Abstract
The gas-phase equilibria of diastereomers have been investigated in a flow system. The following reactions have been studied: (1), threo to- erythro form of 3-methylpentanol-2; (2), cis-to- trans form of 2-, 3-, and 4-methylcyclohexanol; (3), menthol-to-neomenthol; and (4), borneol-to-isoborneol. The values of ΔH r o and ΔS r o for (1) and (2) were calculated from the temperature dependence of the equilibrium constants making use of the least-squares method. The values of ΔG r o(503 K) for transformations (3) and (4) were also determined. It was shown that the enthalpy changes of the reactions increase in the alcohol series: acyclic-to-cyclic-to-bicyclic and this evidently is accounted for by the decrease of degrees of freedom of internal rotation. The determined dependence can be of a great importance for the development of additive schemes for calculating ΔH f o for cyclic compounds.
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