Carbonyl Groups as Molecular Valves to Regulate Chloride Binding to Squaramides
| Autor: | Rajeev S. Muthyala, Seogjoo Jang, Maciej E. Domaradzki, Vijayakumar Ramalingam |
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| Rok vydání: | 2008 |
| Předmět: |
Hydrogen bond
Chemistry Organic Chemistry Squaramide Photochemistry Amides Biochemistry Chloride Ion Channels Ion Chlorides Biomimetic Materials Chloride Channels Intramolecular force Polymer chemistry Chloride channel medicine Physical and Theoretical Chemistry Anion binding Cyclobutanes Ion channel medicine.drug |
| Zdroj: | Organic Letters. 10:3315-3318 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol801204s |
| Popis: | Environment-sensitive binding of anions to synthetic receptors is important for the functional mimicry of ion channels. We describe new squaramide-based chloride ion receptors whose anion binding cavity can be opened and closed by using carbonyl groups as valves. In nonpolar solvents, the carbonyls preclude chloride binding via intramolecular hydrogen bonding with the squaramide NHs. In polar solvents, disruption of the intramolecular hydrogen bonds reorients the carbonyl groups and opens the anion-binding cavity. |
| Databáze: | OpenAIRE |
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