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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...

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Autores principales: Mohan, Midhun, Essalhi, Mohamed, Zaye, Sarah, Rana, Love Karan, Maris, Thierry, Duong, Adam
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
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.
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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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