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Some PhCNO‐containing molecules; mass spectral similarity and molecular diversity
Author(s) -
Deem M. L.
Publication year - 1980
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.1210151106
Subject(s) - moiety , chemistry , molecule , benzonitrile , ion , polyatomic ion , cleave , metastability , stereochemistry , electron ionization , crystallography , photochemistry , medicinal chemistry , organic chemistry , enzyme , ionization
Abstract Some diverse compounds possessing a PhCNO unit cleave the NO link upon electron impact to give [PhCN] + ˙. Different and especially significant modes of NO scission occur in metastable processes when the oxygen atom of the PhCNO group is exocyclic to a heterocyclic nitrogen atom. Upon electron impact, rupture of the NO bond in PhCNO‐containing molecules generally dominates over 1,3‐dipolar cycloreversion, which generates the radical cation of benzonitrile oxide. Stable PhCNO‐containing molecules survive competing fragmentations in the ion source to produce [M+H] + ions of moderate relative intensity. Other ions, which are larger than [M] + are implicated where M is PhCHNOR. Several values of m / z for metastable ions are common to compounds which have a PhCNO moiety. These m / z values generally derive both from a parent ion with m / z ⩽105 and from a PhCNO moiety.