The ortho-dehydrophenoxy anion: an unusual ion formed from a surprising reaction

Gregg D. Dahlke, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


The conjugate bases of fluorobenzene and methoxybenzene react with nitrous oxide to afford the dehydrophenoxy anion (C6H3O-). The mechanism for the formation of this novel ion has been explored as has some if its reactivity. In general, the reactions of C6H3O- proceed via proton transfer, addition of the newly formed anion to the benzyne triple bond, and subsequent fragmentation. Acidities of the different ring positions in methoxybenzene are also reported.

Original languageEnglish (US)
Pages (from-to)633-645
Number of pages13
JournalInternational Journal of Mass Spectrometry and Ion Processes
Issue numberC
StatePublished - Sep 1 1992

Bibliographical note

Funding Information:
The kindnessa nd generosityo f ProfessorC .H. DePuy, in whosel aboratory the first observationsre portedi n this studyw erem ade,i s gratefullya cknow-ledged. Generous allocations of computer resourcesf rom the Minnesota SupercomputerIn stitute and financial support from the National Science Foundation (CHE-8907198)a nd the donors of the Petroleum Research Foundation, as administeredb y the American Chemical Society, are also appreciated.


  • Gas phase
  • flowing afterglow
  • fluorobenzene
  • methoxybenzene
  • ortho-dehydrophenoxy anion


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