The electronic effect of the methyl and methoxyl groups : Partial rate factors for nitration of some substituted naphthalenes

Abstract

Partial rate factors with respect to benzene have been obtained for the nitration of naphthalene, 2,6-dimethylnaphthalene and 2-methoxy-6-methylnaphthalene. These results together with previously published data for 2-substituted methyl- and methoxy-naphthalene are discussed in terms of cation localization energies, calculated within the Parisher-Parr-Pople framework. For both Me and OMe substituents it is shown that a good account of the reactivity of these molecules, which cover a range of 10 6 in partial rate factors, can be given by the simple SCF-MO treatment if due allowance is taken of sigma and pi inductive, and mesomeric effects.