Complexation of two macrocycles for amide, saccharide, and halide derivatives: the capacity of 1,2,3-triazole as hydrogen and halogen bonding acceptors
作者:Dong-Yun Wang、Li-Yan You、Ji-Liang Wang、Hui Wang、Dan-Wei Zhang、Zhan-Ting Li
DOI:10.1016/j.tetlet.2013.10.064
日期:2013.12
Two 1,2,3-triazole- and amide-incorporated macrocycles have been prepared by 1,3-dipolar cycloaddition of the corresponding dialkyne and diazide precursors. Intramolecular C-H center dot center dot center dot O hydrogen bonding is introduced to lock the C-5-H atoms of the 1,2,3-triazole rings. The binding of the two macrocycles to amide, monosaccharide, and halide derivatives in chloroform or dichloromethane has been investigated. It is revealed that the amide units dominate their binding toward the amide and monosaccharide guests through forming intermolecular hydrogen bonding and 1,2,3-triazole is as weak as an intermolecular hydrogen bonding acceptor, but it forms intermolecular halogen bonding when cooperative effect exists. (C) 2013 Elsevier Ltd. All rights reserved.