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Atmospheric pressure chemical ionization of fluorinated phenols in atmospheric pressure chemical ionization mass spectrometry, tandem mass spectrometry, and ion mobility spectrometryAtmospheric pressure chemical ionization (APCI)-mass spectrometry (MS) for fluorinated phenols (C6H5-xFxOH Where x = 0-5) in nitrogen with Cl- as the reagent ion yielded product ions of M Cl- through ion associations or (M-H)- through proton abstractions. Proton abstraction was controllable by potentials on the orifice and first lens, suggesting that some proton abstraction occurs through collision induced dissociation (CID) in the interface region. This was proven using CID of adduct ions (M Cl-) with Q2 studies where adduct ions were dissociated to Cl- or proton abstracted to (M-H)-. The extent of proton abstraction depended upon ion energy and structure in order of calculated acidities: pentafluorophenol > tetrafluorophenol > trifluorophenol > difluorophenol. Little or no proton abstraction occurred for fluorophenol, phenol, or benzyl alcohol analogs. Ion mobility spectrometry was used to determine if proton abstraction reactions passed through an adduct intermediate with thermalized ions and mobility spectra for all chemicals were obtained from 25 to 200 degrees C. Proton abstraction from M Cl- was not observed at any temperature for phenol, monofluorophenol, or difluorophenol. Mobility spectra for trifluorophenol revealed the kinetic transformations to (M-H)- either from M Cl- or from M2 Cl- directly. Proton abstraction was the predominant reaction for tetra- and penta-fluorophenols. Consequently, the evidence suggests that proton abstraction occurs from an adduct ion where the reaction barrier is reduced with increasing acidity of the O-H bond in C6H5-xFxOH.
Document ID
20040112173
Acquisition Source
Legacy CDMS
Document Type
Reprint (Version printed in journal)
Authors
Eiceman, G. A.
(New Mexico State University Las Cruces, United States)
Bergloff, J. F.
Rodriguez, J. E.
Munro, W.
Karpas, Z.
Date Acquired
August 21, 2013
Publication Date
November 1, 1999
Publication Information
Publication: Journal of the American Society for Mass Spectrometry
Volume: 10
Issue: 11
ISSN: 1044-0305
Subject Category
Life Sciences (General)
Funding Number(s)
CONTRACT_GRANT: DAAH04-95-1-0541
CONTRACT_GRANT: NAGY4-558
Distribution Limits
Public
Copyright
Other
Keywords
NASA Discipline Environmental Health
Non-NASA Center

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