| Abstract
| - Equilibrium gas-phase acidities of the six isomeric cyclohexanediols were measured in a Fouriertransform ion cyclotron resonance mass spectrometer. Although all six cyclohexanediols have the samefunctional groups and similar structures, the acidities vary over 11 kcal/mol. This large difference is duemostly to the balance between hydrogen bonding and geometric strain. To understand the origins of theacidity differences in more detail, the conformations and energetics of the cyclohexanediols were studiedusing density functional theory, which gave good agreement with the experimental acidities. Finally,methanol−methoxide and methanol−methanol interactions were used as a model for the hydrogen bonding.
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