Work

Design, Synthesis, and Applications of Bis‐Amido HPLC Pirkle‐Type Chiral Stationary Phases

Year: 2024

Type: article

Abstract: ABSTRACT Two different types of chiral stationary phases, based on Pirkle's design, were created by attaching chiral selectors to 3‐mercapto silica gel. To prepare the enantiomeric selectors, 3,5‐dinitrobenzoyl and naphthyl groups were sequentially added to a chiral 1,2‐diaminocyclohexane core. The chiral selectors demonstrated enantioselectivity towards ibuprofen enantiomers in solution, as confirmed by 1H NMR spectroscopy, and in initial HPLC testing, the enantiomeric selectors showed enantioselectivity for selected racemic solutes (viz., α = 1.27 for1,1′‐bi‐(2‐naphthol)). Molecular docking studies revealed that the chiral selectors had a bent structure and a cleft‐like cavity where the analyte could be held during complexation while establishing H‐bonding and π–π stacking interactions.

Source: Chirality

DOI: 10.1002/chir.23715

Authors: Maria Aurora Guarducci, Simone Manetto, Marco Pierini, Giulia Mazzoccanti, Claudio Villani

Institution: Sapienza University of Rome

Language: English

Topic: Analytical Chemistry and Chromatography

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,840

Funder: Sapienza Università di Roma