Epimer distinction and structural effects on gas-phase acidities of alcohols measured using the kinetic method

Epimers of methylcyclohexanol are distinguished by their relative gas-phase acidities (ΔG o acid ) obtained by a method which is based on the relative rates of competitive fragmentations of cluster ions. The estimated ΔG o acid values for cis-2-methylcyclohexanol, trans-2-methylcyclohexanol, cis-4-methylcyclohexanol, and trans-4-methylcyclohexanol are 364.1±0.1, 365.1±0.1, 365.1±0.1, and 366.2±0.1 kcal/mol, respectively