Experimental (NMR) and theoretical (MD simulations) studies on the conformational preference of three cycloalkanols when included in β-cyclodextrin

Mariluz Zubiaur, Miguel De Federico, Kepa K. Burusco, Ivan Beá, Albert Virgili, Francisco Sánchez-Ferrando, Carlos Jaime

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4 Citations (Scopus)

Abstract

The inclusion complexes between three cycloalkanols (cyclopentanol, cyclohexanol and cycloheptanol) and β-cyclodextrin (β-CD) have been studied by NMR experiments, and by molecular dynamics (MD) simulations. Complexes present medium to small association constants. All experimental data show the equatorial conformer as the most stable after complexation because no changes were detected in the coupling constants of the H1 protons. Intermolecular ROE experiments suggest that while cyclopentanol is deeply included into the β-CD cavity, cyclohexanol and cycloheptanol occupy mainly the wider entrance. The MD simulations agree with the experimental data (equatorial conformers are always the most stable), and average geometries coincide with those deduced from the ROE experiments. © Springer 2005.
Original languageEnglish
Pages (from-to)241-247
JournalJournal of Inclusion Phenomena and Molecular Recognition in Chemistry
Volume51
Issue number3-4
DOIs
Publication statusPublished - 1 Apr 2005

Keywords

  • β-cyclodextrin
  • Cycloalkanols
  • Host-guest chemistry
  • Inclusion complexes
  • Molecular dynamics

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