Forming Bonds While Breaking Old Ones : Isomer-Dependent Formation of H3O+ from Aminobenzoic Acid During X-ray-Induced Fragmentation
(2023) In Journal of Physical Chemistry A 127(6). p.1395-1401- Abstract
Intramolecular hydrogen transfer, a reaction where donor and acceptor sites of a hydrogen atom are part of the same molecule, is a ubiquitous reaction in biochemistry and organic synthesis. In this work, we report hydronium ion (H3O+) production from aminobenzoic acid (ABA) after core-level ionization with soft X-ray synchrotron radiation. The formation of H3O+ during the fragmentation requires that at least two hydrogen atoms migrate to one of the oxygen atoms within the molecule. The comparison of two structural isomers, ortho- and meta-ABA, revealed that the production of H3O+ depends strongly on the structure of the molecule, the ortho-isomer being much more prone to... (More)
Intramolecular hydrogen transfer, a reaction where donor and acceptor sites of a hydrogen atom are part of the same molecule, is a ubiquitous reaction in biochemistry and organic synthesis. In this work, we report hydronium ion (H3O+) production from aminobenzoic acid (ABA) after core-level ionization with soft X-ray synchrotron radiation. The formation of H3O+ during the fragmentation requires that at least two hydrogen atoms migrate to one of the oxygen atoms within the molecule. The comparison of two structural isomers, ortho- and meta-ABA, revealed that the production of H3O+ depends strongly on the structure of the molecule, the ortho-isomer being much more prone to produce H3O+. The isomer-dependency suggests that the amine group acts as a donor in the hydrogen transfer process. In the case of ortho-ABA, detailed H3O+ production pathways were investigated using photoelectron-photoion-photoion coincidence (PEPIPICO) spectroscopy. It was found that H3O+ can result from a direct two-body dissociation but also from sequential fragmentation processes.
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- author
- Abid, Abdul Rahman ; Veteläinen, Onni ; Boudjemia, Nacer ; Pelimanni, Eetu ; Kivimäki, Antti LU ; Alatalo, Matti ; Huttula, Marko ; Björneholm, Olle LU and Patanen, Minna
- organization
- publishing date
- 2023
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of Physical Chemistry A
- volume
- 127
- issue
- 6
- pages
- 1395 - 1401
- publisher
- The American Chemical Society (ACS)
- external identifiers
-
- pmid:36749682
- scopus:85147882146
- ISSN
- 1089-5639
- DOI
- 10.1021/acs.jpca.2c06869
- language
- English
- LU publication?
- yes
- id
- 403b0eff-007d-4040-a2f3-857a4164f413
- date added to LUP
- 2023-02-20 14:14:25
- date last changed
- 2024-09-20 00:08:11
@article{403b0eff-007d-4040-a2f3-857a4164f413, abstract = {{<p>Intramolecular hydrogen transfer, a reaction where donor and acceptor sites of a hydrogen atom are part of the same molecule, is a ubiquitous reaction in biochemistry and organic synthesis. In this work, we report hydronium ion (H<sub>3</sub>O<sup>+</sup>) production from aminobenzoic acid (ABA) after core-level ionization with soft X-ray synchrotron radiation. The formation of H<sub>3</sub>O<sup>+</sup> during the fragmentation requires that at least two hydrogen atoms migrate to one of the oxygen atoms within the molecule. The comparison of two structural isomers, ortho- and meta-ABA, revealed that the production of H<sub>3</sub>O<sup>+</sup> depends strongly on the structure of the molecule, the ortho-isomer being much more prone to produce H<sub>3</sub>O<sup>+</sup>. The isomer-dependency suggests that the amine group acts as a donor in the hydrogen transfer process. In the case of ortho-ABA, detailed H<sub>3</sub>O<sup>+</sup> production pathways were investigated using photoelectron-photoion-photoion coincidence (PEPIPICO) spectroscopy. It was found that H<sub>3</sub>O<sup>+</sup> can result from a direct two-body dissociation but also from sequential fragmentation processes.</p>}}, author = {{Abid, Abdul Rahman and Veteläinen, Onni and Boudjemia, Nacer and Pelimanni, Eetu and Kivimäki, Antti and Alatalo, Matti and Huttula, Marko and Björneholm, Olle and Patanen, Minna}}, issn = {{1089-5639}}, language = {{eng}}, number = {{6}}, pages = {{1395--1401}}, publisher = {{The American Chemical Society (ACS)}}, series = {{Journal of Physical Chemistry A}}, title = {{Forming Bonds While Breaking Old Ones : Isomer-Dependent Formation of H<sub>3</sub>O<sup>+</sup> from Aminobenzoic Acid During X-ray-Induced Fragmentation}}, url = {{http://dx.doi.org/10.1021/acs.jpca.2c06869}}, doi = {{10.1021/acs.jpca.2c06869}}, volume = {{127}}, year = {{2023}}, }