Hydrogen bond interactions of coumarin-153 in molecular solvents: molecular dynamics and principal component analysis
Hydrogen bond interactions significantly affect the coumarin-153’s (C153) photophysics, including its ability to act as a donor of weak hydrogen bonds via its 14 C–H bonds and as an acceptor via its O atoms in the ester and the carbonyl groups, as well as via its F atom in the trifluoromethyl group....
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Académie des sciences
2024-10-01
|
| Series: | Comptes Rendus. Chimie |
| Subjects: | |
| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.314/ |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1825206088265367552 |
|---|---|
| author | Goloviznina, Kateryna Dudariev, Dmytro Miannay, François-Alexandre Kalugin, Oleg Koverga, Volodymyr Takamuku, Toshiyuki Vitale, Raffaele Idrissi, Abdenacer |
| author_facet | Goloviznina, Kateryna Dudariev, Dmytro Miannay, François-Alexandre Kalugin, Oleg Koverga, Volodymyr Takamuku, Toshiyuki Vitale, Raffaele Idrissi, Abdenacer |
| author_sort | Goloviznina, Kateryna |
| collection | DOAJ |
| description | Hydrogen bond interactions significantly affect the coumarin-153’s (C153) photophysics, including its ability to act as a donor of weak hydrogen bonds via its 14 C–H bonds and as an acceptor via its O atoms in the ester and the carbonyl groups, as well as via its F atom in the trifluoromethyl group. The distances between the donor atoms and their closest electronegative neighbor atom served as descriptors of the hydrogen bond interactions. These descriptors were calculated using the nearest neighbor radial distribution approach. Principal component analysis (PCA) was then performed on these distances to compare the unique structures surrounding donor bond atoms and identify patterns in the interactions between C153 and various solvent, such as acetonitrile, butyrolactone, propylene carbonate, methanol, ethanol, propanol, and butanol.Our findings demonstrate that, when C153 acts as a hydrogen bond donor, the interaction behavior of the H atoms that are close to the N atom and that of the H atom close to the trifluoromethyl F atom of C153 is substantially different. More specifically, the former H atoms interact preferentially with the hydroxyl oxygen atom of the solvent while the H$_{10}$ atom interacts preferentially with the ester oxygen atoms of propylene carbonate.Moreover, when C153 behaves as a hydrogen bond acceptor, PCA shows that the carbonyl O atom of C153 interacts preferentially with the hydroxyl H atom of the alcohols, while the F atoms mostly interact with the other ethyl and methyl H atoms of the solvent. |
| format | Article |
| id | doaj-art-7ce3d227903d4009958e2dc124c306d7 |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2024-10-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-7ce3d227903d4009958e2dc124c306d72025-02-07T13:41:22ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432024-10-0111310.5802/crchim.31410.5802/crchim.314Hydrogen bond interactions of coumarin-153 in molecular solvents: molecular dynamics and principal component analysisGoloviznina, Kateryna0https://orcid.org/0000-0001-9913-4938Dudariev, Dmytro1https://orcid.org/0000-0002-2556-8036Miannay, François-Alexandre2https://orcid.org/0000-0003-1131-8287 Kalugin, Oleg3https://orcid.org/0000-0003-3273-9259Koverga, Volodymyr4Takamuku, Toshiyuki5https://orcid.org/0000-0002-1975-5476Vitale, Raffaele6https://orcid.org/0000-0002-7497-1673Idrissi, Abdenacer7https://orcid.org/0000-0002-6924-6434Sorbonne Université, CNRS, Physicochimie des Électrolytes et Nanosystemes Interfaciaux, PHENIX, F-75005 Paris, FranceDepartment of Inorganic Chemistry, V.N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv, 61022, Ukarine; Univ. Lille, CNRS, UMR 8516 - LASIRe - Laboratoire Avancé de Spectroscopie pour les Interactions, la Réactivité et l’Environnement, F-59000 Lille, FranceUniv. Lille, CNRS, UMR 8516 - LASIRe - Laboratoire Avancé de Spectroscopie pour les Interactions, la Réactivité et l’Environnement, F-59000 Lille, FranceDepartment of Inorganic Chemistry, V.N. Karazin Kharkiv National University, Svobody sq. 4, Kharkiv, 61022, UkarineDepartment of Chemical Engineering, University of Illinois Chicago, Chicago, IL, 60608, USA; Materials Science Division, Argonne National Laboratory, Lemont, IL, 60439, USADepartment of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, JapanSorbonne Université, CNRS, Physicochimie des Électrolytes et Nanosystemes Interfaciaux, PHENIX, F-75005 Paris, FranceUniv. Lille, CNRS, UMR 8516 - LASIRe - Laboratoire Avancé de Spectroscopie pour les Interactions, la Réactivité et l’Environnement, F-59000 Lille, FranceHydrogen bond interactions significantly affect the coumarin-153’s (C153) photophysics, including its ability to act as a donor of weak hydrogen bonds via its 14 C–H bonds and as an acceptor via its O atoms in the ester and the carbonyl groups, as well as via its F atom in the trifluoromethyl group. The distances between the donor atoms and their closest electronegative neighbor atom served as descriptors of the hydrogen bond interactions. These descriptors were calculated using the nearest neighbor radial distribution approach. Principal component analysis (PCA) was then performed on these distances to compare the unique structures surrounding donor bond atoms and identify patterns in the interactions between C153 and various solvent, such as acetonitrile, butyrolactone, propylene carbonate, methanol, ethanol, propanol, and butanol.Our findings demonstrate that, when C153 acts as a hydrogen bond donor, the interaction behavior of the H atoms that are close to the N atom and that of the H atom close to the trifluoromethyl F atom of C153 is substantially different. More specifically, the former H atoms interact preferentially with the hydroxyl oxygen atom of the solvent while the H$_{10}$ atom interacts preferentially with the ester oxygen atoms of propylene carbonate.Moreover, when C153 behaves as a hydrogen bond acceptor, PCA shows that the carbonyl O atom of C153 interacts preferentially with the hydroxyl H atom of the alcohols, while the F atoms mostly interact with the other ethyl and methyl H atoms of the solvent.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.314/Coumarin-153SolvationMolecular dynamicsPhotophysicsHydrogen bond interactionsNearest neighbor radial distributionPrincipal component analysis (PCA) |
| spellingShingle | Goloviznina, Kateryna Dudariev, Dmytro Miannay, François-Alexandre Kalugin, Oleg Koverga, Volodymyr Takamuku, Toshiyuki Vitale, Raffaele Idrissi, Abdenacer Hydrogen bond interactions of coumarin-153 in molecular solvents: molecular dynamics and principal component analysis Comptes Rendus. Chimie Coumarin-153 Solvation Molecular dynamics Photophysics Hydrogen bond interactions Nearest neighbor radial distribution Principal component analysis (PCA) |
| title | Hydrogen bond interactions of coumarin-153 in molecular solvents: molecular dynamics and principal component analysis |
| title_full | Hydrogen bond interactions of coumarin-153 in molecular solvents: molecular dynamics and principal component analysis |
| title_fullStr | Hydrogen bond interactions of coumarin-153 in molecular solvents: molecular dynamics and principal component analysis |
| title_full_unstemmed | Hydrogen bond interactions of coumarin-153 in molecular solvents: molecular dynamics and principal component analysis |
| title_short | Hydrogen bond interactions of coumarin-153 in molecular solvents: molecular dynamics and principal component analysis |
| title_sort | hydrogen bond interactions of coumarin 153 in molecular solvents molecular dynamics and principal component analysis |
| topic | Coumarin-153 Solvation Molecular dynamics Photophysics Hydrogen bond interactions Nearest neighbor radial distribution Principal component analysis (PCA) |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.314/ |
| work_keys_str_mv | AT golovizninakateryna hydrogenbondinteractionsofcoumarin153inmolecularsolventsmoleculardynamicsandprincipalcomponentanalysis AT dudarievdmytro hydrogenbondinteractionsofcoumarin153inmolecularsolventsmoleculardynamicsandprincipalcomponentanalysis AT miannayfrancoisalexandre hydrogenbondinteractionsofcoumarin153inmolecularsolventsmoleculardynamicsandprincipalcomponentanalysis AT kaluginoleg hydrogenbondinteractionsofcoumarin153inmolecularsolventsmoleculardynamicsandprincipalcomponentanalysis AT kovergavolodymyr hydrogenbondinteractionsofcoumarin153inmolecularsolventsmoleculardynamicsandprincipalcomponentanalysis AT takamukutoshiyuki hydrogenbondinteractionsofcoumarin153inmolecularsolventsmoleculardynamicsandprincipalcomponentanalysis AT vitaleraffaele hydrogenbondinteractionsofcoumarin153inmolecularsolventsmoleculardynamicsandprincipalcomponentanalysis AT idrissiabdenacer hydrogenbondinteractionsofcoumarin153inmolecularsolventsmoleculardynamicsandprincipalcomponentanalysis |