C-H…X-C bonds in alkyl halides drive reverse selectivities in confined spaces  

作　　者：Manuel Petroselli Yong-Qing Chen Ming-Kai Zhao Julius Rebek Jr. Yang Yu 

机构地区：[1]Center for Supramolecular Chemistry and Catalysis and Department of Chemistry,College of Science,Shanghai University,Shanghai 200444,China [2]Skaggs Institute for Chemical Biology and Department of Chemistry,The Scripps Research Institute,La Jolla,CA 92037,United States

出　　处：《Chinese Chemical Letters》2023年第5期237-240,共4页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.22071144 and 21801164);Shanghai Scientific and Technological Committee(No.22010500300);the Program for Professor of Special Appointment(Dongfang Scholaship)of the Shanghai Education Committee。

摘　　要：Binding of non-activated alkyl halides(2-20)in water-soluble cavitand(1)through supramolecular forces is here reported,with emphasis on the role of size and polarizability of the halogen atom in the formation of intramolecular C-H hydrogen bonds in confined spaces.Rare reverse affinity in water(RI<RBr<RCl)is surprisingly observed for the more water-soluble short alkyl halides in dynamic open-ended containers.Competitive bindings and theoretical calculations confirm the unusual selectivity and the presence of C-H hydrogen bonds in non-activated systems for the first time,pointing out the importance and effect of subtle forces on molecular recognition in confined spaces.

关 键 词：Water-soluble cavitand Host-guest complex Molecular recognition C-H hydrogen bond Alkyl halides 

分 类 号：O641.3[理学—物理化学]