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Studies of enantiomerization of chiral 3,4‐dihydro‐1,2,4‐benzothiadiazine 1,1‐dioxide type compounds
Author(s) -
Cannazza Giuseppe,
Braghiroli Daniela,
Tait Annalisa,
Baraldi Mario,
Parenti Carlo,
Lindner Wolfgang
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/1520-636x(2001)13:2<94::aid-chir1004>3.0.co;2-o
Subject(s) - chemistry , benzothiadiazine , racemization , enantiomer , reaction rate constant , high performance liquid chromatography , chiral column chromatography , chirality (physics) , chromatography , medicinal chemistry , stereochemistry , kinetics , physics , quantum mechanics , nambu–jona lasinio model , chiral symmetry breaking , quark
An on‐column HPLC procedure using a chiral stationary phase (CSP) was developed for the determination of rate constants and free energy barriers of enantiomerization of (±)IDRA21. Subsequently, the HPLC method was applied for investigation of two structurally related chiral compounds. The individual enantiomers of the studied compounds were isolated in parallel by preparative HPLC and rate constants and free energy barriers of enantiomerization were determined in different solvents. The on‐column enantiomerization data revealed that CSP induces different rate constants for the two enantiomers. The results generated off‐line were used to determine the influence of solvents on the racemization of (+) and (−) IDRA21 and to gain further insight into the enantiomerization mechanism of chiral 3,4‐dihydro‐1,2,4‐benzothiadiazine 1,1‐dioxide type compounds. Chirality 13:94–101, 2001. © 2001 Wiley‐Liss, Inc.