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

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Abstract

Cucurbit[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.

Original languageEnglish
Pages (from-to)70-75
Number of pages6
JournalACS Omega
Volume2
Issue number1
DOIs
Publication statusPublished - 31 Jan 2017

Keywords

  • Calorimetry
  • Enthalpy
  • Entropy
  • Equilibrium constant
  • Free energy
  • Hydrogen
  • Macrocyclic compounds
  • Molecular recognition
  • Spectra

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