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Abstract <p>The structure is proposed of the coordination complex obtained by the reaction of 5-(1-pentyl-4-methyl-1,2,3-triazol-4-yl)-6-methyluracil (TMU) with copper(II) chloride in acetone. The complex composition is determined by the elemental analysis of [CuCl<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>(TMU)]. Seven possible structures of the complex, including different ligand coordination modes and geometric isomers, are optimized by quantum chemical computations at the density functional level (BhandhLYP/def2-SVP). Reaction centers of the TMU molecule are determined by the wave function analysis, revealing the enhanced nucleophilicity of nitrogen atoms of the triazole ring, in particular, N3′, which governs their tendency to coordination with metal. Thermodynamic stabilities of the isomers are calculated at the M06/def2-TZVP level of theory with regard to the solvent (PCM model). It enables the clarification of relative energies and populations of isomeric species. The isomer in which the copper(II) ion is coordinated exclusively to the N3′ nitrogen atom of the triazole ring with the formation of the monodentate complex is found to be most stable. The high stability of this isomer is explained by minimal steric interactions between the ligands and the favorable electron delocalization in the coordination sphere. The structure of the predicted isomer agrees with the <sup>1</sup>H and <sup>13</sup>C NMR spectroscopic data for the coordination compound isolated.</p>

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Complexation of 5-(1-pentyl-4-methyl-1,2,3-triazol-4-yl)-6-Methyluracil with Copper Chloride in Organic Solvents

  • 期刊论文

  • 发表日期：

    2026年4月1日

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  • A. A. Pyshkin,
  • E. M. Khamitov,
  • I. E. Alekhina,
  • S. P. Ivanov

摘要

Abstract

The structure is proposed of the coordination complex obtained by the reaction of 5-(1-pentyl-4-methyl-1,2,3-triazol-4-yl)-6-methyluracil (TMU) with copper(II) chloride in acetone. The complex composition is determined by the elemental analysis of [CuCl2(H2O)2(TMU)]. Seven possible structures of the complex, including different ligand coordination modes and geometric isomers, are optimized by quantum chemical computations at the density functional level (BhandhLYP/def2-SVP). Reaction centers of the TMU molecule are determined by the wave function analysis, revealing the enhanced nucleophilicity of nitrogen atoms of the triazole ring, in particular, N3′, which governs their tendency to coordination with metal. Thermodynamic stabilities of the isomers are calculated at the M06/def2-TZVP level of theory with regard to the solvent (PCM model). It enables the clarification of relative energies and populations of isomeric species. The isomer in which the copper(II) ion is coordinated exclusively to the N3′ nitrogen atom of the triazole ring with the formation of the monodentate complex is found to be most stable. The high stability of this isomer is explained by minimal steric interactions between the ligands and the favorable electron delocalization in the coordination sphere. The structure of the predicted isomer agrees with the 1H and 13C NMR spectroscopic data for the coordination compound isolated.