Abstract
The unimolecular rearrangement chemistry of molecular ions encountered in mass spectrometers is ideally suited for stereoanalytical purposes. This follows from the spatial dependency of the bond making stage of the rearrangement. Examples are noted which demonstrate how such rearrangements may be utilized to assign configuration with and without deuterium labelling even when only one stereoisomer is available. These rearrangements may occur from molecular ions generated by electron impact or field ionization. Chemical ionization and ion cyclotron resonance mass spectrometry are known to be sensitive to stereoisomerism but have yet to be developed as stereoanalytical devices. Simple cleavage reactions of molecular ions may reveal stereoisomeric information when two diastereomers give rise to identical product ions. In the latter case appearance potential differences and product intensities differences mirror the enthalpic differences of the precursor neutral diastereomers. These thermochemical effects could be utilized to assign configuration to stereoisomers.
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