Chinese Journal of Organic Chemistry >
Structure-Binding Ability Relationship of Pyridine N-Oxide Derivatives with Diamide-Based Macrocycles
Received date: 2015-06-09
Revised date: 2015-07-02
Online 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).
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.
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]. Chinese Journal of Organic Chemistry, 2015 , 35(11) : 2358 -2365 . DOI: 10.6023/cjoc201506010
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