Enantiomerization of an inherently chiral resorcarene derivative: determination of the interconversion barrier by computer simulation of the dynamic HPLC experiment

Abstract

The inherently chiral tetrabenzoxazine resorcarene derivative 1 shows characteristic plateau-formation during enantioselective HPLC separation on the chiral stationary phase Chiralpak AD. By computer assisted peak form analysis of the elution profiles, obtained from temperature dependent dynamic HPLC (DHPLC) experiments, with ChromWin, the enantiomerization barrier Δ G #(298 K)=92±2 kJ mol −1 and the activation parameters Δ H #=53.0±1.8 kJ mol −1 and Δ S #=−131±14 J (K mol) −1 were determined.