title: Mechanism of a redox coupling of seleninic acid with thiol.
abstract: Equimolar quantities of 2-ethoxyethaneseleninic acid and p-thiocresol react rapidly in dichloromethane solution to give the selenosulfide along with disulfide, diselenide, and two products oxidized at sulfur, the thiosulfonate and the selenosulfonate. The latter two are new for this sort of coupling; their formation may be the result of an early thioseleninate to selenosulfinate isomerization. A radical chain mechanism is proposed to account for all five products, as well as their relative amounts.
authors.affiliation: Department of Chemistry & Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA.
authors.forename: Mohannad
authors.initials: M
authors.lastname: Abdo
authors.forename: Spencer
authors.initials: S
authors.lastname: Knapp
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013441:Sulfinic Acids / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D016566:Organoselenium Compounds; D013438:Sulfhydryl Compounds; D013441:Sulfinic Acids; C473453:seleninic acid; C100040:thiosulfinic acids