Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups
We report the synthesis and characterization of a new acyclic cucurbit[n]uril (CB[n]) host C1 that features four alkyl sulfate ionic groups. The X-ray crystal structure of the C1·Me6CHDA complex is reported. Host C1 is significantly less soluble in water (4 mM) compared to the analogous acyclic CB[n...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2025-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.21.55 |
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| Summary: | We report the synthesis and characterization of a new acyclic cucurbit[n]uril (CB[n]) host C1 that features four alkyl sulfate ionic groups. The X-ray crystal structure of the C1·Me6CHDA complex is reported. Host C1 is significantly less soluble in water (4 mM) compared to the analogous acyclic CB[n] host M1 which features sulfonate ionic groups (346 mM). Host C1 does not undergo significant self-association according to the results of 1H NMR dilution experiments. The molecular recognition behavior of the hosts C1 and M1 toward a panel of seven ammonium ions was explored by 1H NMR spectroscopy and isothermal titration calorimetry (ITC). We find that C1 generally binds slightly more tightly than M1 toward a specific guest. C1 binds more tightly to quaternary ammonium guests compared to the corresponding primary ammonium ions. |
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| ISSN: | 1860-5397 |