The role of intramolecular hydrogen bonding in photoelectron circular dichroism: the diastereoisomers of 1-amino-2-indanol
(1 ,2 )- -Aminoindanol and (1 ,2 )- -aminoindanol, denoted as -AI and -AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in -AI, which is absent in -AI. They also differ by the number of conformers under supersonic jet conditions, one for...
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| Veröffentlicht in: | Physical chemistry chemical physics : PCCP 2025-01, Vol.27 (5), p.2739-2748 |
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| container_title | Physical chemistry chemical physics : PCCP |
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| creator | Rouquet, Etienne Dupont, Jennifer Vincent, Julien Lepère, Valéria Zehnacker, Anne Hartweg, Sebastian Garcia, Gustavo A Nahon, Laurent |
| description | (1
,2
)-
-Aminoindanol and (1
,2
)-
-aminoindanol, denoted as
-AI and
-AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in
-AI, which is absent in
-AI. They also differ by the number of conformers under supersonic jet conditions, one for
-AI and two for
-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
-AI and
-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
-AI have identical signs but different values. |
| doi_str_mv | 10.1039/d4cp04248d |
| format | Article |
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,2
)-
-Aminoindanol and (1
,2
)-
-aminoindanol, denoted as
-AI and
-AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in
-AI, which is absent in
-AI. They also differ by the number of conformers under supersonic jet conditions, one for
-AI and two for
-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
-AI and
-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
-AI have identical signs but different values.</description><identifier>ISSN: 1463-9076</identifier><identifier>ISSN: 1463-9084</identifier><identifier>EISSN: 1463-9084</identifier><identifier>DOI: 10.1039/d4cp04248d</identifier><identifier>PMID: 39812595</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chemical bonds ; Dichroism ; Electron states ; Fragmentation ; Hydrogen bonding ; Hydrogen bonds ; Photoelectrons ; Photons ; Spectra</subject><ispartof>Physical chemistry chemical physics : PCCP, 2025-01, Vol.27 (5), p.2739-2748</ispartof><rights>Copyright Royal Society of Chemistry 2025</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1551-283caad82291d3f330498cbede3a08c3573604b5aaf3d13c9eda6776fb7ddd293</cites><orcidid>0000-0003-2915-2553 ; 0000-0001-9898-5693 ; 0000-0001-5540-0667</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39812595$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rouquet, Etienne</creatorcontrib><creatorcontrib>Dupont, Jennifer</creatorcontrib><creatorcontrib>Vincent, Julien</creatorcontrib><creatorcontrib>Lepère, Valéria</creatorcontrib><creatorcontrib>Zehnacker, Anne</creatorcontrib><creatorcontrib>Hartweg, Sebastian</creatorcontrib><creatorcontrib>Garcia, Gustavo A</creatorcontrib><creatorcontrib>Nahon, Laurent</creatorcontrib><title>The role of intramolecular hydrogen bonding in photoelectron circular dichroism: the diastereoisomers of 1-amino-2-indanol</title><title>Physical chemistry chemical physics : PCCP</title><addtitle>Phys Chem Chem Phys</addtitle><description>(1
,2
)-
-Aminoindanol and (1
,2
)-
-aminoindanol, denoted as
-AI and
-AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in
-AI, which is absent in
-AI. They also differ by the number of conformers under supersonic jet conditions, one for
-AI and two for
-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
-AI and
-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
-AI have identical signs but different values.</description><subject>Chemical bonds</subject><subject>Dichroism</subject><subject>Electron states</subject><subject>Fragmentation</subject><subject>Hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>Photoelectrons</subject><subject>Photons</subject><subject>Spectra</subject><issn>1463-9076</issn><issn>1463-9084</issn><issn>1463-9084</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2025</creationdate><recordtype>article</recordtype><recordid>eNpdkTtPwzAUhS0EoqWw8ANQJBaEFPAzidlQy0uqBEOZI8d2GleJXexkKL8el5YOTPf16ZwrHQAuEbxDkPB7ReUaUkwLdQTGiGYk5bCgx4c-z0bgLIQVhBAxRE7BiPACYcbZGHwvGp141-rE1YmxvRddHOTQCp80G-XdUtukclYZu4z3ZN243ulI9N7ZRBq_Q5WRjXcmdA9JHwWVEaHXXseN67QPW3GUis5Yl-LUWCWsa8_BSS3aoC_2dQI-n58W09d0_v7yNn2cpxIxhlJcECmEKjDmSJGaEEh5ISutNBGwkITlJIO0YkLURCEiuVYiy_OsrnKlFOZkAm52umvvvgYd-rIzQeq2FVa7IZQk2uQYUUYjev0PXbnB2_hdpDIYf0DRbgJud5T0LgSv63LtTSf8pkSw3CZSzuj04zeRWYSv9pJD1Wl1QP8iID8vSoeP</recordid><startdate>20250115</startdate><enddate>20250115</enddate><creator>Rouquet, Etienne</creator><creator>Dupont, Jennifer</creator><creator>Vincent, Julien</creator><creator>Lepère, Valéria</creator><creator>Zehnacker, Anne</creator><creator>Hartweg, Sebastian</creator><creator>Garcia, Gustavo A</creator><creator>Nahon, Laurent</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2915-2553</orcidid><orcidid>https://orcid.org/0000-0001-9898-5693</orcidid><orcidid>https://orcid.org/0000-0001-5540-0667</orcidid></search><sort><creationdate>20250115</creationdate><title>The role of intramolecular hydrogen bonding in photoelectron circular dichroism: the diastereoisomers of 1-amino-2-indanol</title><author>Rouquet, Etienne ; Dupont, Jennifer ; Vincent, Julien ; Lepère, Valéria ; Zehnacker, Anne ; Hartweg, Sebastian ; Garcia, Gustavo A ; Nahon, Laurent</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1551-283caad82291d3f330498cbede3a08c3573604b5aaf3d13c9eda6776fb7ddd293</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2025</creationdate><topic>Chemical bonds</topic><topic>Dichroism</topic><topic>Electron states</topic><topic>Fragmentation</topic><topic>Hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>Photoelectrons</topic><topic>Photons</topic><topic>Spectra</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rouquet, Etienne</creatorcontrib><creatorcontrib>Dupont, Jennifer</creatorcontrib><creatorcontrib>Vincent, Julien</creatorcontrib><creatorcontrib>Lepère, Valéria</creatorcontrib><creatorcontrib>Zehnacker, Anne</creatorcontrib><creatorcontrib>Hartweg, Sebastian</creatorcontrib><creatorcontrib>Garcia, Gustavo A</creatorcontrib><creatorcontrib>Nahon, Laurent</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Physical chemistry chemical physics : PCCP</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rouquet, Etienne</au><au>Dupont, Jennifer</au><au>Vincent, Julien</au><au>Lepère, Valéria</au><au>Zehnacker, Anne</au><au>Hartweg, Sebastian</au><au>Garcia, Gustavo A</au><au>Nahon, Laurent</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The role of intramolecular hydrogen bonding in photoelectron circular dichroism: the diastereoisomers of 1-amino-2-indanol</atitle><jtitle>Physical chemistry chemical physics : PCCP</jtitle><addtitle>Phys Chem Chem Phys</addtitle><date>2025-01-15</date><risdate>2025</risdate><volume>27</volume><issue>5</issue><spage>2739</spage><epage>2748</epage><pages>2739-2748</pages><issn>1463-9076</issn><issn>1463-9084</issn><eissn>1463-9084</eissn><abstract>(1
,2
)-
-Aminoindanol and (1
,2
)-
-aminoindanol, denoted as
-AI and
-AI, are diastereoisomer aromatic aminoalcohols differing by the presence of a weak intramolecular hydrogen bond in
-AI, which is absent in
-AI. They also differ by the number of conformers under supersonic jet conditions, one for
-AI and two for
-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
-AI and
-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
-AI have identical signs but different values.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>39812595</pmid><doi>10.1039/d4cp04248d</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-2915-2553</orcidid><orcidid>https://orcid.org/0000-0001-9898-5693</orcidid><orcidid>https://orcid.org/0000-0001-5540-0667</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9076 |
| ispartof | Physical chemistry chemical physics : PCCP, 2025-01, Vol.27 (5), p.2739-2748 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chemical bonds Dichroism Electron states Fragmentation Hydrogen bonding Hydrogen bonds Photoelectrons Photons Spectra |
| title | The role of intramolecular hydrogen bonding in photoelectron circular dichroism: the diastereoisomers of 1-amino-2-indanol |
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