We investigate the kinetics of bromination of malonic acid, bromomalonic acid, tartronic acid, and
ethanetetracarboxylic acid in 1 M sulfuric acid with bromine and hypobromous acid as brominating agents.
In all cases the reaction occurs via the enol form of the acid, and the reaction products are brominated species.
The possibility of bromide production in the reaction of malonic acid or bromomalonic acid with hypobromous
acid can be ruled out. These results are important for the negative feedback loop in the Belousov−Zhabotinsky
reaction.
Applying combined HPLC and NMR techniques, it was found that,
besides the already known 1,1,2,2-ethanetetracarboxylic acid (ETA), monomalonyl malonate (MAMA) is also a
product of the Ce4+−malonic
acid reaction. This is indirect evidence that two different types
of organic radicals are formed in the
reaction: the alkyl and the carboxylato malonyl radicals. While
ETA is a recombination product of two
alkyl radicals, MAMA is formed in the recombination of one alkyl and
one carboxylato radical.
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