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Ion/molecule reactions in the gas phase: Comparison of the enantioselectivity of two chiral gases
Author(s) -
Sellier Nicole M.,
Bouillet Christine T.,
Douay David L.,
Tabet JeanClaude E.
Publication year - 1994
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290081107
Subject(s) - chemistry , ion , mass spectrometry , molecule , tandem mass spectrometry , gas phase , chirality (physics) , chemical ionization , analytical chemistry (journal) , tandem , ionization , chromatography , organic chemistry , chiral symmetry breaking , physics , materials science , quantum mechanics , nambu–jona lasinio model , composite material , quark
Stereochemistry study has always been a very important subject, but the determination of chirality has become potentially possible with the emergence of chemical ionization. In this study, mass spectrometry and tandem mass spectrometry (MS/MS) were used as a tool for distinguishing the isomers of (+) and (−) isopinocampheols and (+) and (−) menthols by ion/molecule reaction in the gas phase using two different chiral gases, G. The reactive plasma is made up of the ion GH + . Interactions between the plasma and the isomer M of (+) and (−) isopinocampheols and (+) and (−) menthols lead to the formation of the ions [M‐M 2 O+H] + , [M‐H 2 O+GH] + , [M+GH] + and [2M+H] + . In mass spectrometric analysis, their relative intensities differ because of the absolute configuration of M. In MS/MS the relative intensities of the daughter ions of [M‐H 2 O+GH] + ions enable a positive determination of (+) and (−) isomers. The susbtitution ion [M‐H 2 O+GH] + arises via an SN 2 pathway that is regioselective and sterospecific.