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Updated: Jun 2, 2025

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
Oxidation of N,N-Dimethylhydroxylamine by Hexachloroiridate(IV)
Nootan P Bhattarai1,2, David M Stanbury1
1Dept. of Chemistry and Biochemistry, Auburn University, Auburn, Alabama 36849, United States.
Abstract:
The oxidation of (CH3)2NOH (DMH, N,N-dimethylhydroxylamine) is of interest because of the use of this reagent in actinide separations. Here, we report on the aqueous oxidation of DMH by [IrCl6]2-, a classic outer-sphere one-electron oxidant. The reaction is subject to adventitious catalysis by Fe2+ and Cu2+, and this catalysis can be suppressed with 1 mM oxalate. The uncatalyzed reaction yields [IrCl6]3- and nitrone (CH3)N(O)CH2. The rate law has two terms: one corresponding to oxidation of (CH3)2NOH and the other to oxidation of (CH3)2NO-. A mechanism is inferred in which the rate-limiting steps are electron-transfer oxidations of these two DMH forms, leading to their corresponding radicals. The nitrone arises from the oxidation of the DMH radical, (CH3)2NO·.
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