Bulletin of the Chemical Society of Japan · 1973 · 28 citations · 11 references
Natural SciencesChemistryOrganic ChemistryPhysical ChemistrySpectroscopyChemical BondingElectronic EffectsHeterocyclic ChemistryHeterocyclic CompoundsSubstituent EffectsSulfur ChemistryAromatic Electronic EffectsHammett AnalysisHammett Electronic EffectsPhenyl Ring Substitution EffectsRing Sulfur SubstitutionSulfur Containing Organic CompoundsTransmission EffectsTransmission Efficiency
Abstract The 13C chemical shifts of ring-substituted phenyl vinyl ethers and sulfides were measured and discussed in relation to the change in electron distribution caused by the ring-substitution. The Hammett plots of the shifts for the terminal carbon confirm the greater transmission efficiency of sulfur atom. An “inverse” substituent effect was found for the α-carbon of both compounds. This suggests that the bond-polarization plays an important role in the transmission of electronic effect.
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