On reduction of the drug diflunisal in non-aqueous media

The electrochemical reduction of diflunisal was studied in dimethyl sulfoxide on static mercury drop electrode. Diflunisal yields one irreversible wave at −1.2 V (vs. Ag | AgCl | 1 M LiCl electrode) due to the reduction of the carboxylic functional group in the molecule. The electrochemical properti...

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Bibliographic Details
Published in:Monatshefte für Chemie 2015-05, Vol.146 (5), p.807-812
Main Authors: Tiribilli, Chiara, Sokolová, Romana, Giannarelli, Stefania, Valášek, Michal
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
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Summary:The electrochemical reduction of diflunisal was studied in dimethyl sulfoxide on static mercury drop electrode. Diflunisal yields one irreversible wave at −1.2 V (vs. Ag | AgCl | 1 M LiCl electrode) due to the reduction of the carboxylic functional group in the molecule. The electrochemical properties of the drug were compared with the ones of the chlorinated analogue. The study is based on cyclic voltammetry, tast polarography, and constant potential electrolysis. The experimental findings are supported by molecular orbital calculations. The mechanism of reduction of the carboxylic moiety was found to involve two electrons and two protons. The reduction pathway leads to formation of an aldehyde derivative. Graphical Abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-014-1390-7