含硫查尔酮席夫碱及其配合物的合成与表征
摘要
席夫碱及其配合物在立体化学、结构化学、异构现象、磁学、光谱学、动力学和反应机理、配位化学、分析化学、催化、稳定剂、染料和颜料、电光显示以及农业等领域都有着重要作用。肼基二硫代甲酸酯以及缩氨基硫脲衍生的席夫碱及其配合物具有很强的抗癌、抗病毒性能。为此,我们开展了对此类席夫碱及配合物的合成及性质研究。
本文共合成了79个化合物,其中66个是未知化合物,在这66个化合物中,19个已经用单晶衍射确定了具体结构。79个化合物中10个是含硫席夫碱,然后用这十种席夫碱分别与与过渡金属反应得到相应的配合物。最后用元素分析、红外光谱、紫外光谱、核磁共振、摩尔电导率、循环伏安、单晶衍射对这些化合物进行了表征。比较配体和配合物的红外图谱,最明显的是配合物缺少了氮氢吸收峰,说明反应过程中氮上脱去了一个氢原子,而紫外图谱说明了反应后化合物中形成了新的共轭体系。根据核磁图谱的耦合常数表明了配体是一个反式构象。摩尔电导率证明了我们所合成的物质为非电解质。单晶衍射则证明最终化合物的结构。
根据实验最终结果证实了配体是反式构型的双齿配体,在配位时首先发生烯硫醇互变,然后脱去一个氢,最后硫原子和亚胺中的氮原子与金属原子发生配位。
The Schiff bases and their complexs are very important in stereochemistry, configuration chemistry, magnetics, spectroscopy, dynamics, and reaction mechanism, coordination chemistry, analytical chemistry, catalysis, coloring matter, the area of agriculture, and so on. The Schiff bases from S-methyldithiocarbazate and thiosemicarbazide, including their complexes, have strongly antitumour and antivirus activities.
In this paper seventy nine compounds have been reported, in which sixty six of them are unknown componds, and nineteen structures of them have been confirmed by the X-Ray diffraction method. There are ten sulfuric Schiff bases in the seventy compounds. These ten sulfuric Schiff bases were used to comlexation with transition metal ions. All of Schiff bases and their complexes were characterized by elemental analysis, IR spectra, UV spectra, 1H NMR, molar conductance, cyclic voltammetry and X-ray diffraction. Compared with the ligand from the IR spectra, it is obvious that the complexes run short of the N-H band, which is confirmed that a hydrogen atom deviate from the nitrogen atom in the reaction progress. The UV spectra indicate that a new conjunction system have formed in the reaction. According to the coupling constant of the 1H NMR, it is show that the ligands are the trans isomer. The molar conductance and X-Ray diffraction confirmed that these complexes are nonelectrolytes and the structures of the compounds.
The experimental results have shown that these Schiff bases appear to be a bidentate ligand with trans configuration to coordinate the metal through the azomethine nitrogen and thioenolic sulfur atom.
本文共合成了79个化合物,其中66个是未知化合物,在这66个化合物中,19个已经用单晶衍射确定了具体结构。79个化合物中10个是含硫席夫碱,然后用这十种席夫碱分别与与过渡金属反应得到相应的配合物。最后用元素分析、红外光谱、紫外光谱、核磁共振、摩尔电导率、循环伏安、单晶衍射对这些化合物进行了表征。比较配体和配合物的红外图谱,最明显的是配合物缺少了氮氢吸收峰,说明反应过程中氮上脱去了一个氢原子,而紫外图谱说明了反应后化合物中形成了新的共轭体系。根据核磁图谱的耦合常数表明了配体是一个反式构象。摩尔电导率证明了我们所合成的物质为非电解质。单晶衍射则证明最终化合物的结构。
根据实验最终结果证实了配体是反式构型的双齿配体,在配位时首先发生烯硫醇互变,然后脱去一个氢,最后硫原子和亚胺中的氮原子与金属原子发生配位。
The Schiff bases and their complexs are very important in stereochemistry, configuration chemistry, magnetics, spectroscopy, dynamics, and reaction mechanism, coordination chemistry, analytical chemistry, catalysis, coloring matter, the area of agriculture, and so on. The Schiff bases from S-methyldithiocarbazate and thiosemicarbazide, including their complexes, have strongly antitumour and antivirus activities.
In this paper seventy nine compounds have been reported, in which sixty six of them are unknown componds, and nineteen structures of them have been confirmed by the X-Ray diffraction method. There are ten sulfuric Schiff bases in the seventy compounds. These ten sulfuric Schiff bases were used to comlexation with transition metal ions. All of Schiff bases and their complexes were characterized by elemental analysis, IR spectra, UV spectra, 1H NMR, molar conductance, cyclic voltammetry and X-ray diffraction. Compared with the ligand from the IR spectra, it is obvious that the complexes run short of the N-H band, which is confirmed that a hydrogen atom deviate from the nitrogen atom in the reaction progress. The UV spectra indicate that a new conjunction system have formed in the reaction. According to the coupling constant of the 1H NMR, it is show that the ligands are the trans isomer. The molar conductance and X-Ray diffraction confirmed that these complexes are nonelectrolytes and the structures of the compounds.
The experimental results have shown that these Schiff bases appear to be a bidentate ligand with trans configuration to coordinate the metal through the azomethine nitrogen and thioenolic sulfur atom.
引文
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4. G. S. Huang, Y. H. Liu, B. H. Chen, and Y. X. Ma, (E)-cinnamoylferrocene S-Benzylcarbo- dithioylhydrazone and its chelates, Chem. Papers., 1999, 53(1), 65.
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