Citation: Manuel Petroselli, Yong-Qing Chen, Ming-Kai Zhao, Julius Rebek, Yang Yu. C-H···X-C bonds in alkyl halides drive reverse selectivities in confined spaces[J]. Chinese Chemical Letters, ;2023, 34(5): 107834. doi: 10.1016/j.cclet.2022.107834 shu

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

Manuel Petroselli ^a ,
Yong-Qing Chen ^a ,
Ming-Kai Zhao ^a ,
Julius Rebek ^{a, b} ,
Yang Yu ^{a, *,}

a.
Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, China
b.
Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, United States

yangyu2017@shu.edu.cn

Received Date: 28 June 2022
Revised Date: 8 September 2022
Accepted Date: 14 September 2022
Available Online: 18 September 2022

Figures(5)

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.
- Water-soluble cavitand,
- Host-guest complex,
- Molecular recognition,
- C-H hydrogen bond,
- Alkyl halides
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