Application of cup-shaped trilactams for selective extraction of volatile compounds by gas chromatography-mass spectrometry†
*bc
and
Hidehiro
Sakurai
*a
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.
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