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Benzyl vs. tropylium ions in the decomposition of some alkylnitrobenzenes
Author(s) -
Westwood R.,
Williams Dudley H.,
Yeo Adrian N. H.
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.1210031204
Subject(s) - cycloheptatriene , ion , ring (chemistry) , decomposition , chemistry , alkyl , hydrogen , internal energy , medicinal chemistry , photochemistry , physics , organic chemistry , quantum mechanics
The [NO 2 C 7 H 6 ] + ions generated from m ‐alkylnitrobenzenes have been shown to be different in their decomposition from those generated from p ‐alkylnitrobenzenes, even when the alkyl group is methyl and the departing fragment a hydrogen radical. Thus, in these cases even molecular ions of relatively high internal energy do not reversibly ring‐expand to cycloheptatriene structures. In addition, the [NO 2 C 7 H 6 ] + ions, assumed to be benzylic, do not ring‐expand to nitrotropylium ions at internal energies sufficient to cause subsequent loss of NO or NO 2 from the p ‐ and m ‐isomers, respectively.