Rate constant determination of interconverting enantiomers by chiral chromatography using a stochastic model

Sepsey, Annamária; Németh, Dóra Rita; Németh, Gábor; Felinger, Attila

doi:10.1016/j.chroma.2018.06.014

Cited by 10 publications

(4 citation statements)

References 45 publications

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“…In both cases, the lack of an obvious plateau between adjacent peaks corresponding to enantiomers (i.e. "batman peak" indicative of on-column enantiomer interconversion) 84 is consistent with atropisomeric stability. Assuming that ΔS for bond rotations is expected to be small, 85 ΔG is expected to vary little with temperature, so that, on a first approximation, the ΔG obtained can be compared to computed values discussed later.…”

Section: Scheme 2 Proposed Syntheses Of 15-disubstituted 123-triazole...mentioning

confidence: 63%

Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

et al. 2022

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The synthesis and characterisation of axially chiral atropisomeric 1,5-disubstituted 1,2,3triazoles is reported. Molecules designed to display restricted rotation about 1,2,3-triazole N-1-aryl or 1,2,3-triazole C-5-aryl bonds were investigated by physical and computational techniques. The barrier to 1,2,3-triazole N-1-aryl rotation was found to be higher than that for 1,2,3-triazole C-5-aryl rotation, confirming axial chirality stemming from restricted rotation about an N-1-aryl bond in a 1,5-disubstituted 1,2,3-triazole to be the most suitable for the development of an axial chirality triazole-based platform.

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Section: Scheme 2 Proposed Syntheses Of 15-disubstituted 123-triazole...mentioning

confidence: 63%

Enantiomer stability of atropisomeric 1,5-disubstituted 1,2,3-triazoles

et al. 2022

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“…The situation in ion mobility spectrometry is very similar to that in dynamic electrophoresis and dynamic chromatography. [82][83][84][85][86][87][88] If interconversion takes place on a time-scale significantly faster than the time-scale of the separation, the peaks that would correspond to the separate conformers/isomers will merge into a single feature with no additional broadening. 89,90 Fast-interconverting ions will drift with a velocity that is the weighted average of the drift velocities of the individual conformers/isomers.…”

Section: Total Peak Broadening and The Plate-height Equation In Ion Mmentioning

confidence: 99%

Plate-height model of ion mobility-mass spectrometry

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Kirk

et al. 2020

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“…Can both ideal and nonideal adsorption kinetics be observed for an enantiopure analyte that is studied under conditions that cause interconversion? 75 Single-molecule spectroscopy could quantify the heterogeneous nano-to microscale lengths relevant to the stationary phase in chiral chromatography. Commonly used cellulosebased stationary phases contain chirality on hierarchal length scales: from the Angstrom level of individual monomer cellulose sugars (Figure 4B) to the polymerization of chiral chains (Figure 4C) and finally the self-assembly of chains into supramolecular chiral fibrils on nano-, micro-, and even macrolength scales (Figure 4D).…”

Section: ■ Studying Complex Single-molecule Samples More Relevant To ...mentioning

confidence: 99%

“…By monitoring >10 5 individual interactions, what is the percent contribution of the different ideal, nonideal, and nonstereoselective kinetic populations? Can both ideal and nonideal adsorption kinetics be observed for an enantiopure analyte that is studied under conditions that cause interconversion?…”

Section: Chiral Chromatographyexpanding the Types Of Separations Stu...mentioning

confidence: 99%