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新型[1+1]Schiff碱大环化合物的合成与表征
Synthesis, Characterization of Novel [1+1] Schiff Base Macrocyclic Compounds
【摘要】 在硫酸催化作用下,采用前体二醛1,7-二(2’-甲酰苯基)-4-氮-1,7-二氧-4-(4’-对甲苯磺酸基)庚烷(1)和1,7-二(2’-甲酰苯基)-1,4,7三氧庚烷(2)与二胺化合物N,N’-(2-胺基苯基)-2,6-二甲酰亚胺吡啶(3)分别进行缩合,得到[1+1]Schiff碱大环化合物4和5,并用元素分析、1H NMR、IR和质谱等对大环化合物4和5进行表征.同时用X射线衍射方法测定了2个前体和2个Schiff碱大环的晶体结构.单晶X射线衍射结果表明,2个大环化合物分子中,分子内氢键作用导致整个分子呈现为一扭曲"8"字形构型,分子内一对苯环之间的π-π相互作用进一步稳定其分子的扭曲结构.其紫外研究结果显示,大环化合物4和5对镧(III)离子具有选择性识别作用.
【Abstract】 Two novel [1+1] Schiff base macrocyclic compounds 4 and 5 have been synthesized from Precursor 1 [1,7-bis(2’-formylphenyl)-4-aza-1,7-dioxa-4-(4’-toluenesulfonyl)heptane] and Precursor 2 [1,7-bis(2’-formylphenyl)-1,4,7trioxaheptane] with diamine 3 [N,N’-(2-aminophenyl)pyridine-2,6-dicarboxamide] via condensation and cyclizaction in acid-catalyzed condition,respectively,and the structures were characterized by elemental analysis,1H NMR,IR and MS techniques.Simultaneously,the crystal structures of two compounds 4 and 5 were determined by X-ray diffraction analysis.The X-ray single crystal analysis reveals that each of the two macrocycles 4 and 5 exhibits twisted "figure eight" conformation due to the strong intramolecular hydrogen bonding interactions,and the stabilized structure in part by the intramolecular π-π stacking interactions between the two benzene rings.The studies on the UV-vis absorption spectra show that the two macrocycles 4 and 5 have a selective recognition for La3+ ion.
【Key words】 Schiff base; macrocyclic compound; synthesis; crystal structure;
- 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2013年02期
- 【分类号】O621.3
- 【被引频次】17
- 【下载频次】457