A seleninic acid is an

organoselenium compound Organoselenium compounds (or seleno-organic) are chemical compounds containing carbon-to- selenium chemical bonds. Organoselenium chemistry is the corresponding science exploring their properties and reactivity. Selenium belongs with oxygen and su ...

and an oxoacid with the general formula , where R ≠ H. Its structure is . It is a member of the family of organoselenium oxoacids, which also includes

selenenic acid A selenenic acid is an organoselenium compound and an oxoacid with the general formula RSeOH, where R ≠ H. It is the first member of the family of organoselenium oxoacids, which also include seleninic acids and selenonic acids, which are RSeO ...

s and

selenonic acid A selenonic acid is an organoselenium compound containing the SeO3H functional group. Selenonic acids are the selenium analogs of sulfonic acids. Examples of the acid are rare. Benzeneselenonic acid is a white solid. It can be prepared by the o ...

s, which are and , respectively. The parent member of this family of compounds is methaneseleninic acid (), also known as methylseleninic acid or "MSA".

Reactions and applications in synthesis

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

epoxidation In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale ...

Baeyer–Villiger oxidation The Baeyer–Villiger oxidation is an organic reaction that forms an ester from a ketone or a lactone from a cyclic ketone, using peroxyacids or peroxides as the oxidant. The reaction is named after Adolf von Baeyer and Victor Villiger who ...

s, oxidations of

thioether In organic chemistry, an organic sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A su ...

s, etc.; peroxyseleninic acids () are thought to be the active oxidants.

Structure, bonding, properties

Methaneseleninic acid has been characterized by X-ray crystallography. 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 Benzeneseleninic acid () had been previously characterized by X-ray methods and its optical resolution reported.Toshio, S.; Watanabe, I.; Kamigata, N. "Optically active seleninic acids: optical resolution and stability." ''Angew. Chem., Int. Edn.'' 2001, 40, 2460–2462.

References

Organoselenium compounds {{organic-chemistry-stub