Could N-(diethylcarbamothioyl)benzamide be a good ionophore for sensor membranes?

Fraga, Ana Rosa Lazo; Destri, Giovanni Li; Forte, Giuseppe; Rescifina, Antonio; Punzo, Francesco

doi:10.1016/j.molstruc.2010.07.034

Cited by 21 publications

(9 citation statements)

References 35 publications

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“…[310] The structural and conformational properties of N-(diethylcarbamothioyl)benzamide both free and in complexes with heavy metal ions were studied and the behavior of the molecule as an ionophore and as a typical model for an ISE membrane has been simulated. [311] Based on spectroscopic data, the coordination to the metal by both the carbonyl and thiocarbonyl groups has been suggested. As already discussed, opposite orientation of the C=O and C=S groups (form S) is preferred in 1-(aroyl)-3,3-(di-substituted) thioureas, and thus an interconversion to the U form is assumed to take place upon metal coordination.…”

Section: Anion Receptors and Ionophoresmentioning

confidence: 99%

“…As already discussed, opposite orientation of the C=O and C=S groups (form S) is preferred in 1-(aroyl)-3,3-(di-substituted) thioureas, and thus an interconversion to the U form is assumed to take place upon metal coordination. In Scheme 19, the proposed mechanism is shown (adapted from [311]), from which it can be deduced that conformationally more flexible molecules are better than rigid ones as candidates for ISE ionophores.…”

Section: Anion Receptors and Ionophoresmentioning

confidence: 99%

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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%

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

View full text Add to dashboard Cite

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“…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%

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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“…3, we report the diffraction patterns of the non-activated and activated membrane, as compared with the corresponding powder diffraction pattern of the ionophore molecule alone. A detailed X-ray study of the single crystal, as well as a comparison of the single crystal results with the X-ray powder diffraction, was already performed [7,8]. The abovementioned diffraction patterns evidenced, at a glance, the disorder evolution while passing from the ionophore powder alone (in black) to the non-activated (in red) to the activated membrane (in blue), respectively.…”

Section: Xrdmentioning

confidence: 99%

“…All these sensors need a so-called conditioning-or activation-procedure, consisting of their previous contact with the sample to be checked as to get them ready to operate. In previous works [7,8], we made a first basic approach to describe the interaction mechanism of the ionophore with ions. This is what we call the molecular approach as it shed light, at the atomic level, over the interaction between the ionophore and the ions present in the sample to be measured.…”

Section: Introductionmentioning

confidence: 99%

Polymeric membranes conditioning for sensors applications: mechanism and influence on analytes detection

Fraga

Quintana

Destri

et al. 2011

J Solid State Electrochem

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In this work, we studied an ion-exchange membrane based on an inert polymer skeleton in which it is dispersed and anchored a molecule with charged groups able to discriminate and bind positive or negatively charged ions present in a sample. In order to be ready to work, electromembranes need a complex procedure called activation or conditioning. Although most of the known literature looks at the subject from an electrochemical point of view, we put forward a structural approach. Membrane conditioning, in fact, is considered a required step to improve sensor performances and to allow the collection of reproducible data. Even if this operation is carefully followed by all the operators working with sensors equipped with a membrane, it looks like that a thoroughly explanation of the working mechanism and a detailed balance of cost and gains has still not been carried out. As a consequence, we suggest a bulk or membrane approach, where the landscape is mainly characterized by the longrange structure of the membrane itself. Our findings suggest that membrane conditioning has to be carried out carefully and the advantages of this pre-treatment can be appreciated especially for very low concentration measurements. The need for the conditioning mainly results from the necessity of a complete permeation of all the different tortuous channels constituting the membrane itself.

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Could N-(diethylcarbamothioyl)benzamide be a good ionophore for sensor membranes?

Cited by 21 publications

References 35 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

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

Polymeric membranes conditioning for sensors applications: mechanism and influence on analytes detection

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