Gas chromatographic determination of the interconversion energy barrier for dimethyl-2,3-pentadienedioate enantiomers

The enantiomers of dimethyl-2,3-pentadienedioate undergo interconversion during gas chromatographic separation on 2,6-di-O-methyl-3-O-pentyl-beta-, 2,6-di-O-methyl-3-O-pentyl-gamma-, and 2,3-di-O-methyl-6-O-tert butyldimethylsilyl-beta-CD chiral stationary phases. The combination of a deconvolution method with an internal standard was used to determine individual enantiomer peak areas and retention times needed for the calculation of the interconversion rate constants and the energy barrier for dimethyl-2,3-pentadienedioate enantiomers. The kinetic and thermodynamic data obtained for the interconversion data (rate constants, energy barriers, enthalpies, and entropies) were in good agreement with the published data (Trapp, O., Schurig, V., Chirality 2002, 14, 465-470) using permethylated-beta-CD (Chirasil-beta-Dex).