Work

Investigation of Self-Disproportionation of Enantiomers via Column Chromatography (SDEvCC) Using 3-(ortho-Substituted-phenyl)quinazolin-4-one Derivatives

Year: 2026

Type: article

Abstract: In this study, the applicability of achiral column chromatography—including both medium-pressure liquid chromatography (MPLC) and classical gravity-driven techniques—was evaluated as a laboratory method for enantiomeric enrichment of scalemic (non-racemic) samples of axially chiral compounds. As model substrates, 3-(ortho-substituted-phenyl)quinazolin-4-one derivatives were employed. The results confirmed that self-disproportionation of enantiomers (SDE), occurring during column chromatography (SDEvCC), enabled the efficient isolation of enantiomerically pure fractions, with MPLC demonstrating particularly high effectiveness. Additionally, the parameters governing gravity-driven column chromatography were systematically optimized, with particular attention to variables such as eluent type and concentration, stationary phase composition, sample preparation protocol, and solvent purity. Furthermore, leveraging known crystallographic data and quantum chemical calculations based on Density Functional Theory (DFT), a molecular association mechanism was proposed to elucidate the physicochemical basis of the SDE phenomenon.

Source: Symmetry

DOI: 10.3390/sym18040699

Authors: Tomomi Imai, Shumpei Terada, Osamu Kitagawa, Magdalena Kwiatkowska, Alicja Wzorek, Vadim A. Soloshonok

Institutions: Shibaura Institute of Technology, Jan Kochanowski University, Ikerbasque, University of the Basque Country

Language: English

Topic: Analytical Chemistry and Chromatography

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $2,896

Funder: Ministerstwo Edukacji i Nauki