A structural study of 2,4-dimethylaniline derivatives

Abstract

Crystallographic studies of nitrogen-containing small molecules aid in the elucidation of their structure–activity relationships and modes of aggregation. In this study, two previously synthesized molecules are crystallographically characterized for the first time. Reaction of 2,4-dimethylaniline with N-bromosuccinimide affords the ortho-brominated derivative 2-bromo-4,6-dimethylaniline (1; C8H10BrN), which sublimates in vacuo to afford crystals featuring hydrogen-bonded chains as well as Type I halogen–halogen interactions. Conversely, alkylation of two equivalents of 2,4-dimethylaniline with 1,2-dibromoethane affords a separable mixture of N,N′-bis(2,4-dimethylphenyl)piperazine (2; C20H26N2), which was crystallographically characterized, as well as N,N′-bis(2,4-dimethylphenyl)ethylenediamine (3).