A Fundamental Tandem Mass Spectrometry Study of the Collision-Activated Dissociation of Small Deprotonated Molecules Related to Lignin

Christopher L. Marcum, Tiffany M. Jarrell, Hanyu Zhu, Benjamin C. Owen, Laura J. Haupert, Mckay Easton, Omid Hosseinaei, Joseph Bozell, John J. Nash, Hilkka I. Kenttämaa*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

The collision-activated fragmentation pathways and reaction mechanisms of 34 deprotonated model compounds representative of lignin degradation products were explored experimentally and computationally. The compounds were evaporated and ionized by using negative-ion mode electrospray ionization doped with NaOH to produce abundant deprotonated molecules. The ions were isolated and subjected to collision-activated dissociation (CAD). Their fragment ions were then isolated and also subjected to CAD. This was repeated until no further fragmentation was observed (up to MS6). This approach enabled the identification of characteristic reaction pathways and delineation of reasonable fragmentation mechanisms for deprotonated molecules containing various functional groups. The varying fragmentation patterns observed for different types of compounds allow for the identification of the functionalities in these compounds. This information was utilized to identify the presence of specific functionalities and their combinations in molecules in an organosolv lignin sample.

Original languageEnglish (US)
Pages (from-to)3513-3526
Number of pages14
JournalChemSusChem
Volume9
Issue number24
DOIs
StatePublished - Dec 20 2016

Keywords

  • collision-activated dissociation
  • lignin
  • liquid chromatography
  • mass spectrometry
  • reaction mechanisms

ASJC Scopus subject areas

  • Environmental Chemistry
  • Chemical Engineering(all)
  • Materials Science(all)
  • Energy(all)

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