New aromatic diamine monomers prepared from condensation reactions of aniline, p-chloroaniline, p-nitro aniline, p-chloro-m-nitro aniline with 4-amino-N,N-dimethylaniline (2:1) (aniline:reagent) in the presence of potassium dichromate in acidic media yielded new monomers of a highly colored violet and reddish-violet. Mechanism of the reaction of aniline with 4-amino-N,N-dimethylaniline in the presence of potassium dichromate as an oxidant is expected to proceed through nucleophilic substitution reaction, and the mechanism proceeds facilitated a nucleophilic attack of the substituted aniline ring on the -NH2 group of the reagent; through partial protonation of their -NH2 group, forming in diamine dye and their identification was confirmed by IR, 1H NMR, and CHN analyses.
Ibrahim, K. A. (2014, December 1). Synthesis and characterization of some new aromatic diamine monomers from oxidative coupling of anilines and substituted aniline with 4-amino-N,N-dimethyl aniline. Arabian Journal of Chemistry. Elsevier. https://doi.org/10.1016/j.arabjc.2010.12.029