title: Effect of Molecular Interactions on Electron-Transfer and Antioxidant Activity of Bis(alkanol)selenides: A Radiation Chemical Study.
abstract: Understanding electron-transfer processes is crucial for developing organoselenium compounds as antioxidants and anti-inflammatory agents. To find new redox-active selenium antioxidants, we have investigated one-electron-transfer reactions between hydroxyl ((.) OH) radical and three bis(alkanol)selenides (SeROH) of varying alkyl chain length, using nanosecond pulse radiolysis. (.) OH radical reacts with SeROH to form radical adduct, which is converted primarily into a dimer radical cation (>Se∴Se<)(+) and α-{bis(hydroxyl alkyl)}-selenomethine radical along with a minor quantity of an intramolecularly stabilized radical cation. Some of these radicals have been subsequently converted to their corresponding selenoxide, and formaldehyde. Estimated yield of these products showed alkyl chain length dependency and correlated well with their antioxidant ability. Quantum chemical calculations suggested that compounds that formed more stable (>Se∴Se<)(+) , produced higher selenoxide and lower formaldehyde. Comparing these results with those for sulfur analogues confirmed for the first time the distinctive role of selenium in making such compounds better antioxidants.
authors.affiliation: Radiation and Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400085, India.|Homi Bhabha National Institute, Anushaktinagar, Mumbai, 400094, India.
authors.forename: Pavitra V
authors.initials: PV
authors.lastname: Kumar
authors.affiliation: Radiation and Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400085, India. beenam@barc.gov.in.
authors.forename: Beena G
authors.initials: BG
authors.lastname: Singh
authors.affiliation: Chemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400085, India.
authors.forename: Prasad P
authors.initials: PP
authors.lastname: Phadnis
authors.affiliation: Homi Bhabha National Institute, Anushaktinagar, Mumbai, 400094, India.|Chemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400085, India.
authors.forename: Vimal K
authors.initials: VK
authors.lastname: Jain
authors.affiliation: Radiation and Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400085, India. kindira@barc.gov.in.|Homi Bhabha National Institute, Anushaktinagar, Mumbai, 400094, India. kindira@barc.gov.in.
authors.forename: K Indira
authors.initials: KI
authors.lastname: Priyadarsini
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry*; D002412:Cations / Q000737:chemistry*; D004579:Electron Transport; D004583:Electrons; D017665:Hydroxyl Radical / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000737:chemistry*; D011675:Pulse Radiolysis / Q000379:methods*; D013455:Sulfur / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000975:Antioxidants; D002412:Cations; D016566:Organoselenium Compounds; D017665:Hydroxyl Radical; D013455:Sulfur
keywords: antioxidants; pulse radiolysis; radical reactions; selenides; selenoxides