Unique para-effect in electron ionization mass spectra of bis(perfluoroacyl) derivatives of bifunctional aminobenzenes

A new kind of ‘para‐effect’ under electron ionization (EI) conditions has been discovered for a series of bis(perfluoroacyl) derivatives of o‐, m‐ and p‐phenylenediamines, ‐hydroxybenzeneamines and ‐mercaptobenzeneamines of a common structure RCOX–C6H4–NHCOR (X = NH, S, O; R = CF3, C2F5, C3F7). Only...

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Published in:Rapid communications in mass spectrometry 2010-09, Vol.24 (17), p.2529-2532
Main Authors: Tretyakov, Kirill V., Todua, Nino G., Borisov, Roman S., Zaikin, Vladimir G., Stein, Stephen E., Mikaia, Anzor I.
Format: Article
Language:English
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Ions
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Summary:A new kind of ‘para‐effect’ under electron ionization (EI) conditions has been discovered for a series of bis(perfluoroacyl) derivatives of o‐, m‐ and p‐phenylenediamines, ‐hydroxybenzeneamines and ‐mercaptobenzeneamines of a common structure RCOX–C6H4–NHCOR (X = NH, S, O; R = CF3, C2F5, C3F7). Only the para‐isomers showed successive loss of a radical RCO• and a molecule RCN, leading to very intense peaks in the EI spectra. The composition and the origin of the [M–COR–NCR]+ ions were confirmed by exact mass measurements and linked scan experiments. The proposed mechanism of their formation takes into account likely para‐quinoid structures of the precursor ions. A similar rearrangement has not been observed for para‐isomers in the series of bis(perfluoroacyl) derivatives of benzenediols, mercaptophenols and dimercaptobenzenes. Published in 2010 by John Wiley & Sons, Ltd.
ISSN:0951-4198
1097-0231
1097-0231
DOI:10.1002/rcm.4661