title: Evaluation of Electronic Effects in the Solvolyses ofp-Methylphenyl andp-Chlorophenyl Chlorothionoformate Esters.
abstract: The solvolyses ofp-tolyl chlorothionoformate andp-chlorophenyl chlorothionoformate are studied in a variety of organic mixtures of widely varying nucleophilicity and ionizing power values. This solvolytic data is accumulated at 25.0 °C using the titration method. An analysis of the rate data using the extended (two-term) Grunwald-Winstein equation, and the concept of similarity of substrates based on theirl/mratios, shows the occurrence of simultaneous side-by-side addition-elimination and unimolecular SN1 mechanisms.
authors.affiliation: Department of Chemistry, Wesley College, 120 N. State Street, Dover, Delaware 19901-3875, USA.
authors.forename: Malcolm J
authors.initials: MJ
authors.lastname: D'Souza
authors.affiliation: Department of Chemistry, Wesley College, 120 N. State Street, Dover, Delaware 19901-3875, USA.
authors.forename: Olivia N
authors.initials: ON
authors.lastname: Hampton
authors.affiliation: Department of Chemistry, Wesley College, 120 N. State Street, Dover, Delaware 19901-3875, USA.
authors.forename: Brett M
authors.initials: BM
authors.lastname: Sansbury
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115-2862, USA.
authors.forename: Dennis N
authors.initials: DN
authors.lastname: Kevill
keywords: Grunwald-Winstein equation; Solvolysis; addition-elimination; ionization; p-chlorophenyl chlorothionoformate; p-tolyl (or p-methylphenyl) chlorothionoformate