http://www.cnr.it/ontology/cnr/individuo/prodotto/ID50431
The selective OH radical oxidation of Sorbitylfurfural: a Combined Experimental and Theoretical Study (Articolo in rivista)
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- Label
- The selective OH radical oxidation of Sorbitylfurfural: a Combined Experimental and Theoretical Study (Articolo in rivista) (literal)
- Anno
- 2002-01-01T00:00:00+01:00 (literal)
- Alternative label
Emmi S.S., D'Angelantonio M., Poggi G., Russo M., Beggiato G., Larsen B. (2002)
The selective OH radical oxidation of Sorbitylfurfural: a Combined Experimental and Theoretical Study
(literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Emmi S.S., D'Angelantonio M., Poggi G., Russo M., Beggiato G., Larsen B. (literal)
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- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
- Note
- ISI Web of Science (WOS) (literal)
- Titolo
- The selective OH radical oxidation of Sorbitylfurfural: a Combined Experimental and Theoretical Study (literal)
- Abstract
- Sorbitylfurfural (Furalglucitol), widely used in cosmetic industry as
antioxidant and anti-inflammatory agent, reacts with hydroxyl radical in
neutral aqueous solution with a rate constant almost at the diffusional
limit, k1 = 7.1 x 10^9 M-1s-1. Despite the unselective character of the OH
radical, addition to the 5? position in the furanic ring seems to provide
the dominant path. The consequent allylic radical undergoes the cleavage
of the C-O bond (k2 = 1.7 x 10^6 s-1) in beta position to form a pseudo-
seven-atom ring via a hydrogen bond between the attacking OH group and the
furanic oxygen. A 1,6 H-shift between the two oxygen atoms (k3 = 1.4 x
10^5 s-1) then precedes a disproportionation reaction which leads to the
final products (k4 = 2.0 x 10^7 M-1s-1). The proposed mechanism is based
on the UV-vis spectra of intermediates and final products obtained after
pulse and gamma radiolysis, on non-linear kinetic fittings of absorbance
versus time curves, on quantum-mechanical calculations of electronic
transitions and reaction enthalpies. The two most important final products
have been isolated and characterized as sorbityl-but-2-enal derivatives by
LC-MS. (literal)
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