The role of intramolecular hydrogen bonding in photoelectron circular dichroism: the diastereoisomers of 1-amino-2-indanol
(1<i>R</i>,2<i>R</i>)-<i>trans</i>-Aminoindanol and (1<i>S</i>,2<i>R</i>)-<i>cis</i>-aminoindanol, denoted as <i>trans</i>-AI and <i>cis</i>-AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in <i>cis</i>-AI, which is absent in <i>trans</i>-AI. They also differ by the number of conformers under supersonic jet conditions, one for <i>trans</i>-AI and two for <i>cis</i>-AI. One-photon and resonance-enhanced two-photon photoelectron circular dichroism (PECD) spectra are obtained for the two molecules. One-photon ionisation above 11 eV results in molecular fragmentation, with very similar fragmentation pathways for <i>trans</i>-AI and <i>cis</i>-AI. Identical PECD spectra for different fragments allow associating them with reactions occurring from the same parent ion within the same electronic state. The shape of the PECD spectra is sensitive to configuration, conformation, and intramolecular hydrogen bonding. Two-photon PECD, being conformer specific, shows that the PECDs of the two ring-puckering conformers of <i>cis</i>-AI have identical signs but different values.
Authors
- Valéria Lepère (ORCID: https://orcid.org/0000-0001-5955-4372)
- Julien Vincent (ORCID: https://orcid.org/0009-0001-6491-6849)
- Jennifer Dupont
- Sebastian Hartweg (ORCID: https://orcid.org/0000-0002-3053-683X)
- Laurent Nahon (ORCID: https://orcid.org/0000-0001-9898-5693)
- Anne Zehnacker (ORCID: https://orcid.org/0000-0001-5540-0667)
- Etienne Rouquet (ORCID: https://orcid.org/0009-0003-5772-8545)
- Gustavo A. García (ORCID: https://orcid.org/0000-0003-2915-2553)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Université Paris-Saclay (FR)
- Synchrotron soleil (FR)
- Institut des Sciences Moléculaires d'Orsay (FR)
Publication Details
- Journal
- Physical Chemistry Chemical Physics
- Published
- 2024-12-26
- DOI
- https://doi.org/10.1039/d4cp04248d
- Citations
- 2
- Primary Topic
- Advanced Chemical Physics Studies
- Type
- article
- Field-Weighted Citation Impact
- 0.68
Funders
- Agence Nationale de la Recherche
- Université Paris-Saclay
- Laboratoire d’excellence Physique Atomes Lumière Matière