6533b7dbfe1ef96bd127140a
RESEARCH PRODUCT
Predominance of inductive over resonance substituent effect on33S NMR chemical shifts of 4-substituted phenyl-4′-methylphenacyl sulfones
Erkki KolehmainenReijo KauppinenKatri LaihiaRyszard GawineckiBorys OśmiałowskiAndrzej Zakrzewskisubject
ChemistryStereochemistryCarbon-13 NMR satelliteChemical shiftSubstituentGeneral ChemistryCarbon-13 NMRResonance (chemistry)PhenacylMedicinal chemistrychemistry.chemical_compoundGeneral Materials ScienceInductive effectResonance effectdescription
33S 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′-methylphenacyl sulfones, p-MeC6H4COCH2SO2C6H4R-p, cause a ‘reverse’ substituent effect on the 33S NMR resonance. Dual-substituent parameter (DSP) analysis of δ(33S) values revealed that the inductive effect of the substituent predominates over its resonance effect. This finding shows that the 33S NMR chemical shifts are of importance in estimating the electronic properties of sulfur-containing compounds. The 13C and 17O NMR chemical shifts of the title compounds are also discussed. Copyright © 1999 John Wiley & Sons, Ltd.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1999-06-01 | Magnetic Resonance in Chemistry |