Quantum-Mechanical and Solvatochromic Characterization of Quercetin

Morosanu, Ana Cezarina; Benchea, Andreea Celia; Babusca, Daniela; Dimitriu, Dan Gheorghe; Dorohoi, Dana Ortansa

doi:10.1080/00032719.2017.1291657

Cited by 18 publications

(10 citation statements)

References 36 publications

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“…However, the hydrogen bond basicity of a solvent has a considerable negative effect on the electronic transition energy of quercetin. 20 It means that, as observed in Fig. 2, bathochromic shifts occurs and E T decreases as the hydrogen bond basicity of mixture increases by raising the mole fraction of DMSO, DMF and DMAC.…”

Section: Solvatochromism Of Quercetinmentioning

confidence: 55%

“…The dipole moment of quercetin increases in its excited state, with respect to the ground state. 20 In this view, it is expected that the decrease in polarity of a solvent when an aprotic solvent mole fraction increases in a binary mixture leads to a hypsochromic shift. However, the hydrogen bond basicity of a solvent has a considerable negative effect on the electronic transition energy of quercetin.…”

Section: Solvatochromism Of Quercetinmentioning

confidence: 99%

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Preferential solvation of quercetin in aqueous aprotic solvent mixtures

Faraji

Farajtabar

2020

JSCS

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Solvatochromism of quercetin was studied in binary mixtures of water with dimethyl sulfoxide, N,N-dimethylformamide and N,N-dimethylacetamide at 25 °C by UV-Vis measurements. For all mixtures, a non-linear trend was observed in spectral shifts plotted against the bulk mole fractions. Deviation from ideal behaviour indicates that the solvation shell of quercetin differs in composition from the bulk because of preferential solvation. The solvent exchange model was applied in the analysis of solvatochromic data in order to quantify the extent of preferential solvation in the case of solute-solvent and solvent-solvent intermolecular interactions. The results show that the solvation shell of quercetin is enriched in aprotic solvent and the complex that was formed by the interaction between water and an aprotic solvent, over the whole composition range. The distribution of the solvent species in the solvation cage was obtained from the calculation of the local mole fractions as a function the bulk composition. It shows that the solvent-solvent interactions have great influence on the solvation behaviour of quercetin in aqueous aprotic solvent mixtures.

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Section: Solvatochromism Of Quercetinmentioning

confidence: 55%

Section: Solvatochromism Of Quercetinmentioning

confidence: 99%

Preferential solvation of quercetin in aqueous aprotic solvent mixtures

Faraji

Farajtabar

2020

JSCS

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“…The polar surface area (PSA) [ 47 , 48 , 49 , 50 , 51 ] defined as the sum of the polar atoms’ surfaces in a molecule is a useful parameter for prediction of drug transport properties. The values of PSA are between 28.490 and 29.781 Å 2 , these molecules being able to cross both the cell membranes and the blood-brain barrier.…”

Section: Resultsmentioning

confidence: 99%

Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity

et al. 2021

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New di-(β-chloroethyl)-amides of some acids derived from 2-mercaptobenzoxazole were prepared by reaction of the corresponding pivalic mixed anhydrides with di-(β-chloroethyl)-amine. A study regarding the optimization of the chemical reactions was made for the case of di-(β-chloroethyl)-amines. The quantum chemical analysis by Spartan’14 was made in order to establish the most stable configuration of the ground electronic states for the obtained chemical structures and some physico-chemical parameters of N-mustards reported in this paper. Mercaptobenzoxazoles substituted in the side chain with the cytotoxic group show antitumor activity and they inhibit Ehrlich Ascites in an appreciable proportion compared to the drug I.O.B.-82, as our studies evidenced.

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“…The data show that the dispersionpolarization interactions have the greatest contribution to If only the electronic absorption spectra of a molecule in different solvents are available, a variational method could be applied to obtain information on both the electric dipole moment in the excited state of the studied molecule and the angle between the dipole moments in the electronic states participating in absorption process. Such a procedure, described below, was successfully applied for other molecules [52][53][54][55][56].…”

Section: Resultsmentioning

confidence: 99%

Variational Method for Estimating the Dipole Moment in the Second Excited State of Fluorescein Molecule from its Electronic UV Absorption Spectra

Luca¹,

Morosanu²,

Macovei³

et al. 2019

Rev. Chim.

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Electro-optical parameters of fluorescein molecule in the second excited electronic state and information on the interactions with solvents were obtained from a solvatochromic study. Parameters of the solvents such as the refractive index, electrical permittivity and Kamlet-Taft parameters (hydrogen bond acidity and basicity) were related with the experimentally recorded shifts of UV absorption spectral band of fluorescein dissolved in several solvents. Through a variational method, the electric dipole moment and polarizability in excited state of fluorescein molecule were estimated. The calculus requires some parameters of the fluorescein molecule in the ground electronic state, which were determined through a quantum-mechanical study.

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Quantum-Mechanical and Solvatochromic Characterization of Quercetin

Cited by 18 publications

References 36 publications

Preferential solvation of quercetin in aqueous aprotic solvent mixtures

Preferential solvation of quercetin in aqueous aprotic solvent mixtures

Optimized Synthesis of New N-Mustards Based on 2-Mercaptobenzoxazole Derivatives with Antitumor Activity

Variational Method for Estimating the Dipole Moment in the Second Excited State of Fluorescein Molecule from its Electronic UV Absorption Spectra

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