Aroylthioureas: new organic ionophores for heavy metal ion selective electrodes. A nuclear magnetic resonance study

Otazo-Sánchez, Elena María; Ortiz-del-Toro, Pedro; Estévez-Hernández, O.; Pérez-Marín, L.; Goicoechea, I; Beltran, A; Villagómez-Ibarra, José Roberto

doi:10.1016/s1386-1425(01)00724-7

Cited by 31 publications

(15 citation statements)

References 16 publications

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“…Finally, the m(C@S) stretching mode (thioamide band IV) of 1-acylthiourea compounds is found around in the 600-800 cm À1 range [3,4,59,60], but higher wavenumbers values (up to 1100 cm À1 ), are also reported [44,48]. These differences suggest that the m(C@S) stretching mode is very sensitive to the presence of an intermolecular interactions involving the C@S group [41], which originates an intense Raman dispersion due to the polarizability of the C@S bond [61].…”

Section: Vibrational Analysismentioning

confidence: 95%

“…Increasing attention is devoted to the structural and conformational elucidation of 1-(acyl/aroyl)-3-(mono-substituted) thiourea derivatives since these properties mostly determine the behavior http of these compounds as ionophores for ion selective electrodes [1][2][3][4] and chemosensors for naked-eye recognition of anions [5][6][7][8]. In particular, the thiourea molecule and the acceptor anion participate in hydrogen bond interactions [9], playing also an important role in terms of biological activity displayed by these compounds [10].…”

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 Analysismentioning

confidence: 95%

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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“…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. [309] When 1-(2-furoyl)-3-(1-naphthyl)thiourea was introduced into a sonogel-carbon matrix, it exhibited improved detection limits and good reproducibility toward Cd(II) ions (0.8 μg l −1 ).…”

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

194

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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“…The resonance for proton NHC=S, which bonded to thiocarbonyl and phenyl group, can be noticed at higher chemical shift compared to proton NHC=O that bonded to carbonyl and thiocarbonyl. These signals were different in terms of chemical shift due to the influences of the intramolecular hydrogen bond in the molecule [25].…”

Section: H and 13 C Nuclear Magnetic Resonance (Nmr) Analysismentioning

confidence: 98%

An Efficient Palladium-Thiourea Catalysed Heck Cross-Coupling Reaction for Molecular Electronic Interest

Khairul

Shariff

Rahamathullah

et al. 2017

MST

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The synthesis and utilization of C-C bonds formation are concerned about the key steps for the building of several conducting molecular electronics involving many asymmetric catalysts approached, which is an essential task that most researchers would ignore in preparing these materials to enhance the production yield of cross-coupling materials. Despite the enormous progress, there still remains a great demand for economic and practicable cross-coupling processes involving ultra-low catalyst loadings with high turnover numbers due to the employment of conventional metal catalyst. Thus, there has been an excessive interest to cultivate non-phosphine palladium catalysts for excellent achievement of activity, stability, and substrate tolerance which permit the coupling reactions to be conducted under mild reaction condition at ambient atmosphere. In this contribution, N-(4-nitrophenylcarbamothioyl)-N'-(4-methylbenzoyl) thiourea (LT1) and its metal complex of MLT1 featuring Pd (II) have been successfully characterised via typical spectroscopic methods namely; Infrared (IR) spectroscopy, Ultraviolet-visible (UV-Vis) spectroscopy, CHNS elemental analysis, and Nuclear Magnetic Resonance ( 1 H and 13 C NMR). In turn, catalytic studies of palladium catalyst (MLT1) were tested for its homogenous catalytic activity in Heck cross-coupling reaction. The reaction was monitored by Gas Chromatography-Flame Ionisation Detector (GC-FID). Results reveal that MLT1 exhibits 100% of conversion starting material into a cross-coupling product, which was alkene-based compound. Abstrak Palladium-Tiourea Yang Efisien Sebagai Katalis Reaksi Gandengan Silang Heck Untuk Molekul Elektronik.Sintesis dan penggunaan pembentukan ikatan C-C perlu diperhatikan sebagai langkah utama untuk membina beberapa molekul elektronik terkonduksi yang melibatkan banyak katalis-katalis asimetris, yang merupakan tugas yang sering diabaikan oleh kebanyakan peneliti dalam menyediakan bahan-bahan ini untuk meningkatkan pengeluaran hasil bahan gandengan silang. Meskipun telah banyak perkembangan dalam hal ini, masih ada permintaan yang tinggi untuk proses gandengan silang yang lebih ekonomis dan praktis yang hanya melibatkan pembekalan katalis yang sangat rendah dengan hasil perolehan yang tinggi dengan penggunaan katalis logam biasa. Oleh karena itu, terdapat banyak kepentingan untuk menghasilkan katalis paladium tanpa fosfina untuk pencapaian yang cemerlang dari segi aktivitas, kestabilan dan toleransi substrat yang membenarkan reaksi gandengan silang yang dijalankan dalam keadaan reaksi sederhana pada keadaan atmosfer tertentu. Dalam kajian ini, N-(4-nitrofenilcarbamotionil)-N'-(4-metilbenzoil) tiourea (LT1) dan kompleks logamnya yaitu MLT1 menampilkan Pd(II) telah berhasil dicirikan melalui kaidah spektroskopi yang biasa yaitu spektroskopi sinar inframerah (IR), spektroskopi Ultra-Lembayung Sinar Nampak (UV-Vis), analisis unsur CHNS dan Resonan Magnetik Nukleus ( 1 H dan 13 C NMR). Selanjutnya, tindak balas ini dipantau menggunakan Gas Chromatography-Fla...

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Aroylthioureas: new organic ionophores for heavy metal ion selective electrodes. A nuclear magnetic resonance study

Cited by 31 publications

References 16 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

An Efficient Palladium-Thiourea Catalysed Heck Cross-Coupling Reaction for Molecular Electronic Interest

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