Reactivity of aniline nucleophilic centers in reaction with formaldehyde

Abstract

The kinetics of aniline formaldehyde interaction in dilute acidic solution has been studied; quantitative estimation of reactivity of aniline nucleophilic centers has been carried out. It was shown that nucleophilic reactivity of amine group is defined by nitrogen atom base strength and aromatic ring nucleophilic reactivity is determined by the highest charge on nitrogen atom of aromatic ring and by ionization potential. It was ascertained that in neutral media formaldehyde and aniline interact in nitrogen atom with the formation of N-methylol aniline derivatives. C-methylol derivatives may be formed both in aniline formaldehyde reaction and by rearrangement from N-methylol derivatives.

Keywords

• aniline
• formaldehyde
• condensation
• aromatics
• amines
• amides