Spectroscopic analysis, thermodynamic study and molecular modeling of charge transfer complexation between 2-amino-5,6-dimethyl-1,2,4-triazine with DDQ in acetonitrile

Al-Attas, Amirah S.; Al-Raimi, Doaa S.; Habeeb, Moustafa M.

doi:10.1016/j.molliq.2014.06.015

Cited by 23 publications

(9 citation statements)

References 29 publications

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“…In the time study of the CT complex in can, the bands at 617 and 436 nm remain constant with time, but a band at 469 nm disappeared with time, as shown in Figure S1. These multicharge transfer transitions take place from more than one closely located higher occupied molecular orbital of the donor to the higher unoccupied molecular orbital(s) of the acceptor . The instantaneous production of constant reddish-brown color is mainly recognized as the formation of a radical anion of DDQ resulting in the electron transfer from 4-DMAP to DDQ (Scheme ).…”

Section: Results and Discussionmentioning

confidence: 99%

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: 99%

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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“…Basic molecular modelling computations such as alignment, stochastic conformational sampling, dihedral driver and MM2 experiments can be effectively facilitated by using this software. Moreover, it can be used in prediction and visualization NMR, IR ,Raman and UV spectra [23][24][25][26][27][28].…”

Section: A N U S C R I P Tmentioning

confidence: 99%

Spectroscopic investigation and computational analysis of charge transfer hydrogen bonded reaction between 3-aminoquinoline with chloranilic acid in 1:1 stoichiometric ratio

Al-Ahmary

Alenezi

Habeeb

2015

Journal of Molecular Structure

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“…On the other hand a simultaneous reddish brown color has been clearly observed upon mixing donor and acceptor solution which is considered a hallmark of charge transfer complex formation. The instantaneous production of stable reddish brown color is presumably attributed to the formation of radical anion of DDQ resulting from the electron transfer from DMP towards DDQ [23][24][25].…”

Section: Spectral Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Spectroscopic studies and molecular orbital calculations of charge transfer complexation between 3,5-dimethylpyrazole with DDQ in acetonitrile

Habeeb

Al-Attas

Al-Raimi

2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Spectroscopic analysis, thermodynamic study and molecular modeling of charge transfer complexation between 2-amino-5,6-dimethyl-1,2,4-triazine with DDQ in acetonitrile

Cited by 23 publications

References 29 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

Spectroscopic investigation and computational analysis of charge transfer hydrogen bonded reaction between 3-aminoquinoline with chloranilic acid in 1:1 stoichiometric ratio

Spectroscopic studies and molecular orbital calculations of charge transfer complexation between 3,5-dimethylpyrazole with DDQ in acetonitrile

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