Substituent effect of the sulphinyl group in electrophilic aromatic substitution

Autor:	Alfredo Ricci, Roberto Danieli, Andrea C. Boicelli, Angelo Mangini, Graziella Pirazzini
Rok vydání:	1974
Předmět:	chemistry.chemical_compound Nitromethane Hydrogen bond Chemistry Reagent Electrophile Substituent Halogenation Electrophilic aromatic substitution Ground state Photochemistry Medicinal chemistry
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :1343
ISSN:	1364-5471 0300-9580
DOI:	10.1039/p29740001343
Popis:	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.
Databáze:	OpenAIRE
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