Infrared intensities as a quantitative measure of intermolecular interactions. Part XX. The electronic nature of amino-, ammonio-, and diazonio-substituents

Abstract

Infrared intensities of series of meta-disubstituted benzenes show that the ND₃⁺ and NMe₃⁺ substituents are resonance donors. This is substantiated by the para-compounds; however, NMe₃⁺ is a polarizable group. The diazonio-group N₂⁺ is a strong acceptor substituent. The twisted NR₂ group is a resonance donor of strength comparable to CHMe₂.