SYNTHESIS, STRUCTURE AND IR SPECTROSCOPIC STUDY OF COPPER(II) COMPLEXES WITH 2-AMINO-5- (PRENYLTHIO)-1,3,4-THIADIAZOLE
For the first time, three new copper(II) complexes - [CuL 4 Cl]Cl, [CuL 4 Br]Br, and [CuL 4 (SO 4 )] - were synthesized based on 2-
amino-5-(prenylthio)-1,3,4-thiadiazole (L) at an M:L molar ratio of 1:4. Ligand L was obtained by S-alkylation of 2-amino-5-
mercapto-1,3,4-thiadiazole with prenyl bromide. The composition of the complexes was confirmed by elemental analysis, XRF,
and SEM–EDX methods. Their structures were investigated using IR spectroscopy, TGA/DSC, and SC-XRD. The [CuL 4 Cl]Cl
complex has a tetragonal-pyramidal geometry, with coordination occurring through the N3 atom of the thiadiazole ring. The
elongation of the apical Cu···Cl and Cu···Br bonds is explained by the Jahn–Teller effect characteristic of the Cu(II) ion. DFT
calculations also confirmed the preferential coordination through the N3 atom.
1. Hemanth, K., Lakshmanan, K., Rajagopal, K. A review on biological activities: 1,3,4-thiadiazole and its derivatives // Rasayan J. Chem. -
2022. - Vol. 15, № 2. - P. 1573-1587. https://doi.org/10.31788/RJC.2022.1526443
2. Naureen, B., Miana, G. A., Shahid, K., Asghar, M., Tanveer, S., Sarwar, A. Iron(III) and zinc(II) monodentate Schiff base metal complexes:
Synthesis, characterisation and biological activities // J. Mol. Struct. - 2021. - Vol. 1231. - P. 129946.
https://doi.org/10.1016/j.molstruc.2021.129946
3. Torambetov, B. S. Kadirova, S. Recent advances in 1, 3, 4-thiadiazole-based metal complexes: coordination chemistry, crystal structures,
and biological activities. an overview of coordination chemistry with metals, ligands, complexes and applications: In Honor of Hacali
Necefoğlu’s 70th birthday, 101. Livre de Lyon, Lyon France, e-ISBN: 978-2-38236-965-4, Chapter VII, page 101-130
https://doi.org/10.5281/zenodo.17848648
4. Hangan, A. C., Turza, A., Lucaciu, R. L., Sevastre, B., Páll, E., Oprean, L. S., Borodi, G. New Cu 2+ complexes with N-sulfonamide ligands:
potential antitumor, antibacterial, and antioxidant agents // Molecules. - 2022. - Vol. 27, № 10. - P. 3338.
https://doi.org/10.3390/molecules27103338
5. Fei, B. L., Tu, S., Wei, Z., Wang, P., Qiao, C., Chen, Z. F. Optically pure chiral copper(II) complexes of rosin derivative as attractive
anticancer agents // Eur. J. Med. Chem. - 2019. - Vol. 176. - P. 17-186. https://doi.org/10.1016/j.ejmech.2019.05.030
6. Toshmurodov, T.T., Makhmudov, U.S., Elmuradov, B.Zh. et al. Selective Synthesis and Structural Behavior of 2-Butylthio-5-Amino-1,3,4-
Thiadiazoles // J. Chem. Sci.- 2017. - Vol. 7, № 3. - P. 205-212.
7. Zeer, G.M., Fomenko, O.Yu., Ledyaeva, O.N. Application of scanning electron microscopy in solving current problems of materials science
// J. Sib. Fed. Univ. Chem. - 2009. - Vol. 2, № 4. - P. 287-293.
8. Deckert, C., Bittner, D., Carrella, L.M. et al. Synthesis, Structural and Spectroscopic Characterization of Cu(II) Complexes with an
Asymmetric 1,3,4-Thiadiazole Ligand // Eur. J. Inorg. Chem. - 2016. - Vol. 11. - P. 1738–1747. https://doi.org/10.1002/ejic.201600072
9. Besleaga, I., Stepanenko, I., Petrasheuskaya, T.V. et al. Triapine analogues and their copper(II) complexes: redox activity, cytotoxicity, and
mR2 RNR inhibition // Inorg. Chem. - 2021. - Vol. 60, № 15. - P. 11297–11319. https://doi.org/10.1021/acs.inorgchem.1c01209
10. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B. — 6th ed. — Hoboken: Wiley, 2009. -408 p.
11. Nath, M., Song, X., Eng, G. Synthesis, spectral and thermal studies of organotin(IV) derivatives of 5-amino-3H-1,3,4-thiadiazole-2-thione
// Spectrochim. Acta A. - 2006. - Vol. 64, № 1. - P. 148–155. https://doi.org/10.1016/j.saa.2005.07.015
12. Laachir, A., Zine, H., Guesmi, S. et al. Unusual mixed-valence Cu(II)/Cu(I) coordination polymer based on 2,5-bis(pyridine-2-yl)-1,3,4-
thiadiazole and thiocyanate // Polyhedron. - 2021. - Vol. 209. - P. 115494. https://doi.org/10.1016/j.poly.2021.115494
13. Gapurova, L., Rakhmonova, D., Kadirova, S. Synthesis and spectroscopic study of complex compounds of Cu(II) and Zn with 5-amino-2-
mercaptobenzimidazole // Chem. Eng. Res. Des. - 2022. - Vol. 2021, № 4. - P. 14-21.
Copyright (c) 2026 «ACTA NUUz»
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
.jpg)
1.png)
