On the Brønsted acid-catalyzed homogeneous hydrolysis of furans.

Furan affairs: Electronic structure calculations of the homogeneous Brønsted acid-catalyzed hydrolysis of 2,5-dimethylfuran show that proton transfer to the β-position is rate-limiting and provides support that the hydrolysis follows general acid catalysis. By means of projected Fukui indices, we show this to be the case for unsubstituted, 2-, and 2,5-substituted furans with electron-donating groups.

[1]  Paul J. Dauenhauer,et al.  A DFT study of the acid-catalyzed conversion of 2,5-dimethylfuran and ethylene to p-xylene , 2013 .

[2]  E. Hensen,et al.  Mechanism of Brønsted acid-catalyzed conversion of carbohydrates , 2012 .

[3]  Paul J. Dauenhauer,et al.  Cycloaddition of Biomass-Derived Furans for Catalytic Production of Renewable p-Xylene , 2012 .

[4]  Avelino Corma,et al.  Production of high quality diesel from cellulose and hemicellulose by the Sylvan process: catalysts and process variables , 2012 .

[5]  E. Stamhuis,et al.  Mechanism of reactions of furans I: A kinetic study of the acid‐catalyzed hydrolysis of furan and 2,5‐dimethylfuran , 2010 .

[6]  D. Truhlar,et al.  The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals , 2008 .

[7]  P. Fuentealba,et al.  A direct evaluation of regional Fukui functions in molecules , 1999 .

[8]  Robert G. Parr,et al.  Density functional approach to the frontier-electron theory of chemical reactivity , 1984 .

[9]  C. Swahn,et al.  Electrophilic Attack on the Furan Ring. Acid-Catalysed Protodedeuteriation, Protodetritiation, Deuteriodeprotonation, and Deuteriodetritiation at the alpha-Position. Hydrolytic Cleavage of the Ring. , 1973 .

[10]  S. Svensson,et al.  General Acid Catalysis in the Hydrolysis of a Furan Derivative. , 1972 .

[11]  K. Schwetlick,et al.  Über den Mechanismus der Furanhydrolyse , 1970 .

[12]  P. Nielsen,et al.  Equilibrium Protonation of a Carbon Base Prior to its Hydrolysis. The Acid-catalyzed Cleavage of the Furan Ring. , 1969 .

[13]  L. Ehrenberg,et al.  Kinetics of the Hydrolytic Cleavage of the Furan Ring. , 1967 .