Effect of Hydrogen Binding on Selective Recognition of Halide Anions  

作　　者：Juan Du Kang Kang Jinchuan Hu Lijun Mao Lihua Yuan Wen Feng 

机构地区：[1]Institute of Nuclear Science and Technology, Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, China

出　　处：《Chinese Journal of Chemistry》2016年第9期866-872,共7页中国化学（英文版）

摘　　要：The interplay of molecular rigidity enforced by interior or exterior hydrogen bonding and affinity for binding halide anions is described to demonstrate the effect of intramolecular hydrogen bonding in anion recognition process. To this end pyridine-2,6-dicarboxamides 1 and 2, and aromatic oligoamides 3 and 4 containing intramolecular hydrogen bonds were explored for their ability in associating with tetrabutylammonium halide （Cl^-, Br^-, and I^-）. Binding constants in chloroform solution were calculated using nonlinear curve-fitting method based on ^1H NMR titration experiments. The trimeric amide 3, which adopts a crescent conformation as revealed by single-crystal X-ray diffraction analysis, strongly binds chloride anion with binding constant as high as 379 L·mol^-1. This is more than 6 times greater than the binding constant for the control receptor 2 with a backbone that is only partially rigidifled. The comparative data provided supportive information for rationalizing the observed affinity difference in binding halide anions in terms of local preorganization effected by interior or exterior hydrogen bonding.The interplay of molecular rigidity enforced by interior or exterior hydrogen bonding and affinity for binding halide anions is described to demonstrate the effect of intramolecular hydrogen bonding in anion recognition process. To this end pyridine-2,6-dicarboxamides 1 and 2, and aromatic oligoamides 3 and 4 containing intramolecular hydrogen bonds were explored for their ability in associating with tetrabutylammonium halide （Cl^-, Br^-, and I^-）. Binding constants in chloroform solution were calculated using nonlinear curve-fitting method based on ^1H NMR titration experiments. The trimeric amide 3, which adopts a crescent conformation as revealed by single-crystal X-ray diffraction analysis, strongly binds chloride anion with binding constant as high as 379 L·mol^-1. This is more than 6 times greater than the binding constant for the control receptor 2 with a backbone that is only partially rigidifled. The comparative data provided supportive information for rationalizing the observed affinity difference in binding halide anions in terms of local preorganization effected by interior or exterior hydrogen bonding.

关 键 词：hydrogen bonding halide anion recognition SELECTIVITY 

分 类 号：O[理学]