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Liquid chromatographic resolution of cyclic sulfoximides and their sulfoxide precursors on an N,N′‐diallyl‐L‐tartardiamide‐based chiral stationary phase
Author(s) -
Löwendahl A. Christina,
Allenmark Stig G.
Publication year - 1997
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/(sici)1520-636x(1997)9:2<167::aid-chir17>3.0.co;2-l
Subject(s) - chemistry , sulfoxide , elution , dimethyl sulfoxide , chirality (physics) , oxide , resolution (logic) , medicinal chemistry , hydrogen bond , chromatography , organic chemistry , stereochemistry , molecule , computer science , nambu–jona lasinio model , quark , chiral symmetry breaking , physics , quantum mechanics , artificial intelligence
Two O,O′‐diaroyl derivatives of an N,N′‐diallyl‐L‐tartardiamide‐based CSP, 3,5‐dimethylbenzoyl (CSP I) and 4‐tert‐butylbenzoyl (CSP II), have been investigated and compared with respect to retention behaviour and resolving capabilities of a series of endocyclic sulfoximides of the 1‐R‐3‐oxo‐benzo[d]‐isothia (IV)‐azole 1‐oxide type (R = methyl, octyl, 2′‐carboxyphenyl, and 2′‐carbethoxyphenyl) and their corresponding sulfoxide precursors. For the sulfoximides, selectivities of 1.44, 1.27, 1.28, and 1.20, respectively, were found on CSP II when eluted with 15% 2‐propanol in hexane. Both the sulfoximide compounds and their sulfoxide precursors are well resolved by CSPs I and II. The retention was larger on the former phase, indicating that the molecular skeletons of the analytes studied interact, through hydrogen bonding, more strongly with CSP I than CSP II. Chirality 9:167–172, 1997. © 1997 Wiley‐Liss, Inc.