Chinese Journal of Organic Chemistry >
Synthesis of 2,6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO-
Received date: 2017-05-09
Revised date: 2017-07-11
Online published: 2017-08-30
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+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 (ΔrHm, ΔrSm and ΔrGm) of binding interactions were obtained. The results demonstrate that the macrocycle 3 binds AcO- with a 1:1 binding stoichiometry (Ka≈105 L·mol-1), and the more flexible macrocyclic receptor 4 binds AcO- with a 1:2 binding stoichiometry (Ka1≈103 L·mol-1, Ka2≈105 L·mol-1).
Key words： 2,6-diamidopyridine; dipyrromethane; macrocycle; AcO-; hydrogen bond
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]. Chinese Journal of Organic Chemistry, 2017 , 37(11) : 2911 -2918 . DOI: 10.6023/cjoc201705016
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