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

Simone Carradori, Daniela Secci, Cristina Faggi, Roberto Cirilli

Research output: Contribution to journalArticle

Abstract

In previous studies, Okamoto et al. described the results of the exceptionally large chiral recognition of 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 a small set of its structural analogues were analyzed on the commercially available Chiralpak IC-3 chiral stationary phase based upon the same polysaccharide derivative as the chiral selector but immobilized onto 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 progenitor coated-type chromatographic support, permitted to identify the NH2 of the amide group as the key structural element of the (S)-enantiomer of 2-(benzylsulfinyl)benzamide for obtaining a very high affinity for the IC-3 chiral stationary phase.

Original languageEnglish
Pages (from-to)151-156
Number of pages6
JournalJournal of Chromatography A
Volume1531
DOIs
Publication statusPublished - Jan 5 2018

Fingerprint

sulfoxide
2-Propanol
Enantiomers
Binary mixtures
Amides
Silicon Dioxide
Polysaccharides
Methanol
Ethanol
Derivatives
benzamide
cellulose tris(3,5-dichlorophenylcarbamate)
Haemophilus influenzae type b-polysaccharide vaccine-diphtheria toxoid conjugate
n-hexane

Keywords

  • Benzamides/analysis
  • Cellulose/analogs & derivatives
  • Chromatography, High Pressure Liquid/methods
  • Crystallography, X-Ray
  • Molecular Conformation
  • Phenylcarbamates/chemistry
  • Polysaccharides/chemistry
  • Solvents/chemistry
  • Stereoisomerism
  • Sulfoxides/chemistry
  • Thermodynamics

Cite this

@article{9276c71140e14f68ad977e8971a08ee9,
title = "A chromatographic study on the exceptional chiral recognition of 2-(benzylsulfinyl)benzamide by an immobilized-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate)",
abstract = "In previous studies, Okamoto et al. described the results of the exceptionally large chiral recognition of 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 a small set of its structural analogues were analyzed on the commercially available Chiralpak IC-3 chiral stationary phase based upon the same polysaccharide derivative as the chiral selector but immobilized onto 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 progenitor coated-type chromatographic support, permitted to identify the NH2 of the amide group as the key structural element of the (S)-enantiomer of 2-(benzylsulfinyl)benzamide for obtaining a very high affinity for the IC-3 chiral stationary phase.",
keywords = "Benzamides/analysis, Cellulose/analogs & derivatives, Chromatography, High Pressure Liquid/methods, Crystallography, X-Ray, Molecular Conformation, Phenylcarbamates/chemistry, Polysaccharides/chemistry, Solvents/chemistry, Stereoisomerism, Sulfoxides/chemistry, Thermodynamics",
author = "Simone Carradori and Daniela Secci and Cristina Faggi and Roberto Cirilli",
note = "Copyright {\circledC} 2017 Elsevier B.V. All rights reserved.",
year = "2018",
month = "1",
day = "5",
doi = "10.1016/j.chroma.2017.11.037",
language = "English",
volume = "1531",
pages = "151--156",
journal = "Journal of Chromatography A",
issn = "0021-9673",
publisher = "Elsevier",

}

TY - JOUR

T1 - A chromatographic study on the exceptional chiral recognition of 2-(benzylsulfinyl)benzamide by an immobilized-type chiral stationary phase based on cellulose tris(3,5-dichlorophenylcarbamate)

AU - Carradori, Simone

AU - Secci, Daniela

AU - Faggi, Cristina

AU - Cirilli, Roberto

N1 - Copyright © 2017 Elsevier B.V. All rights reserved.

PY - 2018/1/5

Y1 - 2018/1/5

N2 - In previous studies, Okamoto et al. described the results of the exceptionally large chiral recognition of 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 a small set of its structural analogues were analyzed on the commercially available Chiralpak IC-3 chiral stationary phase based upon the same polysaccharide derivative as the chiral selector but immobilized onto 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 progenitor coated-type chromatographic support, permitted to identify the NH2 of the amide group as the key structural element of the (S)-enantiomer of 2-(benzylsulfinyl)benzamide for obtaining a very high affinity for the IC-3 chiral stationary phase.

AB - In previous studies, Okamoto et al. described the results of the exceptionally large chiral recognition of 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 a small set of its structural analogues were analyzed on the commercially available Chiralpak IC-3 chiral stationary phase based upon the same polysaccharide derivative as the chiral selector but immobilized onto 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 progenitor coated-type chromatographic support, permitted to identify the NH2 of the amide group as the key structural element of the (S)-enantiomer of 2-(benzylsulfinyl)benzamide for obtaining a very high affinity for the IC-3 chiral stationary phase.

KW - Benzamides/analysis

KW - Cellulose/analogs & derivatives

KW - Chromatography, High Pressure Liquid/methods

KW - Crystallography, X-Ray

KW - Molecular Conformation

KW - Phenylcarbamates/chemistry

KW - Polysaccharides/chemistry

KW - Solvents/chemistry

KW - Stereoisomerism

KW - Sulfoxides/chemistry

KW - Thermodynamics

U2 - 10.1016/j.chroma.2017.11.037

DO - 10.1016/j.chroma.2017.11.037

M3 - Article

C2 - 29174571

VL - 1531

SP - 151

EP - 156

JO - Journal of Chromatography A

JF - Journal of Chromatography A

SN - 0021-9673

ER -