Contrasting pK _a Shifts in Cucurbit[7]uril Host-Guest Complexes Governed by an Interplay of Hydrophobic Effects and Electrostatic Interactions.

ABSTRACT: Cucurbit[7]uril inclusion complexes with guests bearing dimethylamino groups show the expected upward pK _a shifts, whereas their diethylamino counterparts display a decrease in pK _a 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.

SUBMITTER: Basilio N 

PROVIDER: S-EPMC6640924 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature