Crystal structure of 4-fluoro-<i>N</i>-[2-(4-fluorobenzoyl)hydrazine-1-carbonothioyl]benzamide

Firdausiah, Syadza; Huddin, Ameera Aqeela Salleh; Hasbullah, Siti Aishah; Yamin, Bohari Mohd.; Yusoff, Siti Fairus Mohd

doi:10.1107/s1600536814015761

Cited by 3 publications

(1 citation statement)

References 6 publications

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“…Atom in molecule (AIM) results demonstrated that the N-HÁÁÁCl intramolecular hydrogen bond between the 2-Cl-phenyl ring and the amide group in the free molecule changed to an H-NÁÁÁCl interaction as a result of crystal packing [47]. The inclusion of more electronegative fluorine atoms in the benzoyl group leads to similar conformational properties and the formation of intra-molecular N-HÁÁÁF hydrogen bond is further favored [48,49].…”

Section: Conformational and Structural Propertiesmentioning

confidence: 99%

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

et al. 2016

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1-(Acyl/aroyl)-3-(substituted)thioureas are privileged architectures that have received remarkable attention of researchers in view of their variable topological aspects, binding modes and broad spectrum promising pharmacological properties. Reactivity of acyl thiourea derivatives has presented various organic transformations into other demanding scaffolds and this is an attractive strategy for synthetic chemists to access heterocyclic cores. Multiple binding sites make them flexible ligands for complexation with transition metals thus occupying a distinct position in coordination chemistry. 1-(Acyl/aroyl)-3-(substituted)thioureas have also emerged as attractive candidates in various fields such as ion sensors, corrosion inhibitors, molecular electronics, in metal extraction and in pharmaceuticals. The medicinal chemistry of this organo-sulfur framework and the derived metal complexes has witnessed fantastic progress in the current era. In continuation of our efforts to compile data on the structural aspects and numerous applications of 1-(acyl/aroyl)-3-(substituted)thiourea analogs, continuous advances have prompted us to present an overview of the last 2 years literature on this exciting family of compounds through this review article.

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Section: Conformational and Structural Propertiesmentioning

confidence: 99%

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

et al. 2016

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Synthesis, characterization and antioxidant study of N,N’-bis(2-chlorobenzamidothiocarbonyl)hydrazine

Firdausiah¹,

Hasbullah²,

Yamin³

2015

AIP Conference Proceedings

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The role of acetone solvent in the reaction of 3-chloropropionyl- and 2-chloropropionyl-isothiocyanate with hydrazine

Firdausiah

Hasbullah²,

Yamin³

2019

J. Phys.: Conf. Ser.

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The reaction of 3-chloropropionylisothiocyanate with hydrazine did not give the expected bis(3-chloropropionylthioureido)hydrazine but instead 3-Chloro-N-[5,5-dimethyl-4-(4-oxo-5,6-dihydro-4H-[1,3]thiazin-2-yl)-4,5- dihydro-[1,3,4]thiadiazol-2-yl]-propionamide 2 was obtained with 23.56% yield. On the other hand 2-thiocyanatopropionylisothiocyanate undergoes crisscross cycloaddition leading to the formation of 3,3,7,7-Tetramethyl-tetrahydro-[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithione 1 with 96.1% yield. The mechanisms involving the acetone solvent for both reactions are discussed. Both compounds were evaluated to their antioxidant activity using DPPH radical scavenging method. The results shows that compound 2 with EC50 > 1000 μM is less active than 1 (EC50 of 76 μM) may be due to the S-alkylated on the structure which eliminated its activity. Compound 1 showed higher activity than ascorbic acid (EC50 of 561.36 μM) so that it is potential as antioxidant agent.

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Crystal structure of 4-fluoro-N-[2-(4-fluorobenzoyl)hydrazine-1-carbonothioyl]benzamide

Cited by 3 publications

References 6 publications

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

Synthesis, characterization and antioxidant study of N,N’-bis(2-chlorobenzamidothiocarbonyl)hydrazine

The role of acetone solvent in the reaction of 3-chloropropionyl- and 2-chloropropionyl-isothiocyanate with hydrazine

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