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Elimination of difluorocarbene from the molecular ions of α,α,α‐Trifluorocresols with a fluorine atom migration in an ion trap mass spectrometer
Author(s) -
Tajima Susumu,
Takahashi Shinya,
Sekiguchi Osamu
Publication year - 1999
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(19990730)13:14<1458::aid-rcm667>3.0.co;2-l
Subject(s) - difluorocarbene , chemistry , ion , mass spectrum , ring (chemistry) , ion trap , mass spectrometry , quadrupole ion trap , fluorine , trifluoromethyl , benzene , dissociation (chemistry) , atom (system on chip) , medicinal chemistry , organic chemistry , alkyl , chromatography , computer science , embedded system
The elimination of difluorocarbene (CF 2 ) from the molecular ions of m ‐α,α,α‐trifluorocresol (MW 162, 1) and p ‐α, α, α‐trifluorocresol (MW 162, 2) upon electron impact have been investigated using a quadrupole ion trap mass spectrometer. This reaction involves a fluorine (F) atom migration from the trifluoromethyl group to the benzene ring. In the case of 1, an F atom migrates via a four‐membered ring transition state to give rise to the molecular ion of p ‐fluorophenol (MW 112, 5) and a small amount of o ‐fluorophenol (MW 112, 3). On the other hand, in the case of 2, an F atom migrates to the ipso position of the benzene ring via a three‐membered ring transition state to give rise to 5 + . These conclusions were confirmed by the comparison of the energy‐resolved mass spectra (collision‐induced dissociation (CID) spectra versus collision energy) of the m/z 112 ions from 1 + and 2 + with those of reference compounds, o ‐, m ‐ and p ‐fluorophenol (3–5). Copyright © 1999 John Wiley & Sons, Ltd.