Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers

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

doi:10.1016/j.molstruc.2010.08.012

Cited by 33 publications

(21 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…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 Analysismentioning

confidence: 98%

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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…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 Analysismentioning

confidence: 98%

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

Self Cite

View full text Add to dashboard Cite

show abstract

“…As shown in Scheme 12, in this conformation the C=O and H−N groups form a pseudo-six-membered ring, favoring an intramolecular interaction through a hydrogen bond. [116,158,183] On the other hand, when the formation of a suitable hydrogen bond is prevented, as in 1-(acyl/aroyl)-3,3-(di-substituted) thiourea derivatives (R 2 , R 3 = H), the anticlinal geometry (U form) is preferred. In all of them, the torsion angle O=C−N−C adopts values from −13 • to 24 • representing near-cis conformations.…”

Section: Conformational and Structural Propertiesmentioning

confidence: 99%

“…[205] The analysis of selected isomeric species reveals that intra-and intermolecular hydrogen bonds played an essential role in determining the specific conformation around the planar thiourea moiety. [116,117,149] In the case of 1-acyl-3,3-disubstitued thioureas, the lack of a second N (3) −H donor contributes to major differences in the crystal structure, when compared with the mono-substituted analogues. In general, bifurcated C−H···O hydrogen-bond interactions are mainly found, giving rise to chains whose links are composed of alternating centrosymmetrical dimers (R 2 2 (10) and even R 2 2 (20) motifs).…”

Section: X-ray Crystal Packingmentioning

confidence: 99%

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

Saeed

Flörke

Erben

2013

Journal of Sulfur Chemistry

Self Cite

195

123

View full text Add to dashboard Cite

This review provides an overview of the chemistry, structure and potential applications of 1-(acyl/aroyl)-3-(mono-substituted) and 1-(acyl/aroyl)-3,3-(di-substituted) thioureas, with general formula R 1 C(O)N (1) HC(S)N (3) R 2 R 3 . In recent years, the title compounds have found extensive applications as ligands in coordination chemistry. The effect that nitrogen substituents exert on the intra-and intermolecular hydrogen-bonding interactions is discussed, including their role on the coordination properties displayed by these ligands. Novel applications of transition metal complexes bearing 1-(acyl/aroyl)-3-(mono-and di-substituted) thioureas are introduced. Biological aspects are also highlighted. As recently demonstrated, high-throughput screening assay and structure-activity analyses are feasible for this class of compounds. The chemical versatility of 1-(acyl)-3-(substituted) thiourea molecules and the derived metal complexes, together with the possibility of determining detailed structural properties, join biological applications in a promising interdisciplinary approach. The bibliography includes 382 references with emphasis on the literature appearing after 2007.

show abstract

“…The title 1-(4-fluorobenzoyl)-3-(isomeric fluorophenyl) thioureas were prepared using a method similar to that reported earlier for related 1-(2-chlorobenzoyl)-3-(isomeric fluorophenyl)thiourea isomers [23] in 60-84% yields (Scheme 1). Table 1 gives the elemental, mass spectrometry and NMR spectroscopic data of compounds (1-3).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

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

Saeed

Erben

Shaheen

et al. 2011

Journal of Molecular Structure

Self Cite

View full text Add to dashboard Cite

Effect of fluorine substitution on the crystal structures and vibrational properties of phenylthiourea isomers

Cited by 33 publications

References 32 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

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

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

Contact Info

Product

Resources

About