67958-01-4Relevant articles and documents
Nucleophilic Substitution at a Trigonal Carbon. Part 5. Substituent Effects in the Reactions of Aromatic Acyl Bromides with Methanol in Acetonitrile
Kevill, Dennis N.,Knauss, Donald C.
, p. 307 - 312 (2007/10/02)
The kinetics of the methanolysis of benzoyl bromide and eight para- or meta-substituted derivatives in acetonitrile at 25.0 deg C can be analysed in terms of the simultaneous operation of overall second- and third-order processes.In turn, each of these processes can be analysed in terms of the simultaneous operation of two reaction channels, which are proposed to involve a carbonyl addition-elimination mechanism (favoured for electron-withdrawing substituents) and a process (SN2-SN1) proceeding through a loose SN2-type transition state.For the p-methoxybenzoyl bromide substrate, a third reaction channel is observed, but only for the overall second-order process (first-order in methanol), and this is tentatively described as involving electrophilic assistance by a methanol molecule to an ionization (SN1) pathway.