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

Published

Author(s)

Kirill V. Tretyakov, Nino G. Todua, Roman S. Borisov, Vladimir G. Zaikin, Stephen Stein, Anzor I. Mikaia

Abstract

A new kind of "para-effect" under EI conditions has been discovered for a series of bis(perfluoroacyl) derivatives of o-, m- and p- phenylendiamines, hydroxybenzeneamines and mercaptobenzeneamines of a common structure RCOX C6H4 NHCOR (X = NH, S, O; R = CF3, C2F5, C3F7). Only para-isomers showed successive loss of radical RCO and 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.
Citation
Rapid Communications in Mass Spectrometry
Volume
24
Issue
17

Keywords

bifunctional benzenes, bis(perfluoroacyl) derivatives, electron ionization mass spectra, para-effect

Citation

Tretyakov, K. , Todua, N. , Borisov, R. , Zaikin, V. , Stein, S. and Mikaia, A. (2010), Unique para-effect in electron ionization mass spectra of bis(perfluoroacyl) derivatives of bifunctional aminobenzenes, Rapid Communications in Mass Spectrometry, [online], https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=905023 (Accessed June 21, 2024)

Issues

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Created September 14, 2010, Updated October 12, 2021