| Autor: |
Goodwin RJ; Research School of Chemistry, Australian National University, Canberra, ACT, Australia. michelle.coote@anu.edu.au nicholas.white@anu.edu.au., Blyth MT, Fung AKK, Smith LM, Norcott PL, Tanovic S, Coote ML, White NG |
| Jazyk: |
angličtina |
| Zdroj: |
Organic & biomolecular chemistry [Org Biomol Chem] 2021 Mar 28; Vol. 19 (12), pp. 2794-2803. Date of Electronic Publication: 2021 Mar 15. |
| DOI: |
10.1039/d1ob00282a |
| Abstrakt: |
Hydroxypyridinium and hydroxyquinolinium compounds containing acidic O-H groups attached to a cationic aromatic scaffold were synthesized, i.e. N-methyl-3-hydroxypyridinium (1 + ) and N-methyl-8-hydroxyquinolinium (2 + ). These very simple compounds are capable of binding to chloride very strongly in CD 3 CN and with moderate strength in 9 : 1 CD 3 CN : D 2 O. Comparison with known association constants reveals that 1 + and 2 + bind chloride in CD 3 CN or CD 3 CN : D 2 O with comparable affinities to receptors containing significantly more hydrogen bond donors and/or higher positive charges. Crystal structures of both compounds with coordinating anions were obtained, and feature short O-Hanion hydrogen bonds. A receptor containing two hydroxyquinolinium groups was also prepared. While the low solubility of this compound caused difficulties, we were able to demonstrate chloride binding in a competitive 1 : 1 CD 3 CN : CD 3 OD solvent mixture. Addition of sulfate to this compound results in the formation of a crystallographically-characterised solid state anion coordination polymer. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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