Application of cup-shaped trilactams for selective extraction of volatile compounds by gas chromatography-mass spectrometry?

Analyst Pub Date: 2020-07-24 DOI: 10.1039/D0AN01061H

Abstract

Chiral cyclic trilactams ((+)-1 and (?)-1) with C3 symmetry were investigated as liquid phase extraction materials of volatile compounds. Perfume samples, involving a range of chiral odor active terpenoids, were applied and each sample before and after the liquid phase extraction was analyzed by solid phase microextraction (SPME)-gas chromatography hyphenated with mass spectrometry. It was found that (+)-1 exhibited significantly higher enrichment factors for several terpenoids, while (?)-1 did not. The mode of interactions between each enantiomer and L-menthol and Kharismal (methyl dihydrojasmonate) was further investigated by molecular dynamics (MD) simulations and theoretical density functional theory (DFT) calculations, showing the favorable interactions of enriched substrates with (+)-1 through noncovalent interactions, either hydrogen bonds or electrostatic interactions.

Graphical abstract: Application of cup-shaped trilactams for selective extraction of volatile compounds by gas chromatography-mass spectrometry
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