Collect. Czech. Chem. Commun. 1979, 44, 410-419

Infrared spectra and conformation of substituted methyl cyclohexanecarboxylates and 2-hydroxycyclohexanecarboxylates

Soňa Vašíčková and Miloš Tichý

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Infrared bands due to carbonyl and hydroxyl stretching vibration were measured for 32 esters of substituted cyclohexane and trans-decalin carboxylic acids and 2-hydroxy acids. The bands were computer-separated and most of them assigned to the appropriate rotamers. The conformational equilibrium in methyl trans-2-hydroxy-cis-4-isopropylcyclohexanecarboxylate was determined using comparison of integrated intensities of the hydroxyl bands of the mobile compound with those of the conformationally biased standards. The OH/COOCH3 vicinal interaction was found to be attractive (about 2.6 kJ mol-1).