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Evidence for aryl participation in mass spectrometric fragmentation processes
Author(s) -
Richter W. J.,
Vetter W.
Publication year - 1969
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.1210020803
Subject(s) - heterolysis , oxonium ion , chemistry , fragmentation (computing) , ion , aryl , dissociation (chemistry) , mass spectrometry , electron ionization , photochemistry , medicinal chemistry , alkyl , organic chemistry , ionization , chromatography , computer science , catalysis , operating system
While heterolysis of oxonium ions generated upon electron‐impact in the mass spectrometer is a well documented phenomenon in the fragmentation of aliphatic ethers, little analogy exists for structurally comparable immonium ions. Exceptions are ions of the latter class in which dissociation is facilitated by the presence of proper substituents in position allowing satabilization of daughter ions. Two main types of subtitution were explored providing(1) resonance stabilization of the product ions by aryl substituents in benzylic ,heterolysis,and (2) aryl neighboring group participation in homobenzylic heterolysis, possibly yielding phenonium ions (or isometric ions via further rearrangement) as stable products in the gas phase. In the discussion emphasis will be placed on Case 2.