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Observed and calculated 1H and 13C chemical shifts induced by the in situ oxidation of model sulfides to sulfoxides and sulfones

✍ Scribed by Martin Dračínský; Radek Pohl; Lenka Slavětínská; Miloš Buděšínský

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
322 KB
Volume
48
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

A series of model sulfides was oxidized in the NMR sample tube to sulfoxides and sulfones by the stepwise addition of meta‐chloroperbenzoic acid in deuterochloroform. Various methods of quantum chemical calculations have been tested to reproduce the observed ^1^H and ^13^C chemical shifts of the starting sulfides and their oxidation products. It has been shown that the determination of the energy‐minimized conformation is a very important condition for obtaining realistic data in the subsequent calculation of the NMR chemical shifts. The correlation between calculated and observed chemical shifts is very good for carbon atoms (even for the ‘cheap’ DFT B3LYP/6‐31G* method) and somewhat less satisfactory for hydrogen atoms. The calculated chemical shifts induced by oxidation (the Δδ values) agree even better with the experimental values and can also be used to determine the oxidation state of the sulfur atom (S, SO, SO~2~). Copyright © 2010 John Wiley & Sons, Ltd.

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