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Hydrogen Bonding and Polymorphism of Amino Alcohol Salts with Quinaldinate: Structural Study

Three amino alcohols, 3-amino-1-propanol (abbreviated as 3a1pOH), 2-amino-1-butanol (2a1bOH), and 2-amino-2-methyl-1-propanol (2a2m1pOH), were reacted with quinoline-2-carboxylic acid, known as quinaldinic acid. This combination yielded three salts, (3a1pOHH)quin (1, 3a1pOHH(+) = protonated 3-amino-...

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Autores principales: Podjed, Nina, Modec, Barbara
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8839704/
https://www.ncbi.nlm.nih.gov/pubmed/35164260
http://dx.doi.org/10.3390/molecules27030996
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author Podjed, Nina
Modec, Barbara
author_facet Podjed, Nina
Modec, Barbara
author_sort Podjed, Nina
collection PubMed
description Three amino alcohols, 3-amino-1-propanol (abbreviated as 3a1pOH), 2-amino-1-butanol (2a1bOH), and 2-amino-2-methyl-1-propanol (2a2m1pOH), were reacted with quinoline-2-carboxylic acid, known as quinaldinic acid. This combination yielded three salts, (3a1pOHH)quin (1, 3a1pOHH(+) = protonated 3-amino-1-propanol, quin(−) = anion of quinaldinic acid), (2a1bOHH)quin (2, 2a1bOHH(+) = protonated 2-amino-1-butanol), and (2a2m1pOHH)quin (3, 2a2m1pOHH(+) = protonated 2-amino-2-methyl-1-propanol). The 2-amino-1-butanol and 2-amino-2-methyl-1-propanol systems produced two polymorphs each, labeled 2a/2b and 3a/3b, respectively. The compounds were characterized by X-ray structure analysis on single-crystal. The crystal structures of all consisted of protonated amino alcohols with NH(3)(+) moiety and quinaldinate anions with carboxylate moiety. The used amino alcohols contained one OH and one NH(2) functional group, both prone to participate in hydrogen bonding. Therefore, similar connectivity patterns were expected. This proved to be true to some extent as all structures contained the NH(3)(+)∙∙∙(−)OOC heterosynthon. Nevertheless, different hydrogen bonding and π∙∙∙π stacking interactions were observed, leading to distinct connectivity motifs. The largest difference in hydrogen bonding occurred between polymorphs 3a and 3b, as they had only one heterosynton in common.
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spelling pubmed-88397042022-02-13 Hydrogen Bonding and Polymorphism of Amino Alcohol Salts with Quinaldinate: Structural Study Podjed, Nina Modec, Barbara Molecules Article Three amino alcohols, 3-amino-1-propanol (abbreviated as 3a1pOH), 2-amino-1-butanol (2a1bOH), and 2-amino-2-methyl-1-propanol (2a2m1pOH), were reacted with quinoline-2-carboxylic acid, known as quinaldinic acid. This combination yielded three salts, (3a1pOHH)quin (1, 3a1pOHH(+) = protonated 3-amino-1-propanol, quin(−) = anion of quinaldinic acid), (2a1bOHH)quin (2, 2a1bOHH(+) = protonated 2-amino-1-butanol), and (2a2m1pOHH)quin (3, 2a2m1pOHH(+) = protonated 2-amino-2-methyl-1-propanol). The 2-amino-1-butanol and 2-amino-2-methyl-1-propanol systems produced two polymorphs each, labeled 2a/2b and 3a/3b, respectively. The compounds were characterized by X-ray structure analysis on single-crystal. The crystal structures of all consisted of protonated amino alcohols with NH(3)(+) moiety and quinaldinate anions with carboxylate moiety. The used amino alcohols contained one OH and one NH(2) functional group, both prone to participate in hydrogen bonding. Therefore, similar connectivity patterns were expected. This proved to be true to some extent as all structures contained the NH(3)(+)∙∙∙(−)OOC heterosynthon. Nevertheless, different hydrogen bonding and π∙∙∙π stacking interactions were observed, leading to distinct connectivity motifs. The largest difference in hydrogen bonding occurred between polymorphs 3a and 3b, as they had only one heterosynton in common. MDPI 2022-02-01 /pmc/articles/PMC8839704/ /pubmed/35164260 http://dx.doi.org/10.3390/molecules27030996 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Podjed, Nina
Modec, Barbara
Hydrogen Bonding and Polymorphism of Amino Alcohol Salts with Quinaldinate: Structural Study
title Hydrogen Bonding and Polymorphism of Amino Alcohol Salts with Quinaldinate: Structural Study
title_full Hydrogen Bonding and Polymorphism of Amino Alcohol Salts with Quinaldinate: Structural Study
title_fullStr Hydrogen Bonding and Polymorphism of Amino Alcohol Salts with Quinaldinate: Structural Study
title_full_unstemmed Hydrogen Bonding and Polymorphism of Amino Alcohol Salts with Quinaldinate: Structural Study
title_short Hydrogen Bonding and Polymorphism of Amino Alcohol Salts with Quinaldinate: Structural Study
title_sort hydrogen bonding and polymorphism of amino alcohol salts with quinaldinate: structural study
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8839704/
https://www.ncbi.nlm.nih.gov/pubmed/35164260
http://dx.doi.org/10.3390/molecules27030996
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