Journal of Computer-Aided Molecular Design

, Volume 28, Issue 4, pp 319–325 | Cite as

Binding of cyclic carboxylates to octa-acid deep-cavity cavitand

  • Corinne L. D. Gibb
  • Bruce C. Gibb


As part of the fourth statistical assessment of modeling of proteins and ligands ( prediction challenge, the strength of association of nine guests (19) binding to octa-acid host was determined by a combination of 1H NMR and isothermal titration calorimetry. Association constants in sodium tetraborate buffered (pH 9.2) aqueous solution ranged from 5.39 × 102 M−1 in the case of benzoate 1, up to 3.82 × 105 M−1 for trans-4-methylcyclohexanoate 7. Overall, the free energy difference between the free energies of complexation of these weakest and strongest binding guests was ΔΔG° = 3.88 kcal mol−1. Based on a multitude of previous studies, the anticipated order of strength of binding was close to that which was actually obtained. However, the binding of guest 3 (4-ethylbenzoate) was considerably stronger than initially estimated.


Supramolecular chemistry Host-guest chemistry Water Hydrophobic effect 



The authors acknowledge the financial support of the National Institutes of Health (GM098141) in carrying out this research.


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Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  1. 1.Department of ChemistryTulane UniversityNew OrleansUSA

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