INTERACTIONS BETWEEN FUNCTIONAL-GROUPS .4. THE RESPONSES OF 4 DIAZONIUM GROUPS TO ADJACENT ELECTRON-RICH ATOMS IN PERI-SUBSTITUTED NAPHTHALENE AND QUINOLINE DERIVATIVES

Four peri-substituted naphthalene-1-diazonium cations all show short a ttractive interactions between an electron-rich atom of the peri-subst ituent and the alpha-N-atom of the diazonium group. These are interpre ted as models for incipient nucleophilic attack on a N=N bond. The dia zonium group is a better acceptor of electron density 'through space' than the NO2 group, which parallels their relative 'through-sigma-bond ' inductive effects.