Literature DB >> 16642493

Fast and precise access to enantiomerization rate constants in dynamic chromatography.

O Trapp1.   

Abstract

An analytical solution of the unified equation to evaluate elution profiles of interconverting enantiomers in dynamic chromatography is presented. Rate constants k1 and k(-1) and Gibbs activation energies are directly obtained from the chromatographic parameters (retention times tR A and tR A of the interconverting enantiomers, the peak widths at half height wA and wB, and the relative plateau height hp), and the initial amounts A0 and B0 of the enantiomers without any iterative and time consuming computational step. Therefore, this equation is no longer limited to racemic analytes. The analytical solution presented here was validated by comparison with a dataset of 125,000 simulated elution profiles of enantiomerizations. Furthermore, it was found that the recovery rate from a defined dataset is on average 40% higher using the unified equation compared to evaluation methods based on iterative computer simulation. The new equation was applied to determine the enantiomerization rate constant of 1-n-butyl-2-tert-butyldiaziridine by enantioselective gas chromatography. The activation parameters (DeltaH(double dagger) = 112.6 +/- 2.5 kJ/mol and DeltaS(double dagger) = -27 +/- 2 J/(K mol) were obtained from temperature-dependent measurements between 100 degrees C and 140 degrees C in 10K steps.

Entities:  

Year:  2006        PMID: 16642493     DOI: 10.1002/chir.20276

Source DB:  PubMed          Journal:  Chirality        ISSN: 0899-0042            Impact factor:   2.437


  4 in total

1.  Efficient Amplification in Soai's Asymmetric Autocatalysis by a Transient Stereodynamic Catalyst.

Authors:  Oliver Trapp
Journal:  Front Chem       Date:  2020-12-09       Impact factor: 5.221

2.  Bicyclic Phenyl-Ethynyl Architectures: Synthesis of a 1,4-Bis(phenylbuta-1,3-diyn-1-yl) Benzene Banister.

Authors:  Linda Maria Bannwart; Thomas Müntener; Michel Rickhaus; Lukas Jundt; Daniel Häussinger; Marcel Mayor
Journal:  Chemistry       Date:  2021-03-03       Impact factor: 5.236

3.  Chromatographically separable rotamers of an unhindered amide.

Authors:  Mario Geffe; Lars Andernach; Oliver Trapp; Till Opatz
Journal:  Beilstein J Org Chem       Date:  2014-03-21       Impact factor: 2.883

4.  Photochemical synthesis and properties of 1,6- and 1,8-naphthalenophanes.

Authors:  Pablo Wessig; Annika Matthes
Journal:  Molecules       Date:  2013-01-21       Impact factor: 4.411

  4 in total

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