Tuning CH Hydrogen Bond-Based Receptors toward Picomolar Anion Affinity via the Inductive Effect of Distant Substituents
Status PubMed-not-MEDLINE Language English Country Germany Media print-electronic
Document type Journal Article
Grant support
23-05271S
Grantová Agentura České Republiky
LM2018121
Ministerstvo Školství, Mládeže a Tělovýchovy
CZ.02.1.01/ 0.0/0.0/17_043/0009632
Ministerstvo Školství, Mládeže a Tělovýchovy
LM2018127
Ministerstvo Školství, Mládeže a Tělovýchovy
LM2023052
Ministerstvo Školství, Mládeže a Tělovýchovy
857560
Horizon 2020
- Keywords
- Anion Binding, Bambusurils, Host−Guest Chemistry, Macrocycles, NMR Spectroscopy,
- Publication type
- Journal Article MeSH
Inspired by nature, artificial hydrogen bond-based anion receptors have been developed to achieve high anion selectivity; however, their binding affinity is usually low. The potency of these receptors is usually increased by the introduction of aryl substituents, which withdraw electrons from their binding site through the resonance effect. Here, we show that the polarization of the C(sp3 )-H binding site of bambusuril receptors, and thus their potency to bind anions, can be modulated by the inductive effect. The presence of electron-withdrawing groups on benzyl substituents of bambusurils significantly increases their binding affinities to halides, resulting in the strongest iodide receptor reported to date with an association constant greater than 1013 M-1 in acetonitrile. A Hammett plot showed that while the bambusuril affinity toward halides linearly increases with the electron-withdrawing power of their substituents, their binding selectivity remains essentially unchanged.
Department of Chemistry Faculty of Science Masaryk University 625 00 Brno Czech Republic
RECETOX Faculty of Science Masaryk University 625 00 Brno Czech Republic
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A Bambusuril Receptor Binds Charge Diffuse Anions in Water at Picomolar Concentrations
Substituent effects of fluorinated bambusurils on their anion transport
