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Ortho , Effects in organic molecules on electron impact: X—unusual ortho effects of the methyl group in o ‐picolinotoluidide
Author(s) -
Ramana D. V.,
Sundaram N.
Publication year - 1982
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.1210171003
Subject(s) - chemistry , ion , mass spectrum , pyridine , methyl group , molecule , polyatomic ion , mass spectrometry , radical , electron ionization , nitrogen , kinetic energy , ring (chemistry) , analytical chemistry (journal) , stereochemistry , crystallography , medicinal chemistry , group (periodic table) , organic chemistry , physics , chromatography , quantum mechanics , ionization
The mass spectrum of o ‐picolinotoluidide gives rise to three major fragments at m/z 184, m/z 169 and m/z 168, corresponding to the loss of CO from the molecular ion followed by the loss of ṄH 2 and ĊH 3 by independent pathways. It has been shown that the ortho methyl group and the nitrogen of the pyridine ring in the 2‐position are involved in the formation of these three major fragments observed in the mass spectrum of o ‐picolinotoluidide. The mass spectrum of 2‐( o ‐toluidino) pyridine, the molecular ion of which can resemble the [MCO] + ion in o‐picolinotoluidide, also shows loss of CH 3 and NH 2 radicals from the molecular ions. Based on these observations coupled with the high resolution data, the mass analysed ion kinetic energy spectrometry and high voltage scans of these fragments in both the compounds, two mechanistic pathways have been proposed for the formation of these ions in o ‐picolinotoluidide.