared to the corresponding dimeric complexes. The two basic structure types can be reversibly interconverted

  腙配体 H2salhyhb、H2salhyhp 和 H2salhyhh 的新铜 (II) 配合物已被合成和物理表征，它们源自水杨醛和 ω-羟基碳酸酰肼。根据反应溶液的 pH 值，在固态中发现了两种基本结构。酸性条件导致形成 di-μ-phenoxo-桥接的双阳离子复合物二聚体 [Cu(Hsalhyhb)}2]2+ (1a)、[Cu(Hsalhyhp)}2]2+ (2a) 和 [ Cu(Hsalhyhh)}2]2+ (3a)，以高氯酸盐形式分离。二聚体复合物显示出强反铁磁耦合，J = -399 (1a)、-410 (2a) 和 -311 cm-1 (3a)。较高的 pH 值导致中性铜配体碎片聚集到一维配位聚合物 [Cu(salhyhb)}n] (1b)、[Cu(salhyhp)}n] (2b) 和 [Cu (salhyhh)}n] (3b)。图 3b 已经通过 X 射线晶体学进行了检查，并代表了结构表征的中性铜
• Structural and Catalytic Aspects of Dioxomolybdenum(VI) Complexes with ω-Hydroxy Functionalized<i>N</i>-Salicylidene Hydrazides
  作者：Robert Debel、Axel Buchholz、Winfried Plass

  DOI：10.1002/zaac.200800231

  日期：2008.10

  the side chain by one methylene group in complex 2 leads to a polymeric structure, which is based on a similar intermolecular coordination of the side chain hydroxy group. The further increase of the side-chain length in complex 3 results in the coordination of a methanol molecule at the molybdenum atom. For compounds 2 and 3 the additional hydrogen-bonding network leads to the formation of layered

  新的顺式二氧钼 (VI) 配合物 [MoO2(salhyhb)]2 (1)、[MoO2(salhyhp)] (2) 和 [MoO2(salhyhh)(MeOH)] (3) 与腙配体 H2salhyhb、Hsalhyhp和 H2salhyhh 衍生自水杨醛和具有不同链长的 ω-羟基碳酸酰肼，已被合成和光谱表征。所有三种配合物的晶体结构揭示了具有相同基本结构基序的钼原子的八面体环境。除了两个氧代基团之外，还观察到 [NO3] 供体组，它由三齿席夫碱配体和配位醇的氧原子给出。根据侧链长度观察到不同的缔合模式。对于复合物 1，获得二聚体结构，它通过侧链羟基在另一个单体的钼原子上的配位连接。配合物 2 中一个亚甲基的侧链延伸导致聚合结构，其基于侧链羟基的类似分子间配位。配合物 3 中侧链长度的进一步增加导致甲醇分子在钼原子上的配位。对于化合物 2 和 3，额外的氢键网络导致固态层状结构的形成。测试合成的顺式二氧钼
• Dioxovanadium(v) complexes with side chain substituted N-salicylidenehydrazides modelling supramolecular interactions in vanadium haloperoxidases
  作者：Axel Pohlmann、Simona Nica、T. Kim K. Luong、Winfried Plass

  DOI：10.1016/j.inoche.2004.12.028

  日期：2005.3

  Abstract The water soluble ammonium salts of cis-dioxovanadium( v ) complexes with side chain functionalized N-salicylidenehydrazides show hydrogen bonding interactions relevant for haloperoxidase enzymes. Under turnover conditions for the catalytic bromination of trimethoxybenzene, no substitution of the side chain hydroxy group is observed.

  摘要 顺式-二氧钒( v ) 与侧链功能化的N-水杨酰肼配合物的水溶性铵盐显示出与卤代过氧化物酶相关的氢键相互作用。在三甲氧基苯催化溴化的转换条件下，未观察到侧链羟基的取代。
• Vanadium complexes with side chain functionalized N-salicylidene hydrazides: Hydrogen-bonding relays as structural directive for supramolecular interactions
  作者：Axel Buchholz、Simona Nica、Robert Debel、Annika Fenn、Hergen Breitzke、Gerd Buntkowsky、Winfried Plass

  DOI：10.1016/j.ica.2014.03.037

  日期：2014.8

  The synthesis and spectroscopic characterization of dioxidovanadium(V) complexes with hydrazone Schiff-base ligands derived from salicylaldehyde and x-hydroxy functionalized carbonic acid hydrazides with three different chain lengths are reported. This includes three series, the ammonium and potassium salts of the complex anions with the twofold deprotonated ligand systems as well as the corresponding neutral complexes [VO2(HL)]. For four complexes within these series crystal structures are reported, namely the full series of complexes with the ligand system containing the shortest chain length (i.e. ammonium salt, potassium salt, and neutral complex) and the ammonium salt with the ligand based on the longest side chain. All complexes posses a dioxidovanadium group with a five-coordinated vanadium atom in a distorted square pyramidal geometry. Within the series of ammonium salts an extensive hydrogen-bonding network including the side chain hydroxyl end group is observed which is virtually independent of the side chain length. Whereas the structure of the potassium salt is governed by ionic contacts resulting in a bilayered packing arrangement with intercalated potassium ions. In the case of the neutral complex a two-dimensional hydrogen-bonding network is observed. Magic angle spinning solid-state V-51 NMR is used to characterize all three series of complexes. The variation of the chemical shift anisotropy parameters is found to be strongly dependent on differences in the supramolecular structure of the compounds, such as hydrogen bonding or crystal packing, which are caused by variation of the protonation state, counterion, and side chain length. (C) 2014 Elsevier B.V. All rights reserved.