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

The inherently chiral tetrabenzoxazine resorearene derivative I 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 DeltaG(#)(298 K) = 92 +/-2 kJ mol(-1) and the activation parameters DeltaH(#) = 53.0 +/-1.8 kJ mol(-1) and DeltaS(#) = -131 +/-4 J (K mol)(-1) were determined. (C) 2001 Elsevier Science Ltd. All rights reserved.