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

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
12
Issue
10
Identifiers
DOI: 10.1016/s0957-4166(01)00246-4

Abstract

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.

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