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Article

Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1H-pyrrolo[3,2-h]quinoline and 2-(2′-pyridyl)pyrrole

1
Faculty of Mathematics and Natural Sciences, Cardinal Stefan Wyszyński University, 01-038 Warsaw, Poland
2
Faculty of Physics, University of Warsaw, 02-093 Warsaw, Poland
3
Institute of Physical Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Liudmil Antonov
Molecules 2021, 26(13), 3802; https://doi.org/10.3390/molecules26133802
Received: 27 May 2021 / Revised: 18 June 2021 / Accepted: 19 June 2021 / Published: 22 June 2021
(This article belongs to the Special Issue Tautomerism and Proton Transfer Related Phenomena)
1H-pyrrolo[3,2-h]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). View Full-Text
Keywords: proton transfer; hydrogen bond; polymorphism; high pressure; diamond anvil cell proton transfer; hydrogen bond; polymorphism; high pressure; diamond anvil cell
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MDPI and ACS Style

Kurzydłowski, D.; Chumak, T.; Rogoża, J.; Listkowski, A. Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1H-pyrrolo[3,2-h]quinoline and 2-(2′-pyridyl)pyrrole. Molecules 2021, 26, 3802. https://doi.org/10.3390/molecules26133802

AMA Style

Kurzydłowski D, Chumak T, Rogoża J, Listkowski A. Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1H-pyrrolo[3,2-h]quinoline and 2-(2′-pyridyl)pyrrole. Molecules. 2021; 26(13):3802. https://doi.org/10.3390/molecules26133802

Chicago/Turabian Style

Kurzydłowski, Dominik, Taisiia Chumak, Jakub Rogoża, and Arkadiusz Listkowski. 2021. "Hydrogen-Bonded Cyclic Dimers at Large Compression: The Case of 1H-pyrrolo[3,2-h]quinoline and 2-(2′-pyridyl)pyrrole" Molecules 26, no. 13: 3802. https://doi.org/10.3390/molecules26133802

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