Spectrophotometric and theoretical studies of the protonation of Allura Red AC and Ponceau 4R

Bevziuk, Kateryna; Чеботарев, А. Н.; Снігур, Д. В.; Bazeľ, Yaroslav; Fizer, Maksym; Sidey, Vasyl

doi:10.1016/j.molstruc.2017.05.001

Cited by 55 publications

(20 citation statements)

References 22 publications

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“…The reciprocal position of substituents in thiourea is usually opposite . Finding of the most stable conformer can play a crucial role in the investigation of reactivity . This is why, in order to find the most stable conformer in chloroform solution, we have studied four possible conformers of N ‐allyl‐ N ′‐phenylthiourea ( 4 ) (Fig.…”

Section: Resultsmentioning

confidence: 99%

Reactions of N‐alkenyl Thioureas with p‐alkoxyphenyltellurium Trichlorides

Kut

Fizer

Onysko

et al. 2018

Journal of Heterocyclic Chem

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N‐Аlkenyl thioureas, under the action of aryltellurium trichlorides, form the addition products N‐{2‐chloro‐3‐[dichloro(4‐alkoxyphenyl)‐tellanyl]propyl} thioureas or the intramolecular cyclization products 5‐{dichloro(4‐alkoxyphenyl)‐telluromethyl}‐2‐phenylamino‐4,5‐dihydro‐1,3‐thiazole hydrochlorides. The reaction route depends on the nature of the substituent in the thiourea. The Fukui function reactivity indexes identify the electrophilic/nucleophilic centers and explain the possible cyclization reaction in the case of phenyl substituted thioureas. In the case of other substituents, the calculated values of partial atomic charges clearly predict that the addition reaction is more possible.

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Section: Resultsmentioning

confidence: 99%

Reactions of N‐alkenyl Thioureas with p‐alkoxyphenyltellurium Trichlorides

Kut

Fizer

Onysko

et al. 2018

Journal of Heterocyclic Chem

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“…On the contrary, under alkaline conditions, the structure of AR is R 3− with dihedral ( Figure 2) due to the electrostatic repulsion of negative charge fragments of methoxy and naphthol anions. The formation of this structure is also related to the slight rotation of the benzene ring [36]. This molecular structure was not conducive to enhancing the RRS signal.…”

Section: Effects Of Aciditymentioning

confidence: 95%

“…They would form intramolecular hydrogen bonds, thus increasing the planarity of AR. The Kateryna Bbvziuk research [36] also showed that when pH was less than 4.00, the molecular structures of AR after protonation at different pH values were different, but they were all rigid planar structures ( Figure 2). So, when the system was under acidic conditions, the RRS value had a platform.…”

Section: Effects Of Aciditymentioning

confidence: 96%

Application of Gelatin Decorated with Allura Red as Resonance Rayleigh Scattering Sensor to Detect Chito-Oligosaccharides

Zou

Sun

et al. 2020

Marine Drugs

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A convenient and sensitive triple-wavelength overlapping resonance Rayleigh scattering (TWO-RRS) method for the detection of chito-oligosaccharides (COS) was proposed based on enhancing the rigid surface of porous reticular spatial structure of gelatin and COS by introducing allura red AC (AR). The interaction and resultant porous reticular spatial structure were characterized with transmission electron microscopy (TEM), RRS, and UV-Vis spectroscopy. The results indicated that gelatin and COS formed porous reticular spatial structure with an average diameter of 1.5–2.0 μm, and the RRS value of COS-AR-gelatin ternary system with gelatin participation was significantly higher than that of COS-AR binary system. Under the optimal conditions, the enhanced TWO-RRS intensity of the system was linearly proportional to COS concentration in the range of 0.30–2.50 μg/mL, and the regression equation was ΔI = 4933.2c − 446.21 with R2 = 0.9980. The limit of detection was 0.0478 μg/mL. So, a new method for the detection of COS was established and verified in the health products with satisfactory results.

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“…Also, in our previous studies, it has been found that PM7 can model similar organic compounds containing C, H, N, O, S very well. [10][11][12] Next step was the geometry optimization in water continuum COSMO solvation model 13 with the DFT B97-D3/6-31+G(d,p) method 14 that includes the Grimme's DFT-D3 dispersion correction. 15,16 Single-point energies were computed with evaluation of larger 6-311++G(d,p) basis set that contains diffuse functions for all atoms.…”

Section: Experimental and Computationalmentioning

confidence: 99%

“…Semi-empirical and DFT studies on similar dyes containing C, H, N, O, S have previously been reported in the literature. 10,30,31 PBV contains two sulfo groups (strongly acidic), one OH phenolic group (weakly acidic) and two diethylamino groups, which also could act as an acid when protonated. Due to the presence of non-identical reactivity centers in the dye, it is important to consider the protonation/deprotonation of each acidic group and nitrogen atoms in order to determine the preferred protonation site.…”

Section: Acid-base Equilibria Of Patented Blue V In Aqueous Solutionsmentioning

confidence: 99%

Protonation of Patented Blue V in aqueous solutions: theoretical and experimental studies

et al. 2018

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The acid-base properties of the Patented Blue V dye were studied by spectrophotometry and tristimulus colourimetry. The mechanism of protonation of Patented Blue V has been investigated with semiempirical and DFT methods. The quantum chemical calculations of total energy defined the most stable isomer for each protonated form in water solution. In addition to thermodynamic parameters, the condensed Fukui function and molecular electrostatic potential were successfully used as reactivity descriptors for the determination of the most favorable site for protonation. Moreover, for the explanation of the structure of the most deprotonated form of the dye in highly basic medium, the weak intramolecular interactions were investigated with the reduced density gradient function. The semi-empirical calculations of absorbance spectra explained the changing of the colour of the dye for the different protonated states. It has been shown that the dominant form of the Patented Blue V was the electro-neutral form, and the molar absorptivity (ε 639 = 1.06×10 5 dm 3 •mol −1 •cm −1) increases with the increase of the dielectric permittivity of the solvent. The replacement of polar solvents by less polar ones is causing a bathochromic shift of the absorption band of the dye, the value of which is correlated with the value of the Hansen parameter.

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Spectrophotometric and theoretical studies of the protonation of Allura Red AC and Ponceau 4R

Cited by 55 publications

References 22 publications

Reactions of N‐alkenyl Thioureas with p‐alkoxyphenyltellurium Trichlorides

Reactions of N‐alkenyl Thioureas with p‐alkoxyphenyltellurium Trichlorides

Application of Gelatin Decorated with Allura Red as Resonance Rayleigh Scattering Sensor to Detect Chito-Oligosaccharides

Protonation of Patented Blue V in aqueous solutions: theoretical and experimental studies

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