Synthesis, Single Crystal X Ray Diffraction and Density Functional Theory Investigations of the p-Toluene Sulphonic Acid Complex of 3,5-Diphenyl-1H-Pyrazole
Abstract
In the present investigation, a novel complex of p-toluene sulphonic acid with 3,5-diphenyl-1H-pyrazole (p-TSA/DPP) was synthesized and subsequently characterized through various experimental techniques, including IR spectroscopy, 1H-NMR, and 13C-NMR, while the structural integrity of the compound was confirmed via single crystal X-ray diffraction analysis. Pyrazole molecules are stacked on top of each other and oriented in opposite directions, forming a layered polymeric structure by hydrogen bonding with two sulphuric acids. The density functional theory (DFT) method was used to analyze the synthetic compound's geometry at the B3LYP/6-31G (d, p) level. The single crystal XRD measurements and the optimized geometric parameters produced by the DFT calculation agree well.
Keywords
3,5-Diphenyl-1H-pyrazole, p-Toluene sulphonic acid, XRD, DFT
References
- Akbaş, E. (2023). DFT investigation of adsorption of pyrimidine derivatives on graphene oxide. Journal of ata-chem, 3(2).
- Akbas, E., & Berber, I. (2005). Antibacterial and antifungal activities of new pyrazolo [3, 4-d] pyridazin derivatives. European Journal of Medicinal Chemistry, 40(4), 401-405.
- Akbas, E., Celikezen, F. C., Turkez, H., Ozdemir, O., Ruzgar, A., Ergan, E., & Sahin, E. (2017). Synthesis of the 3, 5-diphenyl-1 H-pyrazole and cytogenetic and oxidative alterations after exposure of cultured human whole blood cells. Cogent Chemistry, 3(1), 1344115.
- Ameziane El Hassani, I., Rouzi, K., Assila, H., Karrouchi, K., & Ansar, M. H. (2023). Recent advances in the synthesis of pyrazole derivatives: a review. Reactions, 4(3), 478-504.
- Becerra, D., Abonia, R., & Castillo, J. C. (2022). Recent applications of the multicomponent synthesis for bioactive pyrazole derivatives. Molecules, 27(15), 4723.
- Castillo, M. V., Rudyk, R. A., Davies, L., & Brandán, S. A. (2017). Analysis of the structure and the FT-IR and Raman spectra of 2-(4-nitrophenyl)-4H-3, 1-benzoxazin-4-one. Comparisons with the chlorinated and methylated derivatives. Journal of Molecular Structure, 1140, 2-11.
- Ebenezer, O., Shapi, M., & Tuszynski, J. A. (2022). A review of the recent development in the synthesis and biological evaluations of pyrazole derivatives. Biomedicines, 10(5), 1124.
- Faisal, M., Saeed, A., Hussain, S., Dar, P., & Larik, F. A. (2019). Recent developments in synthetic chemistry and biological activities of pyrazole derivatives. Journal of Chemical Sciences, 131, 1-30.
- Karrouchi, K., Radi, S., Ramli, Y., Taoufik, J., Mabkhot, Y. N., Al-Aizari, F. A., & Ansar, M. H. (2018). Synthesis and pharmacological activities of pyrazole derivatives: A review. Molecules, 23(1), 134.
- Khelloul, N., Toubal, K., Benhalima, N., Rahmani, R., Chouaih, A., Djafri, A., & Hamzaoui, F. (2016). Crystal structure, Hirshfeld surface analysis and computational studies of thiazolidin-4-one derivative:(Z)-5-(4-Chlorobenzylidene)-3-(2-ethoxyphenyl)-2-thioxothiazolidin-4-one. Acta Chim. Slov, 63, 619-626.
