5-Phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride

The new triazole-functionalized phospho­nic acid 5-phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride, C(10)H(13)N(3)O(3)P(+)·Cl(−) (PTEPHCl), was synthesized by the ‘click’ reaction of the alkyl azide diethyl-(2-azido­eth­yl)phospho­nate with phenyl­acetyl­ene to give the dieth­yl[2-(4-phen...

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Autores principales: Chachlaki, Elpiniki, Choquesillo-Lazarte, Duane, Demadis, Konstantinos D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2022
Materias:
Data Reports
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9462002/
https://www.ncbi.nlm.nih.gov/pubmed/36340873
http://dx.doi.org/10.1107/S2414314622001894
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author Chachlaki, Elpiniki
Choquesillo-Lazarte, Duane
Demadis, Konstantinos D.
author_facet Chachlaki, Elpiniki
Choquesillo-Lazarte, Duane
Demadis, Konstantinos D.
author_sort Chachlaki, Elpiniki
collection PubMed
description The new triazole-functionalized phospho­nic acid 5-phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride, C(10)H(13)N(3)O(3)P(+)·Cl(−) (PTEPHCl), was synthesized by the ‘click’ reaction of the alkyl azide diethyl-(2-azido­eth­yl)phospho­nate with phenyl­acetyl­ene to give the dieth­yl[2-(4-phenyl-1H-1,2,3-triazol-1-yl)eth­yl]phospho­nate ester, which was then hydrolyzed under acidic conditions (HCl) to give the ‘free’ phospho­nic acid. The use of HCl for the hydrolysis caused protonation of the triazole ring, rendering the compound cationic, charged-balanced by a Cl(−) anion. There are extensive hydrogen-bonding inter­actions in the structure of PTEPHCl, involving the phospho­nic acid (–PO(3)H(2)) group, the triazolium ring and the Cl(−) anion. [Image: see text]
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spelling pubmed-94620022022-11-04 5-Phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride Chachlaki, Elpiniki Choquesillo-Lazarte, Duane Demadis, Konstantinos D. IUCrdata Data Reports The new triazole-functionalized phospho­nic acid 5-phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride, C(10)H(13)N(3)O(3)P(+)·Cl(−) (PTEPHCl), was synthesized by the ‘click’ reaction of the alkyl azide diethyl-(2-azido­eth­yl)phospho­nate with phenyl­acetyl­ene to give the dieth­yl[2-(4-phenyl-1H-1,2,3-triazol-1-yl)eth­yl]phospho­nate ester, which was then hydrolyzed under acidic conditions (HCl) to give the ‘free’ phospho­nic acid. The use of HCl for the hydrolysis caused protonation of the triazole ring, rendering the compound cationic, charged-balanced by a Cl(−) anion. There are extensive hydrogen-bonding inter­actions in the structure of PTEPHCl, involving the phospho­nic acid (–PO(3)H(2)) group, the triazolium ring and the Cl(−) anion. [Image: see text] International Union of Crystallography 2022-02-25 /pmc/articles/PMC9462002/ /pubmed/36340873 http://dx.doi.org/10.1107/S2414314622001894 Text en © Chachlaki et al. 2022 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Data Reports
Chachlaki, Elpiniki
Choquesillo-Lazarte, Duane
Demadis, Konstantinos D.
5-Phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride
title 5-Phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride
title_full 5-Phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride
title_fullStr 5-Phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride
title_full_unstemmed 5-Phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride
title_short 5-Phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride
title_sort 5-phenyl-3-(2-phosphono­eth­yl)-1,2,3-triazol-1-ium chloride
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9462002/
https://www.ncbi.nlm.nih.gov/pubmed/36340873
http://dx.doi.org/10.1107/S2414314622001894
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