High-performance liquid chromatography enantioseparation of chiral 2-(benzylsulfinyl)benzamide derivatives on cellulose tris(3,5-dichlorophenylcarbamate) chiral stationary phase

Simone Carradori, Daniela Secci, Paolo Guglielmi, Marco Pierini, Roberto Cirilli

Research output: Contribution to journalArticlepeer-review

Abstract

Recently it has been reported that immobilized chlorinated-type chiral stationary phases based on cellulose tris(3,5-dichlorophenylcarbamate) are able to express an outstanding enantioselectivity towards the structure of 2-(benzylsulfinyl)benzamide. We now introduce two homologue series of chiral sulfoxides based on the same 2-(sulfinyl)benzoyl core as the prototype of new selectands for HPLC, whose enantioselectivity could be modulable through the replacement of the benzyl group with an unbranched alkyl chain varying in length from 1 to 5 carbon atoms. HPLC parameters such as mobile phase composition and column temperature have been carefully evaluated in order to get pertinent structure-enantioselectivity relationships. The enantiomer elution order was unambiguously determined by a combined strategy involving theoretical and experimental procedures. Two cases of temperature-dependent inversion of the elution order of enantiomers in the operative temperature range of chiral chromatographic support were observed.

Original languageEnglish
Pages (from-to)460572
JournalJournal of Chromatography A
Volume1610
DOIs
Publication statusPublished - Jan 11 2020

Keywords

  • Benzamides/chemistry
  • Cellulose/analogs & derivatives
  • Chromatography, High Pressure Liquid/methods
  • Entropy
  • Phenylcarbamates/chemistry
  • Stereoisomerism
  • Sulfoxides/chemistry
  • Temperature

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