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Chiral Derivatization of Hydroxycarboxylic Acids Using 2,4,6-Trichlorobenzoyl Chloride as a Highly Efficient Regioselective Esterification Reagent for Gas Chromatography-Mass Spectrometry
Mass Spectrometry Letters / Mass Spectrometry Letters, (P)2233-4203; (E)2093-8950
2020, v.11 no.4, pp.103-107
https://doi.org/10.5478/MSL.2020.11.4.103
(Department of Chemistry, Gachon University)
(Department of Chemistry, Gachon University)
(Department of Chemistry, Gachon University)
Park,
J. H., &
Han,
S.
Y.
(2020). Chiral Derivatization of Hydroxycarboxylic Acids Using 2,4,6-Trichlorobenzoyl Chloride as a Highly Efficient Regioselective Esterification Reagent for Gas Chromatography-Mass Spectrometry. Mass Spectrometry Letters, 11(4), 103-107, https://doi.org/10.5478/MSL.2020.11.4.103
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Abstract
We report the application of 2,4,6-trichlorobenzoyl chloride (often referred to as Yamaguchi esterification reagent) for the selective derivatization of the carboxylic group for GC-MS with the sample preparation method optimized for GC-MS analysis. The reagent was shown to be capable of selectively turning the carboxylic group into a reaction center, i.e., anhydride, of which the further reaction was directed to a near complete formation of required esters by unique steric and electronic effects of the reagent. Using the developed method, the chiral separation of hydroxycarboxylic acids by GC-MS using non-chiral col-umns was successfully demonstrated.
- keywords
- 2, 4, 6-trichlorobenzoyl chloride, chiral separation, GC-MS, hydroxycarboxylic acids, O-acetylated L-menthyl esters
- Submission Date
- 2020-12-14
- Revised Date
- 2020-12-23
- Accepted Date
- 2020-12-23
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