Seleninic acid

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Not to be confused with selenenic acid.
Chemical structure of methaneseleninic acid

A seleninic acid is an

organoselenium compound and an oxoacid with the general formula RSeO2H, where R ≠ H. Its structure is R−Se(=O)−OH. It is a member of the family of organoselenium oxoacids, which also includes selenenic acids and selenonic acids, which are R−Se−OH and R−Se(=O)2−OH, respectively. The parent member of this family of compounds is methaneseleninic acid
(CH3−Se(=O)−OH), also known as methylseleninic acid or "MSA".

Reactions and applications in synthesis

Seleninic acids (particularly areneseleninic acids) are useful catalysts for hydrogen peroxide

thioethers, etc.; peroxyseleninic acids (R−Se(=O)−OOH) are thought to be the active oxidants.[1][2][3]

Structure, bonding, properties

Methaneseleninic acid has been characterized by X-ray crystallography.[4] The configuration about the selenium atom is pyramidal, with Se-C = 1.925(8) Å, Se-O = 1.672(7) Å, Se-OH = 1.756(7) Å, the angle OSeO = 103.0(3)°, the angle HO-Se-C = 93.5(3)°, and the angle OSeC = 101.4(3)°. The structure is isomorphous to that of methanesulfinic acid [5]

Benzeneseleninic acid (

C6H5−Se(=O)−OH) had been previously characterized by X-ray methods[6] and its optical resolution reported.[7]

References

  1. doi:10.1039/b008198l
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  2. PMID 11281784
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  3. PMID 22432805
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  4. PMID 11305255
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  5. ^ Seff, K.; Heidner, E. G.; Meyers, M.; Trueblood, K. N. "The crystal and molecular structure of methanesulfinic acid." Acta Crystallographica Section B 1969, 25, 350–354.
  6. doi:10.1107/S0365110X54002551
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  7. PMID 11443664
    .
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