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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Studies in Mass Spectrometry. II. Random Hydrogen Rearrangement in Aromatic Molecular Ions

CG Macdonald and JS Shannon

Australian Journal of Chemistry 15(4) 771 - 785
Published: 1962

Abstract

To provide data for investigations by, inter alia, mass-spectrometric methods into the deuterium exchange of the aromatic hydrogen of some coal fractions, a study was made which confirmed the occurrence of completely random hydrogen rearrangement prior to or during the elimination of C2H2 in the molecular ions of benzene-1,2,3-d3, benzene-l,3,5-d3, naphthalene-1,2,3,4-d4, naphthalene-1,4,5,8-d4, and phenanthrene-9,10-d2, and in the phenyl ions derived from o-bromobenzene-d, m-bromobenzene-d, and p-chlorobenzene-d, Similar but incomplete hydrogen rearrangement was found to occur in the molecular ion of carbazole-N-d prior to or during elimination of HCN. Such rearrangements, for which mechanistic considerations are presented, must be taken into account when the mass spectra of deuterium-substituted aromatic compounds are being interpreted.

https://doi.org/10.1071/CH9620771

© CSIRO 1962

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