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, CHNOP·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-...
| Autores: | , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2022 |
| País: | España |
| Recursos: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/289467 |
| Acesso em linha: | http://hdl.handle.net/10261/289467 |
| Access Level: | acceso abierto |
| Palavra-chave: | Click chemistry Crystal structure Hydrogen bonding Phosphonate Triazole |
| Resumo: | The new triazole-functionalized phosphonic acid 5-phenyl-3-(2-phosphonoethyl)-1,2,3-triazol-1-ium chloride, CHNOP·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 Clanion. There are extensive hydrogen-bonding interactions in the structure of PTEPHCl, involving the phosphonic acid (-POH) group, the triazolium ring and the Clanion. |
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