Synthesis, structural and vibrational properties of 1-(4-Fluorobenzoyl)-3-(isomeric fluorophenyl)thioureas

Saeed, Aamer; Erben, Mauricio F.; Shaheen, Uzma; Flörke, Ülrich

doi:10.1016/j.molstruc.2011.05.051

Cited by 27 publications

(19 citation statements)

References 57 publications

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“…The infrared spectra show very strong and rather broad absorptions at around 1535 (1538 cm À1 Raman) and 1534 cm À1 (1531 cm À1 Raman) for 1 and 2, respectively, which can be assigned to d(N2AH), in agreement with previous works [23]. The other d(N1AH) deformation mode appears at lower wavenumbers, also as medium-intensity absorptions at 1502 and 1505 cm À1 (1493 cm À1 , Raman), respectively [3,54].…”

Section: Vibrational Analysissupporting

confidence: 90%

“…Continuing our ongoing project aimed to the synthesis of 1-(acy l/aroyl)-3-(mono-substituted) thioureas [23,24], here we report the preparation and spectroscopic characterization of two closely related thioureas having the 1-(1-naphthoyl) group and 3-(2,4-di-fluoro-phenyl) (1) and 3-(3-chloro-4-fluoro-phenyl) (2) substitution. The crystal structures have been determined by single-crystal X-ray diffraction.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Saeed

Ashraf

White

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the C=O and C=S adopting a pseudo-antiperiplanar conformation. An intramolecular N-H⋯O=C hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular N-H⋯S=C and N-H⋯O=C hydrogen-bonding interactions involving the acylthiourea moiety. Compound 2 is further stabilized by π-stacking between adjacent naphthalene and phenyl rings. The thermal behavior, as well as the vibrational properties, studied by infrared and Raman spectroscopy data complemented by quantum chemical calculations at the B3PW91/6-311++G(d,p) support the formation of these intra- and intermolecular hydrogen bonds. Furthermore, the UV-Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations with the shapes of the simulated absorption spectra in good accordance with the experimental data.

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Section: Vibrational Analysissupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Saeed

Ashraf

White

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Continuing our project dedicated to the study of 1-(acyl/aroyl)-3-(monosubstituted) thioureas [25,26], in this article the preparation of the novel species 1-(2-chlorobenzoyl)thiourea is presented. It is interesting to note that although several thioureas containing the 1-(2-chlorobenzoyl) group with different degree of substitution at the second nitrogen atom have been reported [27][28][29][30][31], the non-substituted species remains unknown.…”

Section: Introductionmentioning

confidence: 99%

Intra- and intermolecular hydrogen bonding and conformation in 1-acyl thioureas: An experimental and theoretical approach on 1-(2-chlorobenzoyl)thiourea

Saeed

Khurshid

Bolte

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Instead of the expected normal carbonyl (C-O) absorption around 1710 cm -1 a medium strong band at 1665-78 cm -1 suggested a possible hydrogen bond formation between the H-atom of the NH-group and the O-atom of the carbonyl group. The effect and type of hydrogen bonding in thioureas have been excellently discussed by us in earlier reported paper [Saeed et al, 2011]. The 1 H NMR data for the synthesized disubstituted thioureas showed that the NH hydrogen resonates considerably down-field from other resonances in the spectra.…”

Section: Discussionmentioning

confidence: 72%

New 1-octanoyl-3-aryl thiourea derivatives: Solvent-free synthesis, characterization and multi-target biological activities

Larik

Saeed

Channar

et al. 2016

Bangladesh J Pharmacol

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An efficient solvent-free synthesis of a 10-member library of octanoyl linked substituted aryl thioureas was accomplished successfully. The octanoyl isothiocyanate was freshly prepared in excellent yield and purity by the reaction of potassium thiocyanate with octanoyl chloride followed by removal of potassium chloride by filtration. The reaction of the latter with a series of ten different substituted anilines by stirring at 60-65°C lead to the formation of the title compounds. The in vitro antifungal activity of newly synthesized compounds was evaluated against Aspergillus niger, A. flavus and Fusarium solani strains of pathogenic fungi. Antibacterial assay was carried out against Gram positive (Staphylococcus aureus, Micrococcus luteus) and Gram negative bacterial strains (Escherichia coli, Enterobacter aerogens). Furthermore, anti-oxidant potential and enzyme inhibition studies against α-amylase and butyryl cholinestrase were performed. The results obtained indicated moderate to excellent activities of most of the compounds whilst some derivatives showed potency higher than the standard used.Video Clips:<a href="https://www.youtube.com/v/GJ8JFPUHdo4">Antibacterial assay</a>: 2 min 16 sec<a href="https://www.youtube.com/v/1j73_wjZaOE">Enzyme inhibition</a>: 1 min 27 sec

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Synthesis, structural and vibrational properties of 1-(4-Fluorobenzoyl)-3-(isomeric fluorophenyl)thioureas

Cited by 27 publications

References 57 publications

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Intra- and intermolecular hydrogen bonding and conformation in 1-acyl thioureas: An experimental and theoretical approach on 1-(2-chlorobenzoyl)thiourea

New 1-octanoyl-3-aryl thiourea derivatives: Solvent-free synthesis, characterization and multi-target biological activities

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