Sparfloxacin charge transfer complexes with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and tetracyanoquinodimethane: Molecular structures, spectral, and DFT studies

Shehab, Ola R.; Mansour, Ahmed M.

doi:10.1016/j.molstruc.2015.03.048

Cited by 23 publications

(6 citation statements)

References 35 publications

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“…When investigating the reactive sites for electrophilic attacks, nucleophilic reactions, or H-bonding interactions, the molecular electrostatic potential map is vital. 38 Specific electrostatic potential values are marked with different colors. The color map used is follows: red ˂ orange ˂ yellow ˂ green ˂ blue.…”

Section: Molecular Electrostatic Potentialmentioning

confidence: 99%

<p>Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study</p>

Yousef¹,

Ezzeldin²,

Abdel‐Aziz³

et al. 2020

DDDT

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Background: Electron donor-acceptor interactions are important molecular reactions for the activity of pharmacological compounds. The aim of the study is to develop a charge transfer (CT) complex: synthesis, characterization, antimicrobial activity, and theoretical study. Method and Results: A solid CT complex of neostigmine (NSG) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was synthesized and characterized by infrared spectra, NMR, and UV-visible spectroscopy. The results confirm the formation of a CT complex. The stability of the CT complex between NSG and DDQ in acetonitrile was determined in solution via spectrophotometric measurement, ie, by calculating the formation constant, molar extinction coefficient, and different spectroscopic parameters. The stoichiometry of the formed NSG-DDQ complex was determined using Job's method. The absorption band of the NSG-DDQ complex can be used for the quantification of NSG. Conclusion: The DFT geometry optimization of NSG, DDQ, and the CT complex and the UV comparative study of both theoretical and experimental structures are presented. The experimental results confirm the charge transfer structure. The bacterial study shows that the NSG-DDQ complex has good antibacterial activity against both Gram-positive and Gramnegative bacteria as well as antifungal activity against Candida albicans.

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Section: Molecular Electrostatic Potentialmentioning

confidence: 99%

<p>Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study</p>

Yousef¹,

Ezzeldin²,

Abdel‐Aziz³

et al. 2020

DDDT

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“…These peaks might be attributed to p-p* transitions (medium and low) in the aromatic moiety, piperazine ring and C]O transitions, respectively. [29][30][31] The formation of two new bands at 390 and 464 nm can be explained based on the formation of a donor-acceptor (D-A) complex, since neither SFX nor TCNE alone absorb in this region. It is imperative to mention that the ndings reported herein show that these two peaks, representing two CTSs, increase and decrease simultaneously depending on the experimental conditions, unlike our previously reported CT of synephrine, where two types of complexes were formed.…”

Section: Charge-transfer (Ct) Reactionmentioning

confidence: 99%

Application of a definitive screening design for the synthesis of a charge-transfer complex of sparfloxacin with tetracyanoethylene: spectroscopic, thermodynamic, kinetics, and DFT computational studies

et al. 2019

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“…The MEP is the most convenient electrostatic property to study the relation between structure and activity of a molecule that describes the interaction energy between the electrical charges generated from electron and nuclei of the molecule . The MEP maps are used to visualize variably charged regions of a molecule and is a good guide to assess the reactivity of the molecule towards positively or negatively charged reactants.…”

Section: Computational Studiesmentioning

confidence: 99%

Synthesis, spectroscopic, and computational studies of charge-transfer complexation between benzidine with 2,3-dichloro-5,6-dicyano-p-benzoquinone and chloronil

et al. 2017

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The solid charge transfer (CT) complexes that have been formed from the reactions of donor benzidine (BZ) and the π-acceptors such as 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) and chloronil (CHL) have been studied and characterized experimentally and theoretically. The experimental work which includes the use of UV-visible spectroscopy to identify the CT band of the CT-complex. The composition of the complexes has been investigated successfully by using spectrophotometric titration and Job method of continuous variation to be 1:1. Furthermore, to calculate the formation constant and molar extinction coefficient, we have used the Benesi-Hildebrand equation. Infrared and proton nuclear magnetic resonance spectral studies were used to characterize and confirm the formation of CT-complex. The experimental studies were well supported by quantum chemical simulations by using density functional theory. The computational analysis of molecular geometry, Mulliken charges, and molecular electrostatic potential surfaces of reactants and complexes is very much helpful in assigning the CT route. The C═O bond length of DDQ and CHL increased upon complexation with BZ. We have also observed that the substantial amount of charge has been transferred from BZ to DDQ and CHL in the process of complexation. An excellent consistency has been achieved between experimental and theoretical results.

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Sparfloxacin charge transfer complexes with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and tetracyanoquinodimethane: Molecular structures, spectral, and DFT studies

Cited by 23 publications

References 35 publications

<p>Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study</p>

<p>Charge Transfer Complex of Neostigmine with 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone: Synthesis, Spectroscopic Characterization, Antimicrobial Activity, and Theoretical Study</p>

Application of a definitive screening design for the synthesis of a charge-transfer complex of sparfloxacin with tetracyanoethylene: spectroscopic, thermodynamic, kinetics, and DFT computational studies

Synthesis, spectroscopic, and computational studies of charge-transfer complexation between benzidine with 2,3-dichloro-5,6-dicyano-p-benzoquinone and chloronil

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