Issue 8, 1999

Enantiomerization kinetics studied by dynamic enantioselective liquid chromatography: Solvent, temperature and stationary phase effects on the rate of N-benzyl-1,3,2-benzodithiazole 1-oxide enantiomer interconversion

Abstract

Enantiomerization of 1 was found to proceed ca. 10 times faster in hexane than in methanol. This has been attributed to the difference in ΔS found in the respective solvents. The presence of a chiral HPLC stationary phase (Whelk-O1) did not affect the rate of enantiomerization to any significant extent. The previously determined enantiomerization (by inversion of configuration) barrier of 2 using DHPLC (80 kJ mol–1), is thus considered correct, and not biased by the presence of the stationary phase.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1999, 1587-1590

Enantiomerization kinetics studied by dynamic enantioselective liquid chromatography: Solvent, temperature and stationary phase effects on the rate of N-benzyl-1,3,2-benzodithiazole 1-oxide enantiomer interconversion

J. Oxelbark and S. Allenmark, J. Chem. Soc., Perkin Trans. 2, 1999, 1587 DOI: 10.1039/A904649F

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