Generation of gas-phase sodiated arenes such as [Na3(C 6H4)+] from benzene dicarboxylate salts

Athula B. Attygalle, Chang Ching Chan, Frank U. Axe, Mark Bolgar

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Upon collision-induced activation, gaseous sodium adducts generated by electrospray ionization of disodium salts of 1,2- 1,3-, and 1,4-benzene dicarboxylic acids (m/z 233) undergo an unprecedented expulsion of CO 2 by a rearrangement process to produce an ion of m/z 189 in which all three sodium atoms are retained. When isolated in a collision cell of a tandem-in-space mass spectrometer, and subjected to collision-induced dissociation (CID), only the m/z 189 ions derived from the meta and para isomers underwent a further CO2 loss to produce a peak at m/z 145 for a sodiated arene of formula (Na3C6H4) +. This previously unreported m/z 145 ion, which is useful to differentiate meta and para benzene dicarboxylates from their ortho isomer, is in fact the sodium adduct of phenelenedisodium. Moreover, the m/z 189 ion from all three isomers readily expelled a sodium radical to produce a peak atm/z 166 for a radical cation [(C6H4CO 2Na2)+], which then eliminated CO2 to produce a peak atm/z 122 for the distonic cation (C 6H4Na2)+.

Original languageEnglish
Pages (from-to)72-81
Number of pages10
JournalJournal of Mass Spectrometry
Volume45
Issue number1
DOIs
StatePublished - Jan 2010

Keywords

  • Benzene dicarboxylic acids
  • Collision-induced dissociation
  • Positive ions
  • Sodiated arenes
  • Sodium adducts

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