A1 Journal article (refereed)
Synthesis and Characterizations of Novel Isatin-s-Triazine Hydrazone Derivatives : X-ray Structure, Hirshfeld Analysis and DFT Calculations (2023)

Al-Rasheed, H. H., AL-khamis, S. A., Barakat, A., El-Faham, A., Haukka, M., & Soliman, S. M. (2023). Synthesis and Characterizations of Novel Isatin-s-Triazine Hydrazone Derivatives : X-ray Structure, Hirshfeld Analysis and DFT Calculations. Crystals, 13(2), Article 305. https://doi.org/10.3390/cryst13020305

JYU authors or editors

Publication details

All authors or editors: Al-Rasheed, Hessa H.; AL-khamis, Sarah A.; Barakat, Assem; El-Faham, Ayman; Haukka, Matti; Soliman, Saied M.

Journal or series: Crystals

eISSN: 2073-4352

Publication year: 2023

Publication date: 12/02/2023

Volume: 13

Issue number: 2

Article number: 305

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/cryst13020305

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/85549

Abstract

A novel series of isatin-s-triazine hydrazone derivatives has been synthesized and reported herein. The synthetic methodology involved the reaction of s-triazine hydrazine precursors with isatin derivatives in the presence of CH3COOH as a catalyst and EtOH as solvent to afford the corresponding target products 6a-e in high yields and purities. The characterization data obtained from elemental analysis, FT-IR, NMR (1H- and 13C-) were in full agreement with the expected structures. Furthermore, an X-ray single crystal diffraction study of one of the target s-triazine hydrazone derivatives, 6c confirmed the structure of the desired compounds. It crystallized in the triclinic crystal system and P-1 space group with a = 10.3368(6) Å, b = 11.9804(8) Å, c = 12.7250(5) Å, α = 100.904(4)°, β = 107.959(4)° and γ = 109.638(6)°. The different non-covalent interactions which contributed in the molecular packing of 6c were analyzed using Hirshfeld analysis. The molecular packing of the organic part of the crystal structure showed important O…H (7.1%), C…H (16.4%), C…C (1.6%), H…H (34.8%), N…H (8.0%) and C…N (4.0%) interactions while for the crystal solvent, the O…H (21.3%), H…H (61.2%) and N…H (8.1%) contacts are the most significant. The studied compound 6c is polar and has a net dipole moment of 5.6072 Debye based on DFT study.

Keywords: organic chemistry; organic compounds

Free keywords: s-triazine; isatin; hydrazone derivatives; Hirshfeld; DFT; non-covalent interactions

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2023

Preliminary JUFO rating: 1