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Electron Capture Mass Spectrometry of Phenylsulfonyl‐1,4‐benzoquinones and 2‐Phenylsulfonyl‐1,4‐naphthoquinone
Author(s) -
Boote V.A.,
Bruce J.M.,
Clarke S.A.,
Speak R.J.
Publication year - 1997
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/(sici)1097-0231(19970422)11:7<753::aid-rcm800>3.0.co;2-8
Subject(s) - chemistry , quinone , fragmentation (computing) , semiquinone , naphthoquinone , hydroquinone , vicinal , benzoquinone , mass spectrometry , aryne , medicinal chemistry , photochemistry , stereochemistry , organic chemistry , chromatography , computer science , operating system
Electron capture mass spectrometry of phenylsulfonyl‐1,4‐benzoquinone and some of its di‐ and trimethyl homologues and of 2‐phenylsulfonyl‐1,4‐naphthoquinone, using CO 2 ‐buffered thermal electrons demonstrates the existence in the plasma of two competing processes: loss of C 6 H 4 , suggested to be benzyne, from the semiquinone anion radical, and loss of C 6 H 5 , as a phenyl radical, from the corresponding hydroquinone formed by concomitant reduction of the quinone in the source. Fragmentation to C 6 H 4 predominates when the 3‐position ( vicinal to phenylsulfonyl) of the quinone is unsubstituted. Similar fragmentations are observed for the corresponding phenylsulfonylhydroquinones, which are oxidized in situ to the quinones. Fragmentation mechanisms are suggested. © 1997 John Wiley & Sons, Ltd.