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5-Phenyl-3-(2-phosphono-eth-yl)-1,2,3-triazol-1-ium chloride.

ABSTRACT: The new triazole-functionalized phospho-nic acid 5-phenyl-3-(2-phosphono-eth-yl)-1,2,3-triazol-1-ium chloride, C₁₀H₁₃N₃O₃P⁺·Cl^- (PTEPHCl), was synthesized by the 'click' reaction of the alkyl azide diethyl-(2-azido-eth-yl)phospho-nate with phenyl-acetyl-ene to give the dieth-yl[2-(4-phenyl-1H-1,2,3-triazol-1-yl)eth-yl]phospho-nate ester, which was then hydrolyzed under acidic conditions (HCl) to give the 'free' phospho-nic 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 inter-actions in the structure of PTEPHCl, involving the phospho-nic acid (-PO₃H₂) group, the triazolium ring and the Cl^- anion.

SUBMITTER: Chachlaki E

PROVIDER: S-EPMC9462002 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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5-Phenyl-3-(2-phosphono-eth-yl)-1,2,3-triazol-1-ium chloride.

Chachlaki Elpiniki E Choquesillo-Lazarte Duane D Demadis Konstantinos D KD

IUCrData 20220225 Pt 2

The new triazole-functionalized phospho-nic acid 5-phenyl-3-(2-phosphono-eth-yl)-1,2,3-triazol-1-ium chloride, C10H13N3O3P+·Cl- (PTEPHCl), was synthesized by the 'click' reaction of the alkyl azide diethyl-(2-azido-eth-yl)phospho-nate with phenyl-acetyl-ene to give the dieth-yl[2-(4-phenyl-1H-1,2,3-triazol-1-yl)eth-yl]phospho-nate ester, which was then hydrolyzed under acidic conditions (HCl) to give the 'free' phospho-nic ...[more]

PMID: 36340873

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