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The behaviour of α-benzyl-α-bromo-malononitrile (BBMD) as oxidizing agent was characterized. The dependence of the electrochemical reduction potentials of BBMD on the pH-values of the solutions was examined. BBMD is reduced in a two-electron wave with half-wave potentials between + 230 and + 312 mV vs. Ag/AgCl/Cl - . BBMD is able to oxidize different organic compounds with OH-, SH-, NH- and CH- groups as well as a series of biological reducing agents as ubihydroquinone, plastohydroquinone, dihydro-lipoic acid, FADH 2 , NADPH and NADH. In all these cases BBMD is reduced to benzylmalononitrile. Kinetic investigations of this reduction process using NADH as reducing agent and also NMR-investigations using deuterated NADH-models showed that BBMD is directly reduced to benzylmalononitrile without producing benzylidenemalononitrile as intermediate. The reduction of BBMD with reduced pyridine nucleotides as well as that of benzylidene­ malononitrile were accelerated by an enzyme which was concentrated from human erythrocytes, using 2-chloro-benzylidenemalononitrile (CS) as substrate.

zeitschrift für naturforschung c

Chemische und biochemische Charakterisierung von α-Benzyl-α-brommalonitril (BBMD) als Oxidationsmittel / Chemical and Biochemical Characterization of α-Benzyl-α-bromo-malononitrile (BBMD) as Oxidizing Agent