Chinese Journal of Organic Chemistry >
Synthesis, Structure and Anion Recognition of Urea-Functionalized Schiff Base Macrocyclic Compound
Received date: 2016-05-28
Revised date: 2016-09-02
Online published: 2016-10-08
Supported by
Project supported by the National Natural Science Foundation of China (No. 21061003), and the ‘Chun-Hui’ Fund of Ministry of Education (No. Z2012054).
A novel [1+1] Schiff base macrocyclic compound 3 has been synthesized from the reaction of precursors 1,3-bis(3-amino-phenyl)-urea (1) with 1,3-bis(2-formylphenoxy)-2-propa-nol (2). The macrocycle 3 was characterized by 1H NMR, FT-IR, FABMS spectra and elemental analysis, and the crystal structure of 3 was determined by X-ray diffraction analy-sis. The results show that the macrocycle 3 displays a selective recognition ability for AcO- ion by the coordination reaction of 3 with a series of anions using UV-vis absorption spectra technique. Furthermore, the coordination reaction of 3 with AcO- ion was investigated via UV-Vis spectra, 1H NMR and the isothermal titration calorimeter (ITC) respectively. The stoichiometric ratio, the association constant (K) and the thermodynamic parameters (ΔrHm, ΔrSm and ΔrGm) of the coordination reaction were obtained.
Key words： Schiff base macrocycle; crystal structure; Urea; AcO-; recognition
Zhang Wenlong , Chen Dongmei , Liu Xingli , Huang Chao , Zhu Bixue . Synthesis, Structure and Anion Recognition of Urea-Functionalized Schiff Base Macrocyclic Compound[J]. Chinese Journal of Organic Chemistry, 2017 , 37(2) : 474 -479 . DOI: 10.6023/cjoc201605042
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