Kinetics and mechanism of oxidation of N, N'-dimethylaminoiminomethanesulfinic acid by acidic bromate

The Journal of Physical Chemistry. a
Adenike Otoikhian, Reuben H Simoyi

Abstract

The major metabolites of the physiologically active compound dimethylthiourea (DMTU), dimethylaminoiminomethansesulfinic acid (DMAIMSA), and dimethylaminoiminomethanesulfonic acid (DMAIMSOA) were synthesized, and their kinetics and mechanisms of oxidation by acidic bromate and aqueous bromine was determined. The oxidation of DMAIMSA is much more facile and rapid as compared to a comparable oxidation by the same reagents of the parent compound, DMTU. The stoichiometry of the bromate-DMAIMSA reaction was determined to be 2BrO 3 (-) + 3NHCH 3(NCH 3)CSO 2H + 3H 2O --> 3SO 4 (2) (-) + 2Br (-) + 3CO(NHCH 3) 2 + 6H (+), with quantitative formation of sulfate. In excess bromate conditions, the stoichiometry was 4BrO 3 (-) + 5NHCH 3(NCH 3)CSO 2H + 3H 2O --> 5SO 4 (2) (-) + 2Br 2 + 5CO(NHCH 3) 2 + 6H (+). The direct bromine-DMAIMSA reaction gave an expected stoichiometric ratio of 2:1 with no further oxidation of product dimethylurea (DMU) by aqueous bromine. The bromine-DMAIMSA reaction was so fast that it was close to diffusion-controlled. Excess bromate conditions delivered a clock reaction behavior with the formation of bromine after an initial quiescent period. DMAIMSOA, on the other hand, was extremely inert to further oxidation in...Continue Reading

References

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Jul 19, 2005·Chemical Research in Toxicology·Adenike OtoikhianJeffrey L Petersen
Jul 13, 2006·The Journal of Physical Chemistry. a·Tabitha R ChigwadaReuben H Simoyi
Jul 13, 2006·The Journal of Physical Chemistry. a·Tabitha R Chigwada, Reuben H Simoyi

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Citations

Oct 1, 2014·Chemistry : a European Journal·Sergei V MakarovQingyu Gao
Apr 19, 2019·The Journal of Physical Chemistry. a·György CsekőAttila K Horváth
Sep 18, 2020·The Journal of Organic Chemistry·Amar Ramchandra MohiteOfer Reany

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