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The effect of molecular geometry on the electron‐impact‐induced fragmentation of 3,4‐diethylmuconates
Author(s) -
GilAv E.,
Leftin J. H.,
Mandelbaum A.,
Weinstein S.
Publication year - 1970
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.1210040148
Subject(s) - fragmentation (computing) , methanol , chemistry , cis–trans isomerism , mass spectrum , allylic rearrangement , electron ionization , ion , hydrogen , polyatomic ion , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis , ionization , computer science , operating system
The isomeric 3,4‐diethylmuconic acid dimethyl esters behave differently under electronimpact. Methanol elimination from the molecular ion is one of the most important processes in the trans, trans diester. In the cis, cis and cis, trans isomers, however, the loss of a methoxyl radical from the molecular ion occurs to a much greater extent than elimination of methanol. This distinctive behaviour is interpreted in terms of different distances between the methoxy groups and the allylic hydrogen atoms in the geometrical isomers. Other differences in the mass spectra of the isomers are reported and discussed.