Structural features of 1-furoylthioureas 3-monosubstituted and 3,3-disubstituted: coordination to cadmium and analytical applications

Estévez-Hernández, O.; Duque, J.; Reguera, E.

doi:10.1080/17415993.2011.566926

Cited by 20 publications

(5 citation statements)

References 49 publications

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“…[9,10,306] In earlier work, Otazo-Sanchez et al [9] prepared 46 thiourea derivatives and demonstrated their potential use as ionophores for ISEs. Some of these were used as potentiometric sensors for heavy metals Pb (II), Cd(II) [263,307] and Hg(II). [308] A new approach reported recently involves the generation of new organic-inorganic hybrid materials prepared by covalently anchoring 1-furoyl thiourea on mesoporous silica, which exhibited good ability to remove Hg(II) from aqueous solutions.…”

Section: Anion Receptors and Ionophoresmentioning

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

198

123

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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.

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Section: Anion Receptors and Ionophoresmentioning

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

198

123

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“…The lowest RMSD value for bond angles was obtained at B3LYP/6-311++G(d,p) level (see Table 1) indicating that this method reproduce better the experimental structure for the title compound. 3,3-disubstitued thiourea derivatives assume a twisted conformation in the solid state, with the sulfur and oxygen atoms pointing approximately in same directions [7,20,[40][41][42]. The structure of the 1-acylthioureas 3-monosubstituted and 3,3disubstituted generally show a significant influence of intramolecular hydrogen bonding, which results in substantial differences between the preferred conformation observed for these compounds [12].…”

Section: Computational Detailsmentioning

confidence: 99%

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

et al. 2015

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1-benzyl-3-furoyl-1-phenylthiourea is a thiourea derivative synthesized and characterized by means of vibrational spectroscopy (IR and Raman) multinuclear NMR ( 1 H and 13 C) and elemental analysis. The geometrical parameters of this compound obtained from XRD studies were compared with the calculated values [B3LYP/6-311++G(d,p)] showing a good agreement. As determined by XRD analysis performed previously, the title compound exhibits the U-shape conformation with the C=O and C=S double bonds in anticlinal geometry. This conformational feature is mainly dictated by the substitution degree on the thiourea core and the ability of forming and intramolecular N-H···O=C hydrogen bond. The UV-visible absorption spectra of the compound in methanol solution were recorded and analyzed using time dependent density functional theory (TD-DFT). Molecular stability was investigated by applying the natural bond (NBO) analysis. Intermolecular interactions were evaluated by means of AIM approach. The calculated HOMO and LUMO energies show that the charge transfer occurs in the molecule. The molecular electrostatic potential map was calculated by DFT method. Non-linear optical (NLO) behavior of the title compound was investigated by determining of electric dipole moment, polarizability α, and hyperpolarizability β using B3LYP/6-311++G(d,p) approximation.

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“…In this conformation the C@O and HAN groups form a pseudo 6membered ring, favoring an intra-molecular interaction through a hydrogen bond [36]. When the formation of suitable hydrogen bond is prevented, as in 3,3-disubstituted derivatives, the anticlinal geometry, with u SCCO % 120°is preferred [37]. This conformation is also referred as ''U-shape'' and found for example in 1-furoyl-3,3disubstituted thioureas [38].…”

Section: X-ray Crystal Structurementioning

confidence: 95%

The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas

Saeed

Flörke

Erben

2014

Journal of Molecular Structure

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Structural features of 1-furoylthioureas 3-monosubstituted and 3,3-disubstituted: coordination to cadmium and analytical applications

Cited by 20 publications

References 49 publications

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

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

Structural, vibrational and electronic characterization of 1-benzyl-3-furoyl-1-phenylthiourea: an experimental and theoretical study

The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas

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