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

Elpiniki Chachlaki; Duane Choquesillo-Lazarte; Konstantinos D Demadis

doi:10.1107/S2414314622001894

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

IUCrdata. 2022 Feb 25;7(Pt 2):x220189. doi: 10.1107/S2414314622001894. eCollection 2022 Feb.

Authors

Elpiniki Chachlaki¹, Duane Choquesillo-Lazarte², Konstantinos D Demadis¹

Affiliations

¹ Crystal Engineering, Growth and Design Laboratory, Department of Chemistry, University of Crete, Voutes Campus, Crete, GR-71003, Greece.
² Laboratorio de Estudios Cristalográficos, IACT, CSIC-Universidad de Granada, Granada-18100, Spain.

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.

Keywords: click chemistry; crystal structure; hydrogen bonding; phosphonate; triazole.

Grants and funding

Funding for this research was provided for the research project ‘Innovative Materials and Applications’ (INNOVAMAT, KA 10694) by the Special Account for Research Grants.