Predominance of inductive over resonance substituent effect on S-33 NMR chemical shifts of 4-substituted phenyl-4 '-methylphenacyl sulfones

S-33 NMR chemical shifts have been determined for the first time for a seri es of 10 substituted phenacyl sulfones. Electron-withdrawing and electron-r eleasing substituents in 4-substituted phenyl-4'-methylphenacyl sulfones, p -MeC6H4COCH2SO2C6H4R-p, cause a 'reverse' substituent effect on the S-33 NM R resonance. Dual-substituent parameter (DSP) analysis of delta(S-33) value s revealed that the inductive effect of the substituent predominates over i ts resonance effect. This finding shows that the S-33 NMR chemical shifts a re of importance in estimating the electronic properties of sulfur-containi ng compounds. The C-13 and O-17 NMR chemical shifts of the title compounds are also discussed. Copyright (C) 1999 John Wiley & Sons, Ltd.