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Fragmentation of some even‐electron nitroaromatic ions: The question of the nitrotropylium ion
Author(s) -
Shapiro Robert H.,
Serum James W.
Publication year - 1969
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.1210020507
Subject(s) - fragmentation (computing) , ion , chemistry , nitro , yield (engineering) , electron ionization , mass spectrum , electron , cleavage (geology) , mass spectrometry , medicinal chemistry , analytical chemistry (journal) , organic chemistry , materials science , physics , chromatography , ionization , quantum mechanics , fracture (geology) , computer science , metallurgy , composite material , operating system , alkyl
The behavior of the even‐electron mass 150 ions, (presumably nitrobenzoyl cations) generated by simple α‐cleavage of m ‐ and p ‐nitrobenzoic acid derivatives, undergo two competing secondary fragmentations to yield odd‐electron ions by the expulsion of NO and NO 2 . Expulsion of NO from the mass 150 ions from p ‐nitro compounds is far greater than expulsion of NO from those generated from m ‐nitro compounds. In addition, the behavior of the even‐electron mass 136 ions, generated from m ‐ and p ‐nitrobenzyl compounds, was compared to that of the mass 150 ions and they were found to decompose in a similar fashion. From our results we conclude that the decomposing mass 136 ions produced from either the m ‐ or p ‐nitrobenzyl compounds, or both, do not have the nitropylium structure; our data are more consistent with the decomposing ions having nitrobenzyl structures.