含酰亚胺骨架的大环化合物合成、结构及其对阴离子的识别研究
收稿日期: 2013-07-21
修回日期: 2013-09-27
网络出版日期: 2013-10-31
基金资助
国家自然科学基金（No.21061003）和贵州省国际合作基金[No.（2009）700104]资助项目.
Synthesis, Structures of Macrocyclic Compounds Containing Imide Skeleton and the Study on Recognition for F- Ion
Received date: 2013-07-21
Revised date: 2013-09-27
Online published: 2013-10-31
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].
在磷酸催化作用下，采用前体二胺N，N'-（2-胺基苯基）-2，6-二甲酰亚胺吡啶（1）和前体二醛1，4-二（2'-甲酰苯氧基）丁烷（2）进行缩合作用得到[1+1] Schiff碱大环化合物3，进一步将Schiff碱大环3还原得到饱和大环4. 并采用1H NMR，IR，质谱和元素分析等技术对大环3和4的组成进行了表征. 采用X射线单晶衍射技术测定了Schiff碱大环3的晶体结构，结果表明大环 3 具有扭曲的“8”字形结构. 采用UV-vis光谱滴定技术对大环与系列阴离子的键合作用进行了考察，结果表明，Schiff碱大环3对F-离子有明显的选择性识别作用，并测定了该配位反应的配位比和平衡常数.
王芳芳 , 欧敏 , 邓雅欣 , 冉旭 , 张奇龙 , 朱必学 . 含酰亚胺骨架的大环化合物合成、结构及其对阴离子的识别研究[J]. 有机化学, 2014 , 34(2) : 334 -339 . DOI: 10.6023/cjoc201307033
A novel [1+1] Schiff base macrocyclic compound 3 has been synthesized from precursors N,N'-(2-amino- phenyl)pyridine-2,6-dicarboxamide (1) and 1,2-bis(2'-formacylphenoxy)tetrane (2) via condensation in the presence of the phosphoric acid. Furthermore the macrocycle 3 was reduced to the corresponding saturated macrocycle 4. Both macrocycles were characterized by 1H NMR, IR, MS and elemental analysis. The crystal structure of 3 was determined by X-ray diffraction analysis. The result reveals that the macrocycle 3 exhibits twisted to “figure eight” conformation. The results show that the macrocycle 3 displays a selective recognition ability for F- ion by the both macrocycles with a series of anions using UV-vis absorption spectra technique. The stoichiometric ratio and the stability constant of the coordination reaction were determined.
Key words： macrocyclic compound; synthesis; crystal structure; recognition
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