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On the mechanism for loss of CO from aromatic oximes. Evidence for a nucleophilic attack from fluorine labelling
Author(s) -
Vijfhuizen Peter C.,
Van Der Schee Henk,
Terlouw Johan K.
Publication year - 1976
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.1210111111
Subject(s) - chemistry , labelling , nucleophile , lone pair , oxime , metastability , ion , deuterium , fluorine , acetophenone , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , atomic physics , physics , biochemistry , molecule , catalysis
The mehanisms for loss of CO from benzaldoxime and acetophenone oxime have been investigated with the aid of both fluorine and deuterium labelling as well as field free region metastable peak shapes. Kinetic evergy release data and the metastable ion abundance raion test were used to obtain information about the product ions. It is proposed that loss of CO from both are generated via the nucleophilic attack of the oxygen lone pair eletrons at the ortho position of the phenyl ring as the first step in the reaction sequence.