Synthesis of 2,6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO-

doi:10.6023/cjoc201705016

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 2911-2918.DOI: 10.6023/cjoc201705016 Previous Articles Next Articles

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含2,6-吡啶二甲酰胺基和二甲基双吡咯甲烷单元的大环合成及其与醋酸根的键合性质

刘兴丽, 汤正河, 陈冬梅, 张文龙, 陈怀育, 朱纯, 朱必学

贵州大学大环及超分子化学重点实验室贵阳 550025

收稿日期:2017-05-09 修回日期:2017-07-11 发布日期:2017-08-30
通讯作者: 朱必学 E-mail:bxzhu@gzu.edu.cn
基金资助:
国家自然科学基金（No.21663008）、教育部春晖计划（Nos.Z2012054，Z2016009）及贵州大学研究生创新基金（No.2017004）资助项目.

Synthesis of 2,6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO^-

Liu Xingli, Tang Zhenghe, Chen Dongmei, Zhang Wenlong Chen Huaiyu, Zhu Chun, Zhu Bixue

Key Laboratory of Macrocyclic and Supramolecular Chemistry, Guizhou University, Guiyang 550025

Received:2017-05-09 Revised:2017-07-11 Published:2017-08-30
Contact: 10.6023/cjoc201705016 E-mail:bxzhu@gzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21663008), the "Chun-Hui" Fund of Ministry of Education (Nos. Z2012054, Z2016009) and the Graduate Student Innovative Funding of Guizhou University (No. 2017004).

1. Synthesis of 2,6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO^-.PDF(1601KB)

Abstract

[1+1] Schiff base macrocycle 3 has been synthesized from the reaction of precursors N,N'-bis(3-aminophenyl)-pyridine-2,6-dicarboxamide (1) with 5,5-dimethyl-1,9-diformyldipyrromethane (2), and furthermore the macrocycle 3 was reduced to the corresponding saturated macrocycle 4. The two macrocycles were characterized by ¹H NMR, FT-IR, FABMS spectroscopies and elemental analysis, and the crystal structure of 4 was determined by X-ray diffraction analysis. Properties of the two macrocycles hydrogen-bonding interactions with AcO^- were investigated using UV-Vis, ¹H NMR, the isothermal titration calorimeter (ITC), as well as density functional theory (DFT) calculations. The stoichiometric ratio, binding constant (K) and the thermodynamic parameters (Δ_rH_m, Δ_rS_m and Δ_rG_m) of binding interactions were obtained. The results demonstrate that the macrocycle 3 binds AcO^- with a 1:1 binding stoichiometry (K_a≈10⁵ L·mol^-1), and the more flexible macrocyclic receptor 4 binds AcO^- with a 1:2 binding stoichiometry (K_a1≈10³ L·mol^-1, K_a2≈10⁵ L·mol^-1).

Key words: 2,6-diamidopyridine, dipyrromethane, macrocycle, AcO^-, hydrogen bond

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Liu Xingli, Tang Zhenghe, Chen Dongmei, Zhang Wenlong Chen Huaiyu, Zhu Chun, Zhu Bixue. Synthesis of 2,6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO^-[J]. Chin. J. Org. Chem., 2017, 37(11): 2911-2918.

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含2,6-吡啶二甲酰胺基和二甲基双吡咯甲烷单元的大环合成及其与醋酸根的键合性质

Synthesis of 2,6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO^-

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