The
mechanism and energetics of furan decomposition via the opening
of the five-membered ring structure in dilute acid solution were investigated
using density functional Car–Parrinello molecular dynamics
combined with metadynamics simulations. Diffusion of an acidic proton
from the aqueous medium leading to the formation of a protonated furan
is found to be the rate-limiting step of the ring-opening process,
with protonation at the C<sub>α</sub> position being 7 kcal
mol<sup>–1</sup> less activated than that at the C<sub>β</sub> position. Protonation at the C<sub>α</sub> position results
in the formation of 2,5-dihydro-2-furanol or 2,3-dihydro-3-furanol
via nucleophilic attack by a solvent molecule. Subsequent protonation
of the furanols at the ring oxygen initiates the opening of the furanic
ring, leading to the formation of 4-hydroxy-2-butenal
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