Vibrational circular dichroism in hydrogen bond systems: Part II. Vibrational circular dichroism of the OH stretching vibration in 2,2-dimethyl-1,3-dioxolane-4-methanol

Abstract

Vibrational circular dichroism (VCD) of the OH stretching band in 2,2-dimethyl-1,3- dioxolane-4-methanol has been studied. The OH stretching vibration for the intramolecularly hydrogen-bonded species in the (R)-enantiomer gives rise to a positive VCD band but no VCD band for the hydrogen-bond free species. It is shown that the G −G + conformation in the intramolecular hydrogen bond system ▪ gives a positive VCD band for the OH stretching vibration. The thermodynamic parameters in equilibrium between the free and intramolecularly hydrogen-bonded species have been determined as Δ H =−7.8 kJ mol −1 and Δ S = −18 kJ K −1 mol −1.