Chelate effect in cyclodextrin dimers: A computational (MD, MM/PBSA, and MM/GBSA) study

Ivan Beà, Martin G. Gotsev, Petko M. Ivanov, Carlos Jaime, Peter A. Kollman

Research output: Contribution to journalArticleResearchpeer-review

31 Citations (Scopus)

Abstract

The complexation of an adamantyl-phosphate derivative with one β-cyclodextrin, with two β-cyclodextrins, and with two β-cyclodextrins dimerized with a disulfide bridge was studied by computational methods (MD, MM/PBSA, and MM/GBSA) to analyze and rationalize the chelate effect. Although this effect is usually explained by invoking favorable entropy contribution due to the preorganization of the ligand, it has been determined experimentally that in this case it is enthalpy-driven. The computational results are in accord with this finding, although the entropy contribution due to the solvent structural organization around the complex is crucial for the final estimates of the free energy of complexation. © 2006 American Chemical Society.
Original languageEnglish
Pages (from-to)2056-2063
JournalJournal of Organic Chemistry
Volume71
Issue number5
DOIs
Publication statusPublished - 5 Mar 2006

Fingerprint Dive into the research topics of 'Chelate effect in cyclodextrin dimers: A computational (MD, MM/PBSA, and MM/GBSA) study'. Together they form a unique fingerprint.

  • Cite this

    Beà, I., Gotsev, M. G., Ivanov, P. M., Jaime, C., & Kollman, P. A. (2006). Chelate effect in cyclodextrin dimers: A computational (MD, MM/PBSA, and MM/GBSA) study. Journal of Organic Chemistry, 71(5), 2056-2063. https://doi.org/10.1021/jo052469o