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Environmental Sciences

Portland State University

Theses/Dissertations

2008

Organosulfur compounds

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Synthesis, Characterization And Reactivity Of Some Selected Organosulfur Oxo-Acids, Adenike Otoikhian Oct 2008

Synthesis, Characterization And Reactivity Of Some Selected Organosulfur Oxo-Acids, Adenike Otoikhian

Dissertations and Theses

The two major metabolites after S-Oxygenation of dimethylthiourea (N, N'-dimethylaminoiminomethanesulfinic acid (DMAIMSA) and N, N'-dimethylamino iminomethanesulfonic acid (DMAIMSOA)) were synthesized. Structural analysis by X-ray crystallography shows that DMAIMSA and DMAIMSOA exist as zwitterionic species in their solid form, with a positive charge delocalized around an sp2-hybridized carbon center flanked by two nitrogen atoms.

Kinetics and mechanistic studies on the oxidation of DMAIMSA and DMAIMSOA by acidified iodate/iodine and bromate/bromine were studied. The results reveal that DMAIMSA, unlike DMAIMSOA, is highly reactive. DMAIMSOA is very inert and unreactive in low pH environments. The difference in reactivity is attributed to …