Abstract
We report a dissociative electron attachment study to 2-furoic acid (C5H4O3) isolated in a gas phase, which is a model molecule consisting of a carboxylic group and a furan ring. Dissociation of furan by low energy electrons is accessible only via electronic excited Feshbach resonances at energies of incident electrons above 5 eV. On the other hand, carboxylic acids are well-known to dissociate via attachment of electrons at subexcitation energies. Here we elucidate how the electron and proton transfer reactions induced by carboxylation influence stability of the furan ring. Overlap of the furan and carboxyl π orbitals results in transformation of the nondissociative π2 resonance of the furan ring to a dissociative resonance. The interpretation of hydrogen transfer reactions is supported by experimental studies of 3-methyl-2-furoic and 5-methyl-2-furoic acids (C6H6O3) and density functional theory (DFT) calculations.
Highlights
Electron scattering by furan-containing molecules has attracted significant attention in recent years
In addition to 2FA measurements we investigated 3-methyl2-furoic acid (3M-2FA) and 5-methyl-2-furoic acid (5M-2FA) molecules
At higher energies (M−H)− anions are formed via core excited Feshbach resonances that are not detected for 3M-2FA
Summary
Electron scattering by furan-containing molecules has attracted significant attention in recent years (e.g., refs 1−9). This is caused by a more general interest in electron interactions with biomolecular systems due to their involvement in the radiation chemistry of living tissues.[10−13] The molecular structure of furan can be considered as a building block of biomolecules, sugar and more complex structures such as nucleic acids. Several examples of chemical intramolecular mechanisms of hydrogen migration in the charged state of the furan and its substituents were observed.[30,31] substitution can affect the chemical and biochemical interaction of the ring structures.[32,33] It is interesting to study how substituion of the ring influences the interaction with low energy electrons, for 2FA with several important applications
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