1H and 13C NMR spectroscopic study of oxidation of D,L-cystine and 3,3′-dithiobis(propionic acid) with hydrogen peroxide in aqueous solution

✍ Scribed by Alan R. Katritzky; Novruz G. Akhmedov; Olga V. Denisko

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 129 KB
• Volume: 41
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1110

✦ Synopsis

Abstract

The oxidation of symmetrical disulfides [D,L‐cystine (1) and 3,3′‐dithiobis(propionic acid) (2)] with hydrogen peroxide in D~2~O–NaOH solution (pH 10–11) was studied by NMR spectroscopy. Assignments of the proton and carbon NMR signals of starting materials (1 and 2) and products of oxidation are based on conventional 1D NMR methods (DEPT, selective spin decoupling). Formation of C—S bond cleavage products or, in case of 2, partially oxidized intermediates was not detected. The accelerating effect of Cu^2+^ cations, but not Fe^3+^ cations, on the oxidation rate of 1 in basic medium was demonstrated. Copyright © 2002 John Wiley & Sons, Ltd.