Acetamide enolate: Formation, reactivity, and proton affinity

Michael C. Hare, Sudha S. Marimanikkuppam, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


Acetamide enolate (1) was selectively prepared in a Fourier transform mass spectrometer and a variable temperature flowing afterglow apparatus by the fluoride-induced desilylation of 2-(trimethylsilyl)acetamide. Its reactivity, proton affinity, and collision-induced dissociation spectra were explored and contrasted to its isomeric amidate anion (2). Since 1 and 2 are ambident nucleophiles, their reactivity with perfluoropropylene and perfluorobenzene was investigated. The unimolecular isomerization of 1 to 2 also was examined at temperatures up to 300°C. No rearrangement was observed under these conditions indicating that the activation barrier is at least 32 kcal mol-1. Structures and energies of acetamide, its conjugate bases, and the transition structure interconverting 1 and 2 were computed using a variety of ab initio and density functional theory approaches.

Original languageEnglish (US)
Pages (from-to)153-163
Number of pages11
JournalInternational Journal of Mass Spectrometry
StatePublished - Sep 14 2001

Bibliographical note

Funding Information:
Support from the National Science Foundation, the donors of the Petroleum Research Foundation, as administered by the American Chemical Society, the Minnesota Supercomputer Institute and the University of Minnesota–IBM Shared Research Project are gratefully acknowledged.


  • Ab initio calculations
  • Acetamide enolate
  • Ambident nucleophiles
  • CID
  • FTMS


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