Cucurbit[7]uril-Modulated H/D Exchange of α-Carbonyl Hydrogen: Deceleration in Alkali and Acceleration in Acid Conditions
| Autor: | Weiquan Xu, Yang Jiao, Bohan Tang, Jiang-Fei Xu, Xi Zhang |
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| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Langmuir. 38:541-546 |
| ISSN: | 1520-5827 0743-7463 |
| Popis: | Supramolecular catalysis based on host-guest interactions has aroused much attention in past decades. Among the various strategies, modulation of the reactivity of key intermediates is an effective strategy to achieve high-efficiency supramolecular catalysis. Here, we report that by utilizing the host-guest interaction of cucurbit[7]uril (CB[7]), the reactivity of anionic enolate and cationic oxonium, the intermediates of H/D exchange of the α-carbonyl hydrogen in alkali and acid conditions, respectively, could be modulated effectively. On one hand, in alkaline conditions, both the electrostatic effect and the steric hindrance effect of CB[7] disfavored formation of the enolate anion intermediate. On the other hand, in acidic conditions, the oxonium was stabilized and the solvent effect was weakened by the electrostatic effect of CB[7]. As a result, the H/D exchange of 1-(4-acetylphenyl) |
| Databáze: | OpenAIRE |
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