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Electron impact fragmentation of 2‐arylhydrazonopropandioic acid derivatives
Author(s) -
Kallury R. Krishna Mohan Rao,
Loudon Alexander G.
Publication year - 1979
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.1210140503
Subject(s) - chemistry , fragmentation (computing) , moiety , amine gas treating , diazirine , ion , mass spectrum , deuterium , metastability , polyatomic ion , electron ionization , photochemistry , medicinal chemistry , phenol , computational chemistry , stereochemistry , organic chemistry , ionization , physics , quantum mechanics , computer science , operating system
Abstract Examination of the mass spectra of eleven 2‐arylhydrazonopropandioic acid derivatives reveals that a radical ion which is tentatively formulated as a 1 H ‐diazirine species is produced in each case (except for the diphenyl este) by more than one process. Formation of what is formally the aryl amine radical ion occurs by a novel hydrogen rearrangement. Simple cleavage of the bonds β to either the aromatic ring or the CN moiety also produces abundant ions. The diphenyl ester behaves anomalously yielding the phenol ion instead of the amine. The proposed mechanisms were confirmed by metastable studies, deuterium labelling and exact mass measurements.