Synthesis, spectroscopic, DNA binding and DFT analysis of new charge transfer complexes of 2-Ethyl-6-methylaniline with DDQ and p-Chloranil

Manojkumar, P.; Gorle, Suresh; Mahipal, Varukolu; Macha, Ramesh; Tigulla, Parthasarathy

doi:10.1016/j.cdc.2020.100493

Cited by 15 publications

(8 citation statements)

References 46 publications

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“…The presence of the essential IR bands of the donor and acceptor in the spectrum of the CT complex strongly favors the CT complexation. 32 However, the bands of the 4-DMAP and DDQ in this complex reveal small shifts in both band intensities and wave number values from those of the free reactants. The characteristic absorption bands were identified in the infrared spectra of free DDQ at 1651, 2232, 1515, 1165, and 757 cm –1 assigned to υ (C=O), (C≡N), (C=C), (C–C), and (C–Cl) respectively.…”

Section: Results and Discussionmentioning

confidence: 81%

“…The important band assignments are depicted in Table . The presence of the essential IR bands of the donor and acceptor in the spectrum of the CT complex strongly favors the CT complexation . However, the bands of the 4-DMAP and DDQ in this complex reveal small shifts in both band intensities and wave number values from those of the free reactants.…”

Section: Results and Discussionmentioning

confidence: 90%

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New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies

et al. 2021

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A combined experimental and theoretical study of the electron donor 4-dimethylaminopyridine (4-DMAP) with the electron acceptor 2, 3-dichloro-5, 6-dicyano- p -benzoquinone (DDQ) has been made in acetonitrile (ACN) and methanol (MeOH) media at room temperature. The stoichiometry proportion of the charge transfer (CT) complex was determined using Job’s and photometric titration methods and found to be 1:1. The association constant ( K CT ), molar absorptivity (ε), and spectroscopic physical parameters were used to know the stability of the CT complex. The CT complex shows maximum stability in a high-polar solvent (ACN) compared to a less-polar solvent (MeOH). The prepared complex was characterized by Fourier transform infrared, NMR, powder X-ray diffraction, and scanning electron microscopy–energy-dispersive X-ray analysis. The nature of DNA binding ability of the complex was probed using UV–visible spectroscopy, and the binding mode of the CT complex is intercalative. The intrinsic binding constant ( K b ) value is 1.8 × 10 6 M –1 . It reveals a primary indication for developing a pharmaceutical drug in the future due to its high binding affinity with the CT complex. The theoretical study was carried out by density functional theory (DFT), and the basis set is wB97XD/6-31G(d,p), with gas-phase and PCM analysis, which supports experimental results. Natural atomic charges, state dipole moments, electron density difference maps, reactivity parameters, and FMO surfaces were also evaluated. The MEP maps indicate the electrophilic nature of DDQ and the nucleophilic nature of 4-DMAP. The electronic spectrum computed using time-dependent DFT (TD-DFT) via a polarizable continuum salvation approach, PCM/TD-DFT, along with natural transition orbital analysis is fully correlated with the experimental outcomes.

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Section: Results and Discussionmentioning

confidence: 81%

Section: Results and Discussionmentioning

confidence: 90%

New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies

et al. 2021

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“…The Mullikan color range of 2 MQ, CHLA, and the HB CT complex in the gas phase and PCM analysis 60 are depicted in Fig. S9 and S10.…”

Section: Resultsmentioning

confidence: 99%

“…Aer adding the DNA solution to the complex, the binding interaction of the HB CT complex through DNA helices is dened by changes in absorbance and wavelength. 59,60 The binding affinity was evaluated in this current study by observing the absorbance change of the CT complex when the CT-DNA concentration increased as well as when the CT complex concentration was kept constant. The absorption spectra of the CT-DNA binding with HB CT complex are presented in Fig.…”

Section: Dna Binding Studiesmentioning

confidence: 99%

Exploring the charge transfer dynamics of hydrogen bonded crystals of 2-methyl-8-quinolinol and chloranilic acid: synthesis, spectrophotometric, single-crystal, DFT/PCM analysis, antimicrobial, and DNA binding studies

et al. 2021

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“…The energy of the CTC ( E CTC ) value obtained 43 , 44 by the following relation: where denotes the wavelength (nm) at CT-absorption band observed from the abs versus wavelength plot. The E CTC supports the strength of the donor–acceptor complex.The values of E CTC are shown in Table 1 .…”

Section: Evaluation Of the Spectroscopic Physical Parametersmentioning

confidence: 99%

Charge Transfer Complex betweenO-Phenylenediamine and 2, 3-Dichloro-5, 6-Dicyano-1, 4-Benzoquinone: Synthesis, Spectrophotometric, Characterization, Computational Analysis, and its Biological Applications

et al. 2022

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UV–vis electronic absorption spectroscopy was used to investigate the new molecular charge transfer complex (CTC) interaction between electron donor O -phenylenediamine (OPD) and electron acceptor 2,3-dichloro-5,6-dicyano- p -benzoquinone (DDQ). The CTC solution state analysis was carried out by two different polarities. The stoichiometry of the prepared CTC was determined by using Job’s, photometric, and conductometric titration methods and was detemined to be 1:1 in both solvents (at 298 K). The formation constant and molar extinction coefficient were determined by applying the modified (1:1) Benesi–Hildebrand equation. The thermodynamic parameter Δ G ° result indicated that the charge transfer reaction was spontaneous.The stability of the synthesized CTC was evaluated by using different spectroscopic parameters like the energy, ionization potential, oscillator strength, resonance energy, dissociation energy, and transition dipole moment. The synthesized solid CTC was characterized by using different analytical methods, including elemental analysis, Fourier transform infrared, nuclear magnetic resonance, TGA-DTA, and powder X-ray diffraction. The biological evolution of the charge transfer (CT) complex was studied by using DNA binding and antibacterial analysis. The CT complex binding with calf thymus DNA through an intercalative mode was observed from UV–vis spectral study. The CT complex produced a good binding constant value (6.0 × 10 5 L.mol –1 ). The antibacterial activity of the CT complex shows notable activity compared to the standard drug, tetracycline. These results reveal that the CT complex may in future be used as a bioactive drug. The hypothetical DFT estimations of the CT complex supported the experimental studies.

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Synthesis, spectroscopic, DNA binding and DFT analysis of new charge transfer complexes of 2-Ethyl-6-methylaniline with DDQ and p-Chloranil

Cited by 15 publications

References 46 publications

New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies

New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies

Exploring the charge transfer dynamics of hydrogen bonded crystals of 2-methyl-8-quinolinol and chloranilic acid: synthesis, spectrophotometric, single-crystal, DFT/PCM analysis, antimicrobial, and DNA binding studies

Charge Transfer Complex betweenO-Phenylenediamine and 2, 3-Dichloro-5, 6-Dicyano-1, 4-Benzoquinone: Synthesis, Spectrophotometric, Characterization, Computational Analysis, and its Biological Applications

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