Experimental and computational investigations on the high binding-selectivity of pyrimidine derivatives by a pillar[5]arene |
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| Authors: | Qian Zhang Ke-Qing Li Jun-Hui Yang Gui-Rong Qu Na-Na Ma Hai-Ming Guo |
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| Affiliation: | 1. Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Chinazhangqian1980@163.com mann076@htu.edu.cn guohm518@hotmail.com;3. Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, China |
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| Abstract: | The binding selectivity of an adenine-monofunctionalized pillar[5]arene (H) with a series of pyrimidine derivatives were investigated through 1H NMR experiments and density functional theory (DFT) study. High binding-selectivity was demonstrated. Typically, H displayed very strong binding strength with 6-(2,4-dioxo-3, 4-dihydropyrimidin-1 (2H)-yl)hexanenitrile (G1) [Ka >105 M?1], up to about 3000-fold as compared with 1-hexylpyrimidine-2,4(1H, 3H)-dione (G5) [Ka = 31 M?1]. The strong binding ability of H with G1 was due to the cooperative multiple hydrogen bond, dipole-dipole, C-H···π and π···π interactions. The high binding-selectivity was also verified by calculation results. The calculated interaction energy (ΔEi) of G1?H was ?12.92 Kcal·mol?1 while that of G5?H was ?2.85 Kcal·mol?1. |
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| Keywords: | Pillar[5]arene binding-selectivity density functional theory (DFT) cooperative interactions |
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