Issue 1, 2016

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

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
09 Aug 2015
Accepted
08 Oct 2015
First published
08 Oct 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 329-332

Author version available

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

T. A. Brown, N. Hosseini-Nassab, H. Chen and R. N. Zare, Chem. Sci., 2016, 7, 329 DOI: 10.1039/C5SC02939B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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