Fast and precise access to enantiomerization rate constants in dynamic chromatography

Chirality
Oliver Trapp

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 mea...Continue Reading

References

Jul 10, 2003·Chemical Reviews·Christophe Dugave, Luc Demange
Feb 24, 2004·Chemistry : a European Journal·O TrappR G Kostyanovsky
Dec 8, 2004·Archives of Biochemistry and Biophysics·Laura S Busenlehner, Richard N Armstrong

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Citations

Aug 8, 2014·Chemical Communications : Chem Comm·Skrollan StockingerOliver Trapp
Nov 26, 2010·Journal of Chromatography. a·Marina M CarrozzoCarlo Parenti
Nov 10, 2009·Journal of Chromatography. a·Luisa PastiFrancesco Dondi
Sep 9, 2009·Journal of Pharmaceutical and Biomedical Analysis·Enqi WuJong Seong Kang
Jan 31, 2013·Chemistry : a European Journal·Anoklase J-L AyitouJ Sivaguru
Jan 3, 2013·Chirality·Frank Maier, Oliver Trapp
Feb 13, 2013·Chirality·Matthias Kamuf, Oliver Trapp
Sep 21, 2011·Chirality·Giuseppe CannazzaCarlo Parenti
Sep 17, 2010·Chirality·Matthias Kamuf, Oliver Trapp
Jun 6, 2009·Chirality·Oliver TrappWerner Könen
Apr 12, 2016·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Bernard TestaAlessandro Pedretti
Jul 5, 2011·Journal of Pharmaceutical and Biomedical Analysis·Chu Van MenSang-Hun Jung
Feb 26, 2015·Physical Chemistry Chemical Physics : PCCP·Angela BihlmeierWim Klopper
Apr 25, 2013·Organic Letters·Jie ZongRobert A Pascal
Apr 30, 2014·Beilstein Journal of Organic Chemistry·Mario GeffeTill Opatz
Jan 28, 2021·Chemistry : a European Journal·Linda Maria BannwartMarcel Mayor
Jul 12, 2019·Chemical Reviews·Kais DhbaibiJeanne Crassous
Feb 9, 2007·The Journal of Physical Chemistry. a·Ibon AlkortaKrzysztof Zborowski

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