Structural Study of Phenolic Acids by Triple Quadrupole Mass Spectrometry with Electrospray Ionization in Negative Mode and H/D Isotopic Exchange

This work reports the theoretical and experimental study of fragmentation reactions in the gas phase of five phenolic acids using triple quadrupole mass spectrometry by electrospray ionization in negative ionic mode, as well as the isotope exchange experiments. MS/MS spectra were analyzed to suggest...

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Published inJournal of the Brazilian Chemical Society Vol. 31; no. 2; pp. 402 - 408
Main Authors Sinosaki, Nayane, Tonin, Angélica, Ribeiro, Marcos, Poliseli, Camila, Roberto, Sharise, da Silveira, Roberta, Visentainer, Jesuí, Santos, Oscar, Meurer, Eduardo
Format Journal Article
LanguageEnglish
Portuguese
Published Sociedade Brasileira de Química 01.02.2020
Subjects
CHEMISTRY, MULTIDISCIPLINARY
mass spectrometry
structural study
fragmentation
phenolic
CID
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Summary:This work reports the theoretical and experimental study of fragmentation reactions in the gas phase of five phenolic acids using triple quadrupole mass spectrometry by electrospray ionization in negative ionic mode, as well as the isotope exchange experiments. MS/MS spectra were analyzed to suggest the fragmentation mechanisms, while theoretical calculations at the theory level B3LYP/6-311+G** were performed to expose the proposed mechanisms viability for this class of compounds. As expected, compounds with aromatic methoxy substitution presented •CH3 radical elimination as the principal fragmentation pathway, forming dystonic ions. Compounds without methoxy substituents dissociate with higher energies losing the CO2, CO and H2O. The isotopic marking experiments indicated the exchange of hydrogens by deuterases in the hydroxyl protons, which corroborates with the proposed mechanisms.
ISSN:0103-5053
1678-4790
DOI:10.21577/0103-5053.20190197