Inductive and field effects in aromatic substitution. Part IV. The nitration of 1- and 2-phenylcyclohexylammonium ions

Abstract

The kinetics and products of nitration of certain 1-phenyl- and 2-phenyl-cyclohexylammonium ions with ⁺NMe₃ or ⁺NH₃ poles are reported for reactions in aqueous sulphuric acid. The comparison of these results with those for the ions Ph[CH₂]_n⁺NR₃(R = H or Me) is used to investigate how the meta-deactivation produced by a –C–C–⁺NR₃ substituent depends on the conformation of the carbon chain. The comparison provides evidence for a contribution from the direct electrostatic effect of the pole but suggests that other types of interaction are significant when there is only one carbon atom between the pole and the ring.