Contrasting p K a Shifts in Cucurbit[7]uril Host–Guest Complexes Governed by an Interplay of Hydrophobic Effects and Electrostatic Interactions
2017; American Chemical Society; Volume: 2; Issue: 1 Linguagem: Inglês
10.1021/acsomega.6b00427
ISSN2470-1343
AutoresNuno Basílio, Sandra Gago, A. Jorge Parola, Fernando Piña,
Tópico(s)Molecular Sensors and Ion Detection
ResumoCucurbit[7]uril inclusion complexes with guests bearing dimethylamino groups show the expected upward pKa shifts, whereas their diethylamino counterparts display a decrease in pKa due to the preferential stabilization of the unprotonated form. These results identify the diethylamino group as the substituent of choice to avoid receptor-assisted protonation of guest molecules and present new evidence for the role of the hydrophobic effect as a driving force in cucurbituril complexation.
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