Syntheses, crystal structures and intermolecular interactions of six novel pyrimidin-2-yl-substituted triaryltriazoles

Six new pyrimidin-2-yl-substituted triaryltriazoles, namely, 4-(4-R-phenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazoles [L1: R   = methoxy (OCH3); L2: R   = methyl (CH3); L3: R   = nil (H); L4: R   = bromo (Br); L5: R   = chloro (Cl); L6: R   = fluoro (F)] have been successfully synthesized with yields in the range 68.3 – 81.7%. Compounds L1 – 6 have been characterized by UV – Vis, FT – IR, 1H NMR and ESI – MS spectroscopy, and elemental analysis. In addition, the structures of L2 – 6 and the ethanol monosolvate of L2 (L2 · C2H5OH) have been determined by single-crystal X-ray diffraction. A combination of intermolecular O — H...N, C — H...O, C — H...N and C — H... π hydrogen bonds connects the components of L2 · C2H5OH into a three-dimensional (3D) framework. A combination of three intermolecular C — H...N hydrogen bonds links the molecules of L2 or L3 into two different 3D networks. Both L4 and L5 show a similar 3D net structure through two intermolecular C — H...N hydrogen bonds and one kind of C — H... π interaction. However, L6 displays a more complicated 3D net structure via three intermolecular C — H...N hydrogen bonds and one kind of C — H... π interaction. Notably, an interaction between the π -electrons and the lone-pair p-electrons of a halogen atom (Br, Cl and F) is observed in L4 – 6, which will further stabilize the 3D networks. The intermolecular interactions in L2 · C2H5OH and L2 – 6 were further investigat...

Source: Acta Crystallographica Section C - March 12, 2024 Category: Chemistry Authors: Song, H. Peng, R. Zuo, Y. Wang, T. Zhu, D. Tags: synthesis crystal structure pyrimidine triaryltriazole spectral characterization hydrogen bonding Hirshfeld surface analysis research papers Source Type: research