Larger Substituents on Amide Cavitands Induce Bigger Cavities
| Autor: | W. Bernd Schweizer, Ankita Ray, Safwan Aroua, Marc-Olivier Ebert, Andrew N. Lowell, Yoko Yamakoshi, Nils Trapp |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry Adamantane Organic Chemistry Substituent Cavitand Crystal structure 010402 general chemistry 01 natural sciences Biochemistry 3. Good health 0104 chemical sciences chemistry.chemical_compound Crystallography Quinoxaline Intramolecular force Amide Proton NMR Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters, 21 (1) |
| ISSN: | 1523-7052 |
| Popis: | A series of quinoxaline cavitands bearing pendant amide groups with various substituent sizes (Et, iPr, tBu) were synthesized, and their cavity size/structure were investigated by X-ray and NMR analyses. In the case of the Et or iPr amide cavitand, the conformation of the molecule was in the vase form, while the bulky tBu amide cavitand gave the kite conformation at room temperature. X-ray crystal structures of Et and iPr cavitands clearly showed the intramolecular H-bondings to influence the conformation and the cavity sizes dependent on the bulkiness of functional groups. The 1H NMR spectrum revealed that the Et cavitand can encapsulate an adamantane guest compound with slow exchange. |
| Databáze: | OpenAIRE |
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