Separation of non-racemic mixtures of enantiomers by achiral chromatography

Olbrycht, Maksymilian; Gumieniak, Justyna; Mruc, Patrycja; Balawejder, Maciej; Piątkowski, Wojciech; Antos, Dorota

doi:10.1016/j.chroma.2023.463877

Cited by 5 publications

(2 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Notably, an observable SDE arising from the preferential 2D chiral-based association packing of chiral compounds adsorbed on achiral surfaces has never been demonstrated. It is also worth noting that Olbrycht has argued strongly that the SDE in liquid chromatography is determined almost exclusively by the formation of homo-and heterochiral associates on already adsorbed molecules rather than the formation of homo-and heterochiral associates in the bulk liquid phase [7]. [35][36][37][38] as a possible explanation for the SDEvE, SDE via adsorptive bubble separation (SDEvABS), and SDEvGC of scalemic α-pinene (3).…”

Section: Sde Via Evaporation (Sdeve)mentioning

confidence: 99%

“…The self-disproportionation of enantiomers (SDE) phenomenon [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] occurs whenever any physicochemical process is used to fractionate a scalemic sample (an unequal mixture of two enantiomers of a compound) resulting in an uneven distribution of the enantiomers across the fractions due to molecular associations yielding differential formation of homo-and heterochiral associates [1][2][3][4]. The SDE manifests itself in all manner of physicochemical processes, the most well-known being recrystallization, and also includes processes involving the gaseous phase, such as sublimation [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The Self-Disproportionation of Enantiomers (SDE) of α-Pinene via Evaporation off Silica Gel and Foam Fractionation—Validation of the Plausibility of SDE via Gas Chromatography (GC) for α-Pinene

2023

View full text Add to dashboard Cite

α-Pinene is an intriguing monoterpene as it has been reported to undergo the self-disproportionation of enantiomers (SDE) phenomenon via gas chromatography (GC), the only compound to decisively demonstrate this. Examples of the SDE involving the gaseous phase—sublimation aside—are extremely rare. Attempts to replicate the GC results were unsuccessful, though the authors argued convincingly for the difficulty of observing the phenomenon. However, we could effect for α-pinene SDE via evaporation off silica gel and by foam fractionation—albeit the SDE magnitude for both was only very slight—to confirm that α-pinene can undergo the SDE for processes involving a gaseous phase and thus validate the plausibility of the GC report. The indications are that the molecular associations responsible for the various SDE observations of α-pinene occur not in the gaseous phase or the bulk phase but rather in two-dimensional (2D) adsorbed monolayers and are not based on conventional functional group-based intermolecular interactions and instead are, most likely, as a result of homo- and heterochiral packing differences in the 2D monolayers—a well-known 2D chiral-based association packing effect. These are also the first reports of the occurrence of the SDE using an adsorptive bubble separation process (foam fractionation) and involving a gaseous phase other than sublimation, GC, and distillation.

show abstract