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Carboxylation Enhances Fragmentation of Furan upon Resonant Electron Attachment
[Image: see text] We report a dissociative electron attachment study to 2-furoic acid (C(5)H(4)O(3)) 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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7667636/ https://www.ncbi.nlm.nih.gov/pubmed/33125242 http://dx.doi.org/10.1021/acs.jpca.0c07283 |
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author | Zawadzki, Mateusz Luxford, Thomas F. M. Kočišek, Jaroslav |
author_facet | Zawadzki, Mateusz Luxford, Thomas F. M. Kočišek, Jaroslav |
author_sort | Zawadzki, Mateusz |
collection | PubMed |
description | [Image: see text] We report a dissociative electron attachment study to 2-furoic acid (C(5)H(4)O(3)) 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 π(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 (C(6)H(6)O(3)) and density functional theory (DFT) calculations. |
format | Online Article Text |
id | pubmed-7667636 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-76676362020-11-17 Carboxylation Enhances Fragmentation of Furan upon Resonant Electron Attachment Zawadzki, Mateusz Luxford, Thomas F. M. Kočišek, Jaroslav J Phys Chem A [Image: see text] We report a dissociative electron attachment study to 2-furoic acid (C(5)H(4)O(3)) 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 π(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 (C(6)H(6)O(3)) and density functional theory (DFT) calculations. American Chemical Society 2020-10-30 2020-11-12 /pmc/articles/PMC7667636/ /pubmed/33125242 http://dx.doi.org/10.1021/acs.jpca.0c07283 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Zawadzki, Mateusz Luxford, Thomas F. M. Kočišek, Jaroslav Carboxylation Enhances Fragmentation of Furan upon Resonant Electron Attachment |
title | Carboxylation Enhances Fragmentation of Furan upon
Resonant Electron Attachment |
title_full | Carboxylation Enhances Fragmentation of Furan upon
Resonant Electron Attachment |
title_fullStr | Carboxylation Enhances Fragmentation of Furan upon
Resonant Electron Attachment |
title_full_unstemmed | Carboxylation Enhances Fragmentation of Furan upon
Resonant Electron Attachment |
title_short | Carboxylation Enhances Fragmentation of Furan upon
Resonant Electron Attachment |
title_sort | carboxylation enhances fragmentation of furan upon
resonant electron attachment |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7667636/ https://www.ncbi.nlm.nih.gov/pubmed/33125242 http://dx.doi.org/10.1021/acs.jpca.0c07283 |
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