"Meta elimination," a diagnostic fragmentation in mass spectrometry

Athula B. Attygalle, Upul Nishshanka, Carl S. Weisbecker

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

The diagnostic value of the "ortho effect" for unknown identification by mass spectrometry is well known. Here, we report the existence of a novel "meta effect," which adds to the repertoire of useful mass spectrometric fragmentation mechanisms. For example, the meta-specific elimination pathway described in this report enables unequivocal identification of meta isomers from ortho and para isomers of carboxyanilides. The reaction follows a specific path to eliminate a molecule of meta-benzyne, from the anion produced after the initial decarboxylation of the precursor. Consequently, in the CID spectra of carboxyanilides, a peak for the (R-CO-NH) - anion is observed only for the meta isomers. For example, the peaks observed at m/z 58, 86, 120, 128, and 170 from acetamido-, butamido-, benzamido, heptamido-, and decanamido-benzoates, respectively, were specific only to the spectra of meta isomers.

Original languageEnglish
Pages (from-to)1515-1525
Number of pages11
JournalJournal of the American Society for Mass Spectrometry
Volume22
Issue number9
DOIs
StatePublished - Sep 2011

Keywords

  • Anilides
  • Anthranilic acid
  • Collision-induced dissociation
  • Meta effect
  • Meta elimination
  • Ortho effect

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