ArticleJournal of the American Society for Mass Spectrometry2013
Mass spectrometric study of the gas-phase difluorocarbene expulsion of polyfluorophenyl cations via F-atom migration.
Article in Journal of the American Society for Mass Spectrometry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
5 citing papers in PubMed.
- Interactive Software for Interpreting and Curating High-Resolution Electron Ionization Mass Spectra.Journal of mass spectrometry : JMS · 2026Article
- New Perspectives in the Noble Gas Chemistry Opened by Electrophilic Anions.Frontiers in chemistry · 2020Article
- Sulfur Transfer Versus Phenyl Ring Transfer in the Gas Phase: Sequential Loss of CHJournal of the American Society for Mass Spectrometry · 2019Article
- Intramolecular Halogen Atom Coordinated H Transfer via Ion-Neutral Complex in the Gas Phase Dissociation of Protonated Dichlorvos Derivatives.Journal of the American Society for Mass Spectrometry · 2017Article
- Intramolecular Halogen Transfer via Halonium Ion Intermediates in the Gas Phase.Journal of the American Society for Mass Spectrometry · 2016Article
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
An increasing number of fluorinated drugs, pesticides, and fine chemicals are now produced and applied, especially those containing polyfluorinated aromatic moieties. However, at present, the extent of literature covering the special mass spectrometric behaviors of these compounds remains limited. Herein, we report an unexpected but also general gas-phase dissociation mode of polyfluorinated aromatics in mass spectrometry: expulsion of difluorocarbene (50-Da neutral loss). Results from accurate mass measurements, tandem mass spectrometric experiments, and density functional theory (DFT) calculations support an intramolecular F-atom “ring-walk” migration mechanism for gas-phase CF2 loss. Based on an assessment of the electron ionization-mass spectrometry (EI-MS) data of more than 40 polyfluorinated aromatic compounds from the National Institute of Standards and Technology data bank, we generalized on the substitution group effects on the difluorocarbene dissociation process of polyfluorinated aromatic compounds in EI-MS. These studies have enriched our knowledge of the special gas-phase reactivity of polyfluorinated aromatics and will provide valuable information in further analytical research of these compounds by mass spectrometry.
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