In previous studies, Okamoto et al. described the results of the exceptionally large chiral recognitionof 2-(benzylsulfinyl)benzamide onto a coated-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate). As a continuation and deepening of those studies, here the sulfoxide and asmall set of its structural analogues were analyzed on the commercially available Chiralpak IC-3 chiralstationary phase based upon the same polysaccharide derivative as the chiral selector but immobilizedonto silica support.The chromatographic results obtained using different mobile phases consisting of pure methanol,ethanol and 2-propanol or binary mixtures n-hexane-2-propanol, which are prohibited with the pro-genitor coated-type chromatographic support, permitted to identify the NH2of the amide group as thekey structural element of the (S)-enantiomer of 2-(benzylsulfinyl)benzamide for obtaining a very highaffinity for the IC-3 chiral stationary phase.

A chromatographic study on the exceptional chiral recognition of 2-(benzylsulfinyl)benzamide by animmobilized-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate) / Carradori, Simone; Secci, Daniela; Faggi, Cristina; Cirilli, Roberto. - In: JOURNAL OF CHROMATOGRAPHY A. - ISSN 0021-9673. - STAMPA. - 1531:(2018), pp. 151-156. [10.1016/j.chroma.2017.11.037]

A chromatographic study on the exceptional chiral recognition of 2-(benzylsulfinyl)benzamide by animmobilized-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate)

Daniela Secci;
2018

Abstract

In previous studies, Okamoto et al. described the results of the exceptionally large chiral recognitionof 2-(benzylsulfinyl)benzamide onto a coated-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate). As a continuation and deepening of those studies, here the sulfoxide and asmall set of its structural analogues were analyzed on the commercially available Chiralpak IC-3 chiralstationary phase based upon the same polysaccharide derivative as the chiral selector but immobilizedonto silica support.The chromatographic results obtained using different mobile phases consisting of pure methanol,ethanol and 2-propanol or binary mixtures n-hexane-2-propanol, which are prohibited with the pro-genitor coated-type chromatographic support, permitted to identify the NH2of the amide group as thekey structural element of the (S)-enantiomer of 2-(benzylsulfinyl)benzamide for obtaining a very highaffinity for the IC-3 chiral stationary phase.
2018
2-(Benzylsulfinyl)benzamide; high enantioselectivity; enantiomers; chiralpak IC-3; absolute configuration; H-bonding
01 Pubblicazione su rivista::01a Articolo in rivista
A chromatographic study on the exceptional chiral recognition of 2-(benzylsulfinyl)benzamide by animmobilized-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate) / Carradori, Simone; Secci, Daniela; Faggi, Cristina; Cirilli, Roberto. - In: JOURNAL OF CHROMATOGRAPHY A. - ISSN 0021-9673. - STAMPA. - 1531:(2018), pp. 151-156. [10.1016/j.chroma.2017.11.037]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1020963
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