1996
DOI: 10.1021/ja960050x
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NMR Studies of Chiral Discrimination Relevant to the Liquid Chromatographic Enantioseparation by a Cellulose Phenylcarbamate Derivative

Abstract: Chromatographic enantioseparation of 1,1‘-bi-2-naphthol (2) and its mono- and di-O-methylated derivatives (3a, 3b), 2,2‘-dihydroxy-6,6‘-dimethylbiphenyl (4), and 10,10‘-dihydroxy-9,9‘-biphenanthryl (5) has been performed on cellulose tris(5-fluoro-2-methylphenylcarbamate) (1) as a chiral stationary phase for high-performance liquid chromatography (HPLC). The complete base-line separation of 2 and 4 was achieved with the elution order of enantiomers such that the (R)-isomers eluted first followed by the (S)-iso… Show more

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Cited by 196 publications
(165 citation statements)
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References 70 publications
(67 reference statements)
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“…Okamoto's group developed a series of CSPs based on cellulose trisphenylcarbamate derivatives (CTPCs) adsorbed to macroporous silica [109]. The chiral recognition mechanism on CTPC phases was elucidated by X-ray analysis, NMR studies [110,111] and computer simulations [38]. CTPC has a left-handed 3/2 helical conformation and the glucose residues are regularly arranged along the helical axis.…”
Section: Direct Methodsmentioning
confidence: 99%
“…Okamoto's group developed a series of CSPs based on cellulose trisphenylcarbamate derivatives (CTPCs) adsorbed to macroporous silica [109]. The chiral recognition mechanism on CTPC phases was elucidated by X-ray analysis, NMR studies [110,111] and computer simulations [38]. CTPC has a left-handed 3/2 helical conformation and the glucose residues are regularly arranged along the helical axis.…”
Section: Direct Methodsmentioning
confidence: 99%
“…A chiral helical channel is formed along the backbone. Aromatic moieties are located at the surface of the chain while the polar groups are located in the interior [180]. The shape of the chiral cavities varies depending on the nature of the substitution on the polysaccharide [125].…”
Section: Mixed Types Of Interactionsmentioning
confidence: 99%
“…52 The chiral recognition mechanism of these CSPs has been studied by NMR and computer simulation. 53,54 Industrial-scale preparative separation has already started with the simulated moving-bed system, which is suitable for the separation of two components. 55,56 Our CSPs are used for these separations.…”
Section: Development Of Chiral Stationary Phases (Csps) For High-perfmentioning
confidence: 99%