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Stereochemical effects in mass spectrometry. 7. Determination of absolute configuration of some organic molecules by reaction mass spectrometry
Author(s) -
Chen YaoZu,
Li Hung,
Yang HouJun,
Hua SuMing,
Li HaiQuan,
Zhao FanZhi,
Chen NenYu
Publication year - 1988
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210231205
Subject(s) - chemistry , reagent , mass spectrometry , mass spectrum , absolute configuration , molecule , analytical chemistry (journal) , ion , enantiomer , isobutane , organic chemistry , chromatography , catalysis
It was found that in the chemical ionization (isobutane) mass spectra of some asymmetric secondary alcohols and α‐amino acids, when a pair of enantiomers (such as R ‐ and S ‐2‐phenyIbutyric anhydride, R ‐ and S ‐mandelic acid, R ‐ and S ‐2‐methylbutanoic acid or R ‐ and S ‐α‐phenyl ethyl amine) were used as reaction reagents, the relative abundances of characteristic ions formed by the stereoselective reaction between sample and reagent of the same configuration were much higher than those ions formed by the sample and a reagent of a different configuration. The absolute configuration of the sample molecule may be predicted by examination of mass spectra of the sample measured with R ‐ and S ‐reagent respectively. This approach proved to be a convenient way for determination of the absolute configurations of organic molecules on a micromole level by mass Spectrometry.