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Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium) Cations
[Image: see text] Dipyridonyl-substituted derivatives 2–4 of benzene, pyridine, and pyrazine, respectively, were synthesized to examine the ability of 2-pyridone and its protonated species to direct the self-assembly by hydrogen bonding. Structural analysis by single-crystal X-ray diffraction (SCXRD...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8717534/ https://www.ncbi.nlm.nih.gov/pubmed/34984296 http://dx.doi.org/10.1021/acsomega.1c05561 |
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author | Mohan, Midhun Essalhi, Mohamed Zaye, Sarah Rana, Love Karan Maris, Thierry Duong, Adam |
author_facet | Mohan, Midhun Essalhi, Mohamed Zaye, Sarah Rana, Love Karan Maris, Thierry Duong, Adam |
author_sort | Mohan, Midhun |
collection | PubMed |
description | [Image: see text] Dipyridonyl-substituted derivatives 2–4 of benzene, pyridine, and pyrazine, respectively, were synthesized to examine the ability of 2-pyridone and its protonated species to direct the self-assembly by hydrogen bonding. Structural analysis by single-crystal X-ray diffraction (SCXRD) of 2 and 4 in trifluoroacetic acid demonstrated that salts are formed as a result of the transfer of protons from the acid to the base (organic species) to generate a bis(hydroxypyridinium) dication. However, if no proton transfer takes place like in the case of crystals of 3 grown from DMSO/H(2)O, the self-assembly is mainly directed by the typical R(2)(2)(8) hydrogen bond motif of 2-pyridone. These results indicate that the process of converting a neutral 2-pyridonyl group into a hydroxypyridinium cation makes structure prediction difficult. Consequently, examination of proton transfer and assembly of dipyridone and its protonated species are of interest. In combination with SCXRD, Hirshfeld surface analysis (HSA) was also used to have a better understanding on the nature of intermolecular interactions within crystal structures of 2–4. The large number of F···H/H···F, H···O/O···H, H···H, and H···C/C···H contacts revealed by HSA indicates that hydrogen bonding and van der Waals interactions mainly contribute to crystal packing. |
format | Online Article Text |
id | pubmed-8717534 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-87175342022-01-03 Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium) Cations Mohan, Midhun Essalhi, Mohamed Zaye, Sarah Rana, Love Karan Maris, Thierry Duong, Adam ACS Omega [Image: see text] Dipyridonyl-substituted derivatives 2–4 of benzene, pyridine, and pyrazine, respectively, were synthesized to examine the ability of 2-pyridone and its protonated species to direct the self-assembly by hydrogen bonding. Structural analysis by single-crystal X-ray diffraction (SCXRD) of 2 and 4 in trifluoroacetic acid demonstrated that salts are formed as a result of the transfer of protons from the acid to the base (organic species) to generate a bis(hydroxypyridinium) dication. However, if no proton transfer takes place like in the case of crystals of 3 grown from DMSO/H(2)O, the self-assembly is mainly directed by the typical R(2)(2)(8) hydrogen bond motif of 2-pyridone. These results indicate that the process of converting a neutral 2-pyridonyl group into a hydroxypyridinium cation makes structure prediction difficult. Consequently, examination of proton transfer and assembly of dipyridone and its protonated species are of interest. In combination with SCXRD, Hirshfeld surface analysis (HSA) was also used to have a better understanding on the nature of intermolecular interactions within crystal structures of 2–4. The large number of F···H/H···F, H···O/O···H, H···H, and H···C/C···H contacts revealed by HSA indicates that hydrogen bonding and van der Waals interactions mainly contribute to crystal packing. American Chemical Society 2021-12-14 /pmc/articles/PMC8717534/ /pubmed/34984296 http://dx.doi.org/10.1021/acsomega.1c05561 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Mohan, Midhun Essalhi, Mohamed Zaye, Sarah Rana, Love Karan Maris, Thierry Duong, Adam Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium) Cations |
title | Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium)
Cations |
title_full | Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium)
Cations |
title_fullStr | Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium)
Cations |
title_full_unstemmed | Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium)
Cations |
title_short | Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium)
Cations |
title_sort | hydrogen bond patterns of dipyridone and bis(hydroxypyridinium)
cations |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8717534/ https://www.ncbi.nlm.nih.gov/pubmed/34984296 http://dx.doi.org/10.1021/acsomega.1c05561 |
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