Observation of electrochemically generated nitrenium ions by desorption electrospray ionization mass spectrometry

Timothy A. Brown, Niloufar Hosseini-Nassab, Hao Chen, Richard N. Zare

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

We report the observation of the electrochemically generated nitrenium ions of 4,4′-dimethyoxydiphenylamine and di-p-tolylamine in solution by mass spectrometry. This setup takes inspiration from desorption electrospray ionization mass spectrometry to sample directly from the surface of a rotating waterwheel working electrode for mass spectrometric analysis. Detection of the 4,4′-dimethyoxydiphenylamine nitrenium ion was expected based upon para-methoxy resonance stabilization, whereas observation of the di-p-tolylamine nitrenium ion might be unexpected because resonance stabilization from the para-substituted position is unavailable. However, the short timescale analysis of the setup allows for the isolation of the di-p-tolylamine nitrenium ion, which is electrogenerated in solution and detected mass spectrometrically.

Original languageEnglish (US)
Pages (from-to)329-332
Number of pages4
JournalChemical Science
Volume7
Issue number1
DOIs
StatePublished - Jan 1 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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