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High-throughput and Comprehensive Drug Surveillance Using Multisegment Injection-Capillary Electrophoresis-Mass Spectrometry

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On-line linear sweep voltammetry-electrospray mass spectrometry.

W Lu¹, X Xu, R B Cole

¹Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148.

Analytical Chemistry

|June 7, 2011

Summary

This study introduces an on-line linear sweep voltammetry-electrospray mass spectrometry technique for analyzing electrochemical reactions. The method successfully identified intermediates and products from diphenyl sulfide oxidation, 9,10-diphenylanthracene pyridation, and nitrobenzene reduction.

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Area of Science:

Analytical Chemistry
Electrochemistry
Mass Spectrometry

Background:

Electrochemical reactions generate transient intermediates and products that are challenging to characterize.
On-line coupling of electrochemical techniques with mass spectrometry offers a powerful approach for real-time analysis.

Purpose of the Study:

To develop and validate a three-electrode electrochemical cell coupled to an electrospray mass spectrometer for on-line electrochemical reaction studies.
To investigate the reaction mechanisms and identify products of diphenyl sulfide oxidation, 9,10-diphenylanthracene pyridation, and nitrobenzene reduction.

Main Methods:

On-line linear sweep voltammetry coupled with electrospray mass spectrometry (LSV-ES-MS).
Utilized a three-electrode electrochemical cell integrated with an ES mass spectrometer.
Analyzed ion abundance versus potential profiles to determine molecular weight and structural information.

Main Results:

Successfully identified intermediates and products from the anodic oxidation of diphenyl sulfide, including diphenyl sulfoxide and pseudodimer sulfonium ion.
Provided evidence supporting proposed mechanisms for pseudodimer sulfonium ion generation and pyridine addition to 9,10-diphenylanthracene radical cation.
Discovered a new reaction product, [DPA(py) - H](+), from the pyridation of 9,10-diphenylanthracene.
Detected intermediates and products of nitrobenzene reduction in both positive and negative electrospray ionization modes, overcoming inherent oxidation tendencies of ES.

Conclusions:

The developed LSV-ES-MS system is effective for on-line characterization of electrochemical reaction intermediates and products.
The technique provides valuable molecular weight and structural insights, aiding in the elucidation of reaction mechanisms.
The method demonstrates versatility in analyzing both oxidation and reduction processes across various media.