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Forming Bonds While Breaking Old Ones : Isomer-Dependent Formation of H3O+ from Aminobenzoic Acid During X-ray-Induced Fragmentation

Abid, Abdul Rahman ; Veteläinen, Onni ; Boudjemia, Nacer ; Pelimanni, Eetu ; Kivimäki, Antti LU ; Alatalo, Matti ; Huttula, Marko ; Björneholm, Olle LU and Patanen, Minna (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
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organization
publishing date
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
  • scopus:85147882146
  • pmid:36749682
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
2024-06-27 16:20:21
@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}},
}