Chemical Insights into the Antioxidant Mechanisms of Alkylseleno and Alkyltelluro Phenols: Periodic Relatives Behaving Differently
Por:
Marino, Tiziana, Galano, Annia, Mazzone, Gloria, Russo, Nino, Raul Alvarez-Idaboy, Juan
Publicada:
18 jun 2018
Resumen:
The possible antioxidant reaction mechanisms of recently synthesized and
tested alkylseleno (telluro) phenols have been explored using density
functional theory by considering two solvents physiologically relevant,
water and pentylethanoate (PE). In addition, the possible pathway for
the antioxidant regeneration with ascorbic acid has been investigated.
Results show that selenium and tellurium systems follow different
chemical behaviors. In particular, the alkylseleno phenol (ebselenol)
antioxidant activity is justified through a sequential proton
loss-electron-transfer mechanism in water media, whereas in PE the
hydrogen-atom transfer process is favored. In the case of the tellurium
derivative, the oxygen-transfer mechanism represents the preferential
one. Furthermore, electronic properties have been analyzed to
rationalize the different reactivity of the selenium- and
tellurium-containing systems. To confirm the results, smaller but
similar systems were also investigated. The calculated data support the
different mechanism (Se vs. Te) proposals.
Filiaciones:
Marino, Tiziana:
Univ Calabria, Dipartimento Chim & Tecnol Chim, Arcavacata Di Rende, CS, Italy
Galano, Annia:
Univ Autonoma Metropolitana Iztapalapa, Dept Quim, San Rafael Atlixco 186, Mexico City 09340, DF, Mexico
Mazzone, Gloria:
Univ Calabria, Dipartimento Chim & Tecnol Chim, Arcavacata Di Rende, CS, Italy
Russo, Nino:
Univ Calabria, Dipartimento Chim & Tecnol Chim, Arcavacata Di Rende, CS, Italy
Raul Alvarez-Idaboy, Juan:
Univ Nacl Autonoma Mexico, Fac Quim, Dept Fis & Quim Teor, Mexico City 04510, DF, Mexico
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