吡啶氮氧化衍生物与酰胺大环化合物络合性能与结构的关系

doi:10.6023/cjoc201506010

有机化学 ›› 2015, Vol. 35 ›› Issue (11): 2358-2365.DOI: 10.6023/cjoc201506010 上一篇下一篇

研究论文

吡啶氮氧化衍生物与酰胺大环化合物络合性能与结构的关系

陈木娟, 韩淑娟, 廖振华, 黄丹, 李颖, 蒋腊生

华南师范大学化学与环境学院广州 510006

收稿日期:2015-06-09 修回日期:2015-07-02 发布日期:2015-07-10
通讯作者: 蒋腊生 E-mail:jianglsh@scnu.edu.cn
基金资助:
国家自然科学基金(No. 21072066)、广东省省部产学研基金(No. 2012B090700003)和华南师范大学青年教师科研培育基金(No. 14KJ02)资助项目.

Structure-Binding Ability Relationship of Pyridine N-Oxide Derivatives with Diamide-Based Macrocycles

Chen Mujuan, Han Shujuan, Liao Zhenhua, Huang Dan, Li Ying, Jiang Lasheng

School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received:2015-06-09 Revised:2015-07-02 Published:2015-07-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21072066), the Key Project on the Integration of Industry, Education and Research of Guangdong Province (No. 2012B090700003), and the Foundation of Young Teachers of South China Normal University (No.14KJ02).

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摘要/Abstract

介绍了3,5-吡啶二甲酸氮氧衍生物作为客体分子与主体分子酰胺大环的相互作用. 通过质谱和核磁共振氢谱等实验技术研究了吡啶氮氧化物和酰胺大环化合物的结构特点对两者络合作用的影响. 实验结果表明, 3,5-吡啶二甲酰苄胺氮氧化物与酰胺大环化合物的络合能力最强, 3,5-吡啶二甲酰丁胺氮氧化物次之, 3,5-吡啶二甲酸苄酯氮氧化物最弱. 酰胺大环分子的空腔越大其络合吡啶氮氧化物的能力越弱, 酰胺大环上是否含有吡啶环结构对其络合氮氧化物的能力影响较小. 并通过核磁实验进一步验证吡啶酰胺氮氧化合物与酰胺大环形成的[2]准轮烷分子在三氟乙酸/三乙胺的作用下能够发生解离/再组装行为.

关键词: 3,5-吡啶二甲酸氮氧衍生物, 酰胺大环分子, 主客体化学, [2]准轮烷

The 3,5-pyridinedicarboxylic N-oxides derivatives acting as guest molecules were introduced into supramolecular chemistry complexing with the diamide-based macrocycles. The studies on the structure-binding ability relationship of pyridine N-oxides derivatives with diamide-based macrocycles were carried out by ESI-MS, ¹H NMR spectroscopy. The results reveal that the dibenzyl-3,5-pyridinediamine N-oxide shows higher affinity to diamide-based macrocycles than the dibutyl-3, 5-pyridinediamine N-oxide, and the binding ability of dibenzyl-3,5-pyridinedicarboxylate N-oxide is the weakest. The pyridine N-oxide derivatives affinity to the diamide-based macrocycles decreases with increasing size of the cavity of the macrocycles, the diamide-based macrocycle with the pyridine motif reveals weak influence in binding to pyridine N-oxide derivatives. It is also demonstrated that the [2]pseudorotaxane formed by pyridine N-oxide derivatives and diamide-based macrocycles can undergo dethreading/rethreading under the trifluoroacetic acid/triethylamine (TFA/TEA) stimuli.

Key words: 3,5-pyridinedicarboxylic N-oxide derivatives, diamide-based macrocycles, host-guest chemistry, [2]pseudoro- taxanes

引用此文

陈木娟, 韩淑娟, 廖振华, 黄丹, 李颖, 蒋腊生. 吡啶氮氧化衍生物与酰胺大环化合物络合性能与结构的关系[J]. 有机化学, 2015, 35(11): 2358-2365.

Chen Mujuan, Han Shujuan, Liao Zhenhua, Huang Dan, Li Ying, Jiang Lasheng. Structure-Binding Ability Relationship of Pyridine N-Oxide Derivatives with Diamide-Based Macrocycles[J]. Chin. J. Org. Chem., 2015, 35(11): 2358-2365.

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吡啶氮氧化衍生物与酰胺大环化合物络合性能与结构的关系

Structure-Binding Ability Relationship of Pyridine N-Oxide Derivatives with Diamide-Based Macrocycles

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