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

doi:10.6023/cjoc201506010

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (11): 2358-2365.DOI: 10.6023/cjoc201506010 Previous Articles Next Articles

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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

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).

1. Structure-Binding Ability Relationship of Pyridine N-Oxide Derivatives with Diamide-Based Macrocycles.PDF(1822KB)

Abstract

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

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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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