Influence of the protonation state on the binding mode of methyl orange with cucurbiturils

被引：20
作者：
He, Suhang [1 ]
Sun, Xuzhuo [2 ]
Zhang, Haibo [1 ]
机构：
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
[2] Henan Univ Technol, Coll Chem & Chem Engn, Zhengzhou 450001, Peoples R China
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2016年 / 1107卷
基金：
中国国家自然科学基金;
关键词：
Cucurbituril; Methyl orange; Crystal structure; Complexation; INCLUSION; COMPLEXES; CYCLODEXTRIN; GUEST; HOSTS;
D O I：
10.1016/j.molstruc.2015.11.039
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Binding modes of methyl orange (MO) with cucurbiturils (CBs) have been investigated by Single Crystal X-ray Diffraction and NMR Spectroscopy. Detailed study of intermolecular interactions was supported by the Hirshfeld surface analysis. Protonation state of the anionic part of methyl orange has greatly influenced the binding mode of the complex. Stabilized by hydrogen bonding at the portal, hydrophobic and dispersion interactions in the cavity, the protonated methyl orange was deeply inserted into the cavity. On the contrary, the anionic methyl orange has been pushed towards the outside of the cavity by the electrostatic repulsion between the azo group and the portal oxygen. A "water bridge" was found in MO@CB8 linking both host and guest via hydrogen bonds. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码：182 / 188
页数：7
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