Predominance of inductive over resonance substituent effect on 33S NMR chemical shifts of 4-substituted phenyl-4′-methylphenacyl sulfones
✍ Scribed by Ryszard Gawinecki; Erkki Kolehmainen; Andrzej Zakrzewski; Katri Laihia; Borys Ośmiałowski; Reijo Kauppinen
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 56 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
33
S NMR chemical shifts have been determined for the first time for a series of 10 substituted phenacyl sulfones. Electron-withdrawing and electron-releasing substituents in 4-substituted phenyl-4 0 -methylphenacyl sulfones, p-MeC 6 H 4 COCH 2 SO 2 C 6 H 4 R-p, cause a 'reverse' substituent effect on the 33 S NMR resonance. Dual-substituent parameter (DSP) analysis of υ( 33 S) values revealed that the inductive effect of the substituent predominates over its resonance effect. This finding shows that the 33 S NMR chemical shifts are of importance in estimating the electronic properties of sulfur-containing compounds. The 13 C and 17 O NMR chemical shifts of the title compounds are also discussed.