Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1<i>H</i>-pyrrolo[3,2-<i>h</i>]quinoline and 2-(2′-pyridyl)pyrrole
1<i>H</i>-pyrrolo[3,2-<i>h</i>]qinoline (PQ) and 2-(2′-pyridyl)pyrrole (PP) are important systems in the study of proton-transfer reactions. These molecules possess hydrogen bond donor (pyrrole) and acceptor (pyridine) groups, which leads to the formation of cyclic dimers in...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/13/3802 |
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| author | Dominik Kurzydłowski Taisiia Chumak Jakub Rogoża Arkadiusz Listkowski |
| author_facet | Dominik Kurzydłowski Taisiia Chumak Jakub Rogoża Arkadiusz Listkowski |
| author_sort | Dominik Kurzydłowski |
| collection | DOAJ |
| description | 1<i>H</i>-pyrrolo[3,2-<i>h</i>]qinoline (PQ) and 2-(2′-pyridyl)pyrrole (PP) are important systems in the study of proton-transfer reactions. These molecules possess hydrogen bond donor (pyrrole) and acceptor (pyridine) groups, which leads to the formation of cyclic dimers in their crystals. Herein, we present a joint experimental (Raman scattering) and computational (DFT modelling) study on the high-pressure behaviour of PQ and PP molecular crystals. Our results indicate that compression up to 10 GPa (100 kbar) leads to considerable strengthening of the intermolecular hydrogen bond within the cyclic dimers. However, the intramolecular N–H∙∙∙N interaction is either weakly affected by pressure, as witnessed in PQ, or weakened due to compression-induced distortions of the molecule, as was found for PP. Therefore, we propose that the compression of these systems should facilitate double proton transfer within the cyclic dimers of PQ and PP, while intramolecular transfer should either remain unaffected (for PQ) or weakened (for PP). |
| first_indexed | 2024-03-10T10:10:56Z |
| format | Article |
| id | doaj.art-af37f24802d44888b3ecf104c0cc3945 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T10:10:56Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-af37f24802d44888b3ecf104c0cc39452023-11-22T01:13:15ZengMDPI AGMolecules1420-30492021-06-012613380210.3390/molecules26133802Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1<i>H</i>-pyrrolo[3,2-<i>h</i>]quinoline and 2-(2′-pyridyl)pyrroleDominik Kurzydłowski0Taisiia Chumak1Jakub Rogoża2Arkadiusz Listkowski3Faculty of Mathematics and Natural Sciences, Cardinal Stefan Wyszyński University, 01-038 Warsaw, PolandFaculty of Mathematics and Natural Sciences, Cardinal Stefan Wyszyński University, 01-038 Warsaw, PolandFaculty of Physics, University of Warsaw, 02-093 Warsaw, PolandFaculty of Mathematics and Natural Sciences, Cardinal Stefan Wyszyński University, 01-038 Warsaw, Poland1<i>H</i>-pyrrolo[3,2-<i>h</i>]qinoline (PQ) and 2-(2′-pyridyl)pyrrole (PP) are important systems in the study of proton-transfer reactions. These molecules possess hydrogen bond donor (pyrrole) and acceptor (pyridine) groups, which leads to the formation of cyclic dimers in their crystals. Herein, we present a joint experimental (Raman scattering) and computational (DFT modelling) study on the high-pressure behaviour of PQ and PP molecular crystals. Our results indicate that compression up to 10 GPa (100 kbar) leads to considerable strengthening of the intermolecular hydrogen bond within the cyclic dimers. However, the intramolecular N–H∙∙∙N interaction is either weakly affected by pressure, as witnessed in PQ, or weakened due to compression-induced distortions of the molecule, as was found for PP. Therefore, we propose that the compression of these systems should facilitate double proton transfer within the cyclic dimers of PQ and PP, while intramolecular transfer should either remain unaffected (for PQ) or weakened (for PP).https://www.mdpi.com/1420-3049/26/13/3802proton transferhydrogen bondpolymorphismhigh pressurediamond anvil cell |
| spellingShingle | Dominik Kurzydłowski Taisiia Chumak Jakub Rogoża Arkadiusz Listkowski Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1<i>H</i>-pyrrolo[3,2-<i>h</i>]quinoline and 2-(2′-pyridyl)pyrrole Molecules proton transfer hydrogen bond polymorphism high pressure diamond anvil cell |
| title | Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1<i>H</i>-pyrrolo[3,2-<i>h</i>]quinoline and 2-(2′-pyridyl)pyrrole |
| title_full | Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1<i>H</i>-pyrrolo[3,2-<i>h</i>]quinoline and 2-(2′-pyridyl)pyrrole |
| title_fullStr | Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1<i>H</i>-pyrrolo[3,2-<i>h</i>]quinoline and 2-(2′-pyridyl)pyrrole |
| title_full_unstemmed | Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1<i>H</i>-pyrrolo[3,2-<i>h</i>]quinoline and 2-(2′-pyridyl)pyrrole |
| title_short | Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1<i>H</i>-pyrrolo[3,2-<i>h</i>]quinoline and 2-(2′-pyridyl)pyrrole |
| title_sort | hydrogen bonded cyclic dimers at large compression the case of 1 i h i pyrrolo 3 2 i h i quinoline and 2 2 pyridyl pyrrole |
| topic | proton transfer hydrogen bond polymorphism high pressure diamond anvil cell |
| url | https://www.mdpi.com/1420-3049/26/13/3802 |
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