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

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.