Journal of Organic Chemistry p. 1819 - 1823 (1984)
Update date:2022-08-11
Topics:
Hill, Steven V.
Longridge, Jethro L.
Williams, Andrew
The addition of anilines to dicyanamide ion in aqueous solution is shown to be general acid catalyzed.The Broensted exponent for the reaction where aniline substituent is varied and the acid is retained constant is βnuc=0.63 for acetic acid and βnuc=0.66 for oxonium ion.The Broensted exponent for varying the general acid when the aniline is kept constant is -0.54 for 4-sulfanilic acid.The data are consistent with a mechanism where neutral aniline attacks the anionic dicyanamide assisted by concerted proton transfer from the general acid to the substrate nitrogen.
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