Density functional study of molecular recognition and reactivity of thiourea derivatives used in sensors for heavy metal polluting cations

Pérez-Marín, L.; Castro, Miguel; Otazo-Sánchez, Elena María; Cisneros, G. Andrés

doi:10.1002/1097-461x(2000)80:4/5<609::aid-qua10>3.0.co;2-3

Cited by 15 publications

(14 citation statements)

References 23 publications

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“…Thiourea derivatives has attracted interest due to their potential use as reagents for the separation of metal ions [7][8][9] and in biological applications for example; antibacterial [3,8,10,11], antiviral [7] antifungal agents [7,8,[12][13][14]. And thioureas have recently taken attention as protease inhibitors of human immunodeficiency virus (HIV) [3,15,16].…”

Section: Introductionsupporting

confidence: 79%

Classical and Microwave-Assisted Synthesis of Substituted-Dihydroxy-imidazolidine-2-thiones Compounds

Pıhtılı¹,

Tuncer²

2017

HJBC

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B u çalışmada, aromatik aminlerin, fenilizotiyosiyanat ve 4-metoksi-fenilizotiyosiyanat ile tepkimesi ile, N-sübstütiye-N'-feniltiyoüre ve türevleri sentezlendi. Daha sonra sentezlenen bu bileşikler, asidik ortamda sulu glioksal çözeltisi ile reflaks edildi ve N,N'-disübstütiye-4,5dihidroksi-imidazolidin-2-tiyon bileşikleri sentezlendi. N-sübstütiye-N'-feniltiyoürenin sentezi, geleneksel ısıtma yöntemi kullanılarak gerçekleştirildi. Tiyoüre türevlerinin sentezi hem klasik yöntem hem de mikrodalga destekli sentez yöntemiyle yapıldı. Mikrodalga destekli tepkimeler, sıcaklık ve basınç kontrollü cihazla atmosfer basınçlı ortamda gerçekleştirildi. Tüm ürünler, FT-IR ve 1 H-NMR spektroskopik analiz yöntemleri ile karakterize edildi. Anahtar kelimelerHalkalı tiyoüre, aromatik amin, mikrodalga destekli sentez, imidazolidin-2-tiyon.

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Section: Introductionsupporting

confidence: 79%

Classical and Microwave-Assisted Synthesis of Substituted-Dihydroxy-imidazolidine-2-thiones Compounds

Pıhtılı¹,

Tuncer²

2017

HJBC

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“…Since 1930s, potentiometric membrane sensors have been found to possess wide applications in various fields (Faridbod et al 2008). They had been used frequently in the monitoring of environmental pollution, quality control in the industrial process, clinical analysis and biochemical analysis due to their advantages of simple construction, relatively fast response, wide linear range, reasonable selectivity and can be utilized for direct measurement of a wide variety of ions in complex samples (Ghaneimotlagh et al 2014;Kopylovich et al 2011;Perez-Marín et al 2000;Siswanta et al 2016). This type of membrane sensor has been designed based on molecular recognition, consist an incorporated carrier or ionophore within the membrane that could strongly recognize the target ion in the presence of other interference ions (Kopylovich et al 2011).…”

Section: Introductionmentioning

confidence: 99%

A New Copper Ionophore N1, N3-Bis [[3,5-Bis(Trifluoromethyl)Phenyl] Carbamothioyl] Isophtalamide for Potentiometric Sensor

Kook

Lee²,

Hassan³

et al. 2018

JSM

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A copper ion sensor based on a new bis-thiourea compound N 1 ,N 3-bis[[3,5-bis(trifluoromethyl)phenyl]carbamothioyl] isophthalamide (or TPC) as neutral carrier was investigated. The immobilization of the TPC into poly(n-butyl acrylate) (pBA) membrane via drop casting and the sensor was characterized by potentiometry. The sensor fabricated from TPC only showed a good Nernstian response towards copper ion with a sensitivity slope of 28.81±0.53mV/decade in the range of 1.0 × 10-6-1.0 × 10-4 M. The limit of detection of this sensor was found to be 6.11 × 10-7 M and with short sensor response time (60-80 s). This sensor also demonstrated reversibility and reproducibility with 3.69% and 1.84% (Relative Standard Deviation, RSD), respectively. Based on the separate solution method (SSM), the logarithm selectivity coefficients were better than-2.00 for monovalent, divalent and trivalent cations and this confirmed that the sensor exhibited good selectivity towards copper ion. The sensor could attain optimum function without the need in the inclusion of either lipophilic anions as a membrane additive nor plasticizer as a membrane softener. Thus, these are the main advantages. The addition of lipophilic anions into the pBA membrane could cause the sensitivity and selectivity of the copper ion sensor based on ionophore TPC to deteriorate.

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“…20 The calculated structural parameters do not agree with those reported here by XRD, with the exception of the observed "U"-shaped arrangement of the CO and CS groups. The main differences are observed with the dihedral angles.…”

Section: Xrd Structuresmentioning

confidence: 99%

“…The theoretical structures calculated for 2f 21 and 2a 20 agree with this fact, therefore, the reported orbital data are reliable. Consideration of the frontier orbitals suggests that coordination with soft heavy-metal ions should only be through the sulfur atom with no chelate formation taking place.…”

Section: Xrd Structuresmentioning

confidence: 99%

Aroylthioureas: new organic ionophores for heavy-metal ion selective electrodes

Otazo-Sánchez

Pérez-Marín

Estévez-Hernández

et al. 2001

J. Chem. Soc., Perkin Trans. 2

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Thiourea derivatives (46 aroylthioureas) having different substituents close to the sulfur atom were synthesized and their ionophore potential in ion selective electrodes (ISEs) was examined. Structural considerations were taken into account based on the corresponding heavy-metal ISE parameters. As ionophores, some 1-furoyl-3-substituted thioureas (series 2) gave the best results in Pb(), Hg() and Cd() ISEs. The strong intramolecular hydrogen bond in series 2 allows ligand interaction only through the C᎐ ᎐ S group. Substituents on the furan and phenyl rings give rise to low solubility in the membrane plasticizer. 3-Alkyl substituted furoylthioureas improve solubility but enhance oxidative processes with chain length. New X-ray diffraction (XRD) structures and theoretical DFT calculations were considered in the analysis of the substituent influence on the selectivity of ISEs. These new ionophores have advantages because of their stability, simple synthesis and easy modification of the sulfur binding ability resulting from substitution.

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Density functional study of molecular recognition and reactivity of thiourea derivatives used in sensors for heavy metal polluting cations

Cited by 15 publications

References 23 publications

Classical and Microwave-Assisted Synthesis of Substituted-Dihydroxy-imidazolidine-2-thiones Compounds

Classical and Microwave-Assisted Synthesis of Substituted-Dihydroxy-imidazolidine-2-thiones Compounds

A New Copper Ionophore N1, N3-Bis [[3,5-Bis(Trifluoromethyl)Phenyl] Carbamothioyl] Isophtalamide for Potentiometric Sensor

Aroylthioureas: new organic ionophores for heavy-metal ion selective electrodes

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