Artículo
Study of the electrochemical betanidin oxidation path using computational methods
Fecha de publicación:
07/2022
Editorial:
Royal Society of Chemistry
Revista:
Physical Chemistry Chemical Physics
ISSN:
1463-9076
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
Betalains can be used in the food, drug, and cosmetic industries and have shown their bioactive potential. For these reasons, unraveling their oxidation mechanism is of high importance and demands a systematic and multidisciplinary study. Moreover, the properties mentioned above are drastically influenced by pH and other physicochemical conditions. Betanidin (1) is a relevant molecule of this family and is crucial to elucidating the oxidation mechanism in which its pigment is involved. In the present study, the pKas and oxidation potential values for all protic groups of 1 were analyzed using B3LYP/6-31+G(d,p)/SMD as the computational methodology. Moreover, six explicit water molecules were added to improve the solvation-free energy values. The oxidation mechanism at each pH was constructed and analyzed in depth. On the other hand, cyclic voltammetry simulations allowed obtaining electrochemical data from experiments and support the proposed mechanism. In the present work, the main oxidation path of 1 is described and consists of a concerted electron-proton transfer followed by a sequential electron and proton transfer to obtain the o-quinone product or a quinone methide molecule.
Palabras clave:
BETALAINS
,
PKA CALCULATION
,
OXIDATION POTENTIAL
,
EXPLICIT WATER MOLECULES
,
SMD
Archivos asociados
Licencia
Identificadores
Colecciones
Articulos(CCT - NOA SUR)
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - NOA SUR
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - NOA SUR
Articulos(IFEG)
Articulos de INST.DE FISICA ENRIQUE GAVIOLA
Articulos de INST.DE FISICA ENRIQUE GAVIOLA
Citación
Gavilán Arriazu, Edgardo Maximiliano; Rodríguez, Sergio Antonio; Study of the electrochemical betanidin oxidation path using computational methods; Royal Society of Chemistry; Physical Chemistry Chemical Physics; 24; 32; 7-2022; 19269-19278
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