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Observation of Electrochemically Generated Nitrenium Ions by Desorption Electrospray Ionization Mass Spectrometry

Observation of Electrochemically Generated Nitrenium Ions by Desorption Electrospray Ionization Mass Spectrometry

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

Chem Sci. 2016 Jan 1;7(1):329-332.

PMID: 28791096

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP620939	Di-p-tolylamine		620-93-9	Price

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