Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 2, Pages 277-283Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901581w
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Funding
- National Science Foundation [CHE-0316623, CHE-0079282]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0809736] Funding Source: National Science Foundation
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Solid-state and solution studies were performed to determine if F- is encapsulated by anion hosts in both media. X-ray crystal structure determinations were compared with both H-1 and F-19 solution NMR data. Three hosts were studied: (1) two polyamide hosts, one with isophthaloyl spacers and the other with pyridine spacers, and (2) a polythioamide host with pyridine spacers. Binding studies showed that the pyridine-containing amide cryptand shows the highest affinity (K-a > 10(5) in DMSO-d(6)), with the other hosts at least a factor of 10 lower. All of the cryptands appear to encapsulate F- in solution, where a deuterium-exchange reaction with DMSO-d(6) can be monitored by F-19 NMR. Four crystal structures are reported and compared: two For the pyridine-containing free base hosts and two for encapsulated F- complexes of the two amide-based cryptands.
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