84802-79-9Relevant academic research and scientific papers
Kinetic and equilibrium studies of the ambident reactivity of aniline, and some derivatives, towards 4,6-dinitrobenzofuroxan
Crampton, Michael R.,Rabbitt, Lynsey C.
, p. 1669 - 1674 (2007/10/03)
The reactions of aniline and its derivatives at the 7-position of 4,6-dinitrobenzofuroxan (DNBF) may result in rapid reaction via the nitrogen centre to give anionic σ-adducts. Equilibrium constants for these reactions in DMSO are reported and correlate with pKa values of the corresponding anilinium ions. Slower reactions are observed involving electrophilic substitution by DNBF at ring-carbon atoms of the aniline derivatives; rate constants are reported. These reactions produce zwitterionic carbon-bonded σ-adducts which, in the presence of excess aniline, are in rapid equilibrium with deprotonated forms. Equilibrium constants for this acid-base process have been measured and indicate that the negatively charged DNBF moiety is electron withdrawing relative to hydrogen.
