The kinetics and mechanisms of aromatic halogen substitution. Part XXX. Chlorination of triphenylene: linear free-energy relationships in chlorinations of some aromatic hydrocarbons

Abstract

A study of the rates of chlorination of p-xylene, m-xylene, mesitylene, triphenylene, naphthalene, and phenanthrene by molecular chlorine in acetic acid, and of the proportions and nature of the products, allows a reassessment of the applicability of linear free-energy correlations with related data for other electrophilic reactions and with theoretical parameters. Similar relationships for the reactions of acidified hypochlorous acid in aqueous dioxan with a range of hydrocarbons are also discussed.