Comparative Enantioseparation of Crufomate with Cellulose- and Amylose-based Chiral Stationary Phases on Reverse-Phase and Normal-Phase High-Performance Liquid Chromatography

Abstract

This study used cellulose-and amylose-based chiral stationary phases to comparatively separate crufomate enantiomers on reverse-phase and normal-phase high performance liquid chromatography (RP-HPLC and NP-HPLC). The baseline separations were obtained on Phenomene Lux cellulose-1, Lux cellulose-2 and Lux amylose-2 with 2-propanol/hexane and on Lux cellulose-1 and Lux amylose-2 with acetonitrile/water as mobile phase. The results of optical rotation detections showed that (+)-enantiomer of crufomate was firstly eluted on Lux cellulose-1 and Lux amylose-2 both on NP-HPLC and RP-HPLC, while the (-)-enantiomer was firstly eluted on Lux cellulose-2 and Lux cellulose-3 on NP-HPLC. The influences of column temperature from 5-40 ºC on separation were investigated on three chiral stationary phases. The thermodynamic parameters were calculated using van't Hoff equations to study the enthalpy-driven and entropy-driven process. This work will be helpful to prepare optical pure enantiomers and establish efficient analytical method for study on enantioselective behaviours of crufomate.

Direct Enantioseparation of Nitrogen‐Heterocyclic Pesticides on Cellulose‐Based Chiral Column by High‐Performance Liquid Chromatography

“…Generally, Lux Cellulose-3 with a substituted group of 4-methylbenzoate on cellulose-based chiral stationary showed better chiral discriminability for bitertanol (1), fenbuconazole (3), imazalil (5), and carfentrazone-ethyl (8) than Lux Cellulose-2 with 3chloro-4-methylphenylcarbamate. Additionally, charge transfer π-π interactions between the CSP and the aromatic rings of the racemates can also provide stabilization of the solute-CSP complexes 20 . The differences of the substituted groups on cellulose-based chiral stationary might result in the change of enantiomer-CSP interactions and recognition mechanisms.…”

“…In the enantiomer-CSP interactions and recognition mechanisms, enantiomers with different stereochemistries were inserted into chiral grooves of CSPs in the process of solute-CSP complexes formation, and then enantioseparation on CSPs occurs, 19 OH groups on chiral centers are available to participate in hydrogen bonding with the C = O group of the CSP. Additionally, charge transfer π-π interactions between the CSP and the aromatic rings of the racemates can also provide stabilization of the solute-CSP complexes 20 .…”

Simultaneous stereoselective detection of chiral fungicides in soil by LC-MS/MS with fast sample preparation

“…A Phenomenex Lux Cellulose‐2 column (250 mm × 4.6 mm, 5 μm) was used for enantioseparation, packed with a CSP of CCMPC . The stereoselective separation was carried out in a mixture of water (A) and acetonitrile (B) as the mobile phase.…”