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2013 , Vol. 33 >Issue 02: 325 - 331

DOI: https://doi.org/10.6023/cjoc201210010

研究论文

新型[1+1] Schiff碱大环化合物的合成与表征

  • 胡鹏 ,
  • 郭思颖 ,
  • 张奇龙 ,
  • 张云黔 ,
  • 朱必学
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  • a 贵州大学大环及超分子化学重点实验室 贵阳 550025;
    b 贵阳医学院化学教研室 贵阳 550004

收稿日期: 2012-10-09

  修回日期: 2012-11-03

  网络出版日期: 2012-11-15

基金资助

国家自然科学基金(No. 21061003);贵州省国际合作(No. (2009)700104)资助项目.

收起

Synthesis, Characterization of Novel [1+1] Schiff Base Macrocyclic Compounds

  • Hu Peng ,
  • Guo Siying ,
  • Zhang Qilong ,
  • Zhang Yunqian ,
  • Zhu Bixue
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  • a Key Laboratory of Macrocyclic and Supramolecular Chemistry, Guizhou University, Guiyang 550025;
    b Department of Chemistry, Guiyang Medical College, Guiyang 550004

Received date: 2012-10-09

  Revised date: 2012-11-03

  Online published: 2012-11-15

Supported by

Project supported by the National Natural Science Foundation of China (No.21061003) and the International Cooperation Foundation of Guizhou Province [No. (2009)700104].

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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.

关键词： Schiff碱; 大环化合物; 合成; 晶体结构

本文引用格式

胡鹏 , 郭思颖 , 张奇龙 , 张云黔 , 朱必学 . 新型[1+1] Schiff碱大环化合物的合成与表征[J]. 有机化学, 2013 , 33(02) : 325 -331 . DOI: 10.6023/cjoc201210010

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)-1,4,7- trioxaheptane] 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

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