Substituent effect of the sulphinyl group in electrophilic aromatic substitution
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 11,p. 1343-1346
- https://doi.org/10.1039/p29740001343
Abstract
Partial rate factors have been determined for molecular chlorination in nitromethane and protodesilylation in H2SO4–AcOH mixtures of methyl phenyl and diphenyl sulphoxide. The electron-activating effect observed in molecular halogenation is interpreted in terms of polarization of the sulphoxide group in the transition state, induced by the electrophilic reagent. In H2SO4–AcOH mixtures Krel for protodesilylation at the para-position of methyl phenyl sulphoxide is very low, possibly because of hydrogen bonding between the sulphinyl group and the acidic medium. For methyl phenyl sulphide, sulphoxide, and some other compounds the ground state electron densities at the para-position have been evaluated from their 13C n.m.r. spectra.Keywords
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