Producción Científica Profesorado

Insights on the mechanism, reactivity and selectivity of fructose and tagatose dehydration into 5-hydroxymethylfurfural: A DFT study



Mendoza Huizar, Luis Humberto

2020

Meneses-Olmedo, L.M., Cuesta Hoyos, S., Salgado Moran, G., Cardona Villada, W., Gerli Candia, L., Mendoza-Huizar, L.H. Insights on the mechanism, reactivity and selectivity of fructose and tagatose dehydration into 5-hydroxymethylfurfural: A DFT study. Computational and Theoretical Chemistry. 2020, 1190, 113009. DOI: 10.1016/j.comptc.2020.113009


Abstract


In this study, a computational DFT study was performed to propose a new acid catalyzed mechanism to produce 5HMF from d-Fructose and d-Tagatose. The reactivity and selectivity towards 5HMF formation were analyzed, and the results revealed both saccharides present higher selectivity towards 5HMF with the first dehydration occurring on oxygen 2. Fructose seems to be more reactive than tagatose, although the dehydration process of the different hydroxyl groups on tagatose produces more unstable structures, which can undergo several side reactions. The new mechanism is proposed eliminating the tautomerization step and lowering the activation free energy of the second dehydration step in 21 kcal/mol.



Producto de Investigación




Artículos relacionados

Bioacumulación y daños genotóxicos en Pez Cebra (Danio rerio) por arsénico en aguas de Zimapán, Hida...

Evaluación de Esteroides Aromáticos como Indicadores de Madurez Térmica en Extractos de Roca

The role of temperature in copper electrocrystallization in ammoniachloride solutions

Synthesis and crystal structures of cis-palladium(II) and cis-platinum(II) complexes containing di...

Electrochemical kinetic study about cobalt electrodeposition onto GCE and HOPG substrates from sulfa...

Quantum chemical study of the electrochemical reduction of the [Co(H2O)6]2+ and [Co(NH3)5(H2O)]2+ io...

Hydrogen bond studies in substituted N-(2-hydroxyphenyl)--2-[(4-methylbenzenesulfonyl)amino]acetamid...

Nucleation and growth of cobalt onto different substrates: Part I. Underpotential deposition onto a ...

Nucleation and growth of cobalt onto different substrates: Part II. The upd-opd transition onto a go...

Potentiometric behavior of graphite-epoxy electrochemical transducers towards anions, cations and pH...