Abstract
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.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
