In order to produce hydroxyl radical from H2O2 you need either a photochemical homolysis or a one-electron reduction. Additionally, the reaction of OH radical with DMSO has been characterized it produces methyl radical as an intermediate. What kind of experimental approach are you considering?
In order to produce hydroxyl radical from H2O2 you need either a photochemical homolysis or a one-electron reduction. Additionally, the reaction of OH radical with DMSO has been characterized it produces methyl radical as an intermediate. What kind of experimental approach are you considering?
The mechanism of oxidation by peroxides can be quite complex. As an answer to your question, you can exclude OH radicals in the oxidation of sulfoxides to sulfones with peroxides if no methanesulfinic acid is detected. DMSO is a well-known OH radical scavenger resulting in the formation of methanesulfinic acid. (You can initiate OH radical formation from H2O2 or CH3COOOH by heating, in the presence of certain metal ions such Fe(II), Cu(I), Ti(III) or with alkaline. Some other metals like V(V)might initiate peroxi radical formation). In your case (in the absence of metals!) some peroxyacetic acid will be formed, which is stronger oxidizing agent than H2O2. You can also oxidize DMSO to sulfone with H2O2 alone without acetic acid (check with Google how). Anyway, most likely the electron rich oxygen atom near the proton in peroxyacetic acid or H2O2 will attack the nucleophile S-atom of DMSO. Electron shift of the intermediate leads then to sulfone and the reduced peroxide.
The mechanism of oxidation by peroxides can be quite complex. As an answer to your question, you can exclude OH radicals in the oxidation of sulfoxides to sulfones with peroxides if no methanesulfinic acid is detected. DMSO is a well-known OH radical scavenger resulting in the formation of methanesulfinic acid. (You can initiate OH radical formation from H2O2 or CH3COOOH by heating, in the presence of certain metal ions such Fe(II), Cu(I), Ti(III) or with alkaline. Some other metals like V(V)might initiate peroxi radical formation). In your case (in the absence of metals!) some peroxyacetic acid will be formed, which is stronger oxidizing agent than H2O2. You can also oxidize DMSO to sulfone with H2O2 alone without acetic acid (check with Google how). Anyway, most likely the electron rich oxygen atom near the proton in peroxyacetic acid or H2O2 will attack the nucleophile S-atom of DMSO. Electron shift of the intermediate leads then to sulfone and the reduced peroxide.
Before guessing and asking the question I would recommend you to read textbooks. This is a classical sulfoxidation reaction by peracids
Before guessing and asking the question I would recommend you to read textbooks. This is a classical sulfoxidation reaction by peracids
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In order to produce hydroxyl radical from H2O2 you need either a photochemical homolysis or a one-electron reduction. Additionally, the reaction of OH radical with DMSO has been characterized it produces methyl radical as an intermediate. What kind of experimental approach are you considering?
In order to produce hydroxyl radical from H2O2 you need either a photochemical homolysis or a one-electron reduction. Additionally, the reaction of OH radical with DMSO has been characterized it produces methyl radical as an intermediate. What kind of experimental approach are you considering?
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VOTE
The mechanism of oxidation by peroxides can be quite complex. As an answer to your question, you can exclude OH radicals in the oxidation of sulfoxides to sulfones with peroxides if no methanesulfinic acid is detected. DMSO is a well-known OH radical scavenger resulting in the formation of methanesulfinic acid. (You can initiate OH radical formation from H2O2 or CH3COOOH by heating, in the presence of certain metal ions such Fe(II), Cu(I), Ti(III) or with alkaline. Some other metals like V(V)might initiate peroxi radical formation). In your case (in the absence of metals!) some peroxyacetic acid will be formed, which is stronger oxidizing agent than H2O2. You can also oxidize DMSO to sulfone with H2O2 alone without acetic acid (check with Google how). Anyway, most likely the electron rich oxygen atom near the proton in peroxyacetic acid or H2O2 will attack the nucleophile S-atom of DMSO. Electron shift of the intermediate leads then to sulfone and the reduced peroxide.
The mechanism of oxidation by peroxides can be quite complex. As an answer to your question, you can exclude OH radicals in the oxidation of sulfoxides to sulfones with peroxides if no methanesulfinic acid is detected. DMSO is a well-known OH radical scavenger resulting in the formation of methanesulfinic acid. (You can initiate OH radical formation from H2O2 or CH3COOOH by heating, in the presence of certain metal ions such Fe(II), Cu(I), Ti(III) or with alkaline. Some other metals like V(V)might initiate peroxi radical formation). In your case (in the absence of metals!) some peroxyacetic acid will be formed, which is stronger oxidizing agent than H2O2. You can also oxidize DMSO to sulfone with H2O2 alone without acetic acid (check with Google how). Anyway, most likely the electron rich oxygen atom near the proton in peroxyacetic acid or H2O2 will attack the nucleophile S-atom of DMSO. Electron shift of the intermediate leads then to sulfone and the reduced peroxide.
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VOTE