The gas phase ion/molecule chemistry of four carbanions generated from vinylene carbonate and its methyl and dimethyl derivatives

Marin S Robinson, Fred W. Breitbeil

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4 Scopus citations


The gas phase ion/molecule chemistry of four carbanions generated by the reaction of vinylene carbonate, {A figure is presented} and its methyl and dimethyl derivatives with hydroxide ion has been investigated. From the parent the sole product is the ketenyl anion, HCCO-, arising from vinylic proton abstraction and loss of CO2. From the dimethyl derivative, abstraction of an allylic proton from one of the methyl groups followed by loss of CO2 leads exclusively to CH2CC(O)CH3. Both pathways are observed for the monomethyl derivative, leading to a mixture of the ions CH3CCO- and CH2CCHO. The ketenyl and methyl ketenyl ions do not exchange hydrogen for deuterium with D2O or CH3OD, but they do react with CS2 and COS to form the corresponding thioketenyl anions, HCCS- and CH3CCS-. The ions CH2CC(O)CH3 and CH2CCHO exchange one and three hydrogen atoms for deuterium atoms with D2O respectively, and react with CS2 to form thioketenyl anions by addition and loss of thioformaldehyde. Possible mechanisms for these reactions are discussed.

Original languageEnglish (US)
Pages (from-to)647-658
Number of pages12
JournalInternational Journal of Mass Spectrometry and Ion Processes
Issue numberC
StatePublished - Sep 1 1992
Externally publishedYes



  • carbanions
  • flowing afterglow
  • ion/molecule reactions
  • SIFT
  • vinylene carbonate

ASJC Scopus subject areas

  • Spectroscopy

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