Synthesis, characterization, crystal structures and DFT studies of some new 1,2,4-triazole and triazolidin derivatives

Hamza M. Abosadiya, El Hassane Anouar, Salima M. Abusaadiya, Siti Aishah Hasbullah, Bohari Mohd. Yamin

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A simple efficient method for synthesis of some new 1,2,4-Triazole and Triazolidin derivatives namely, 5-(4-methoxyphenyl)-2-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (1a), (2-chlorophenyl)(3,3-dimethyl-1-phenyl-5-thioxo-1,2,4-triazolidin-4-yl)methanone (1b) and (2-iodophenyl)(3,3-dimethyl-1-phenyl-5-thioxo-1,2,4-triazolidin-4-yl)methanone (1c) have been synthesized in high yields from the reaction of carbonoyl isothiocyanate with phenyl hydrazine. The final products were characterized by FT-IR, 1H and 13C NMR spectroscopic techniques. X-ray crystallographic studies showed that 1a crystallized in triclinic crystal system with space group Pī, while both 1b and 1c crystallized in orthorhombic crystal system with space group Pna21. The asymmetric unit of 1a consists two crystallographically independent molecules, while only one molecule in asymmetric unit for both 1b and 1c compounds. All molecules possess C–H ….S intramolecular hydrogen bonds which formed a pseudo-six-membered ring. Experimental results have been confirmed by the state-of-art density functional theory (DFT) in gas and solvent phase by using five different hybrid functionals B3LYP, B3P86, CAM-B3LYP, M06-2X and PBE0 combined with 6–311++G(d, p) basis set. The experimental data are relatively well produced, and relatively good correlations are obtained between the predicted and experimental data.

Original languageEnglish
Pages (from-to)315-326
Number of pages12
JournalJournal of Molecular Structure
Volume1151
DOIs
Publication statusPublished - 5 Jan 2018

Fingerprint

Density functional theory
hydrazine
Crystal structure
Derivatives
Molecules
Thiones
Crystals
Computer aided manufacturing
Hydrogen bonds
Gases
Nuclear magnetic resonance
X rays
1,2,4-triazole
isothiocyanic acid

Keywords

  • DFT studies
  • NMR
  • Thiourea derivatives
  • Triazole and triazolidin derivatives
  • X-ray

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Synthesis, characterization, crystal structures and DFT studies of some new 1,2,4-triazole and triazolidin derivatives. / Abosadiya, Hamza M.; Anouar, El Hassane; Abusaadiya, Salima M.; Hasbullah, Siti Aishah; Mohd. Yamin, Bohari.

In: Journal of Molecular Structure, Vol. 1151, 05.01.2018, p. 315-326.

Research output: Contribution to journalArticle

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AU - Anouar, El Hassane

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AU - Hasbullah, Siti Aishah

AU - Mohd. Yamin, Bohari

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