Abstract
By reaction of primary carboxamides with “dibromoisocyanuric acid” (DBI) N-monobromoamides can be readily obtained as well as the N,N-dibromoamides described in an earlier paper1. Reactions, some of them new, and properties of these compounds are described and compared with those of the N,N-dibromoamides. Like other compounds bearing the NHBr group2, 3 the N-monobromocarboxamides disproportionate at room temperature according to: 2 RCONHBr ⇌ ⇋ RCONH2+RCONBr2. For CH3CONHBr the equilibrium constant was found to beK=0.02. In aqueous solution they behave as weak acids. The dissociation constants of eight compounds [R=−CH3, −C2H5, −CH2Cl, −CHCl2, −CCl3, −CF3, −C(CH3)3 and −C6H5] were measured: they differ from those of the corresponding carboxylic acids by about three powers of ten.
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Gottardi, W. N-Monobromamide: Darstellung durch Bromierung mit „Dibromisocyanursäure”, Eigenschaften. Monatshefte für Chemie 106, 611–623 (1975). https://doi.org/10.1007/BF00902165
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DOI: https://doi.org/10.1007/BF00902165