Terminal Carboxylate Effects on the Thermodynamics and Kinetics of Cucurbit[7]uril Binding to Guests Containing a Central Bis(Pyridinium)-Xylylene Site

A series of bis­(pyridinium)-xylylene derivatives bearing carboxylate terminal groups were investigated as guests for the cucurbit­[7]­uril host in aqueous solution. While the presence of the terminal carboxylates has a modest effect on the thermodynamic stability of the complexes, the kinetics of c...

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Veröffentlicht in:Journal of organic chemistry 2019-02, Vol.84 (4), p.2325-2329
Hauptverfasser: Neira, Iago, García, Marcos D, Peinador, Carlos, Kaifer, Angel E
Format: Artikel
Sprache:eng
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Zusammenfassung:A series of bis­(pyridinium)-xylylene derivatives bearing carboxylate terminal groups were investigated as guests for the cucurbit­[7]­uril host in aqueous solution. While the presence of the terminal carboxylates has a modest effect on the thermodynamic stability of the complexes, the kinetics of complex association/​​dissociation is strongly affected. The relative position (meta, para) of the carboxylate group in relation to the pyridinium nitrogen also exerts a considerable effect on the binding kinetics.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02993