Carboxylation Enhances Fragmentation of Furan upon Resonant Electron Attachment

0536327 - ÚFCH JH 2021 RIV US eng J - Journal Article
Zawadzki, Mateusz - Luxford, Thomas Frederick Murray - Kočišek, Jaroslav
Carboxylation Enhances Fragmentation of Furan upon Resonant Electron Attachment.
Journal of Physical Chemistry A. Roč. 124, č. 45 (2020), s. 9427-9435. ISSN 1089-5639. E-ISSN 1520-5215
R&D Projects: GA ČR(CZ) GA19-01159S
Institutional support: RVO:61388955
Keywords : Aromatic compounds * Carboxylation * Density functional theory
OECD category: Physical chemistry
Impact factor: 2.781, year: 2020
Method of publishing: Open access

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 pi orbitals results in transformation of the nondissociative pi(2) 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.
Permanent Link: http://hdl.handle.net/11104/0314111