Donor-acceptor complex of 1-benzoylpiperazine with p-chloranil: Synthesis, spectroscopic, thermodynamic and computational DFT gas phase/PCM analysis

Baindla, Naveen; Abbu, Venugopal; Gorle, Suresh; Mahipal, Varukolu; Manojkumar, P.; Tigulla, Parthasarathy

doi:10.1016/j.molstruc.2019.06.083

Cited by 43 publications

(22 citation statements)

References 37 publications

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“…After adding the DNA solution to the complex, the binding interaction of the formed complex through DNA helices is defined by changes in absorbance and wavelength. 35 The binding affinity was evaluated in this current study by observing the absorbance alteration of the CT complex when the CT-DNA concentration rises and when the CT complex concentration was kept constant. The absorption spectrum of the CT-DNA binding with the CT complex is presented in Figure 7 .…”

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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“…Compared with 1 and 2 , we drew a conclusion that energies of complex 1 were reversely low and its gap was smaller; the E LUMO and E HOMO energies levels are all negative for both complexes, certifying the complexes are relatively stable. [ 59 ] Furthermore, the plot of the highest occupied molecular orbitals (HOMOs) were delocalized and stayed primary on the orbitals of metal ion. [ 60 ] Comparatively, the LUMOs were less localized and distribute in the orbitals of the whole Schiff base fragment and M (II).…”

Section: Resultsmentioning

confidence: 99%

Co (II) and Cd (II) complexes with imidazole‐2‐carboxaldehyde groups: spectroscopic, antibacterial, Hirshfeld surfaces analyses, and TD/DFT calculations

Chai

et al. 2021

Applied Organom Chemis

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Two complexes [Co(L) 2 Á2CH 3 OH] 2 Á(NO 3 ) 4 (1) and [Cd(L) 2 (NO 3 ) 2 ] (2) (L = 2-(2-imidazolyl)-4-methyl-1,2-dihydroquinazoline-3-oxide) were synthesized by natural evaporation of Co (II)/Cd (II) nitrate with a new heterocyclic ligand. The metal complexes are characterized by elemental analysis, spectroscopy, and X-ray crystallographic. In the crystal structures, Co (II) complex 1 was in a six-coordinated coordination environment and constituted an infinite 1-D chain, 2-D network, Meter-shaped 3-D supramolecular framework, while Cd (II) complex 2 assembled into an infinite 1-D, wave-like 2-D, and dragonfly-shaped 3-D skeleton. Specifically, nitrate ions were present as a dissociated group in complex 1, whereas complex 2 was involved in the coordination. Moreover, Cd (II) complex exhibited different fluorescence behaviors in diverse solvents. Remarkably, all the compounds have shown perceptible antibacterial activity against Gram-positive and Gram-negative bacteria. Furthermore, the electrostatic potential (ESP) calculations were utilized to analyze electrophilic and nucleophilic attack sites on the molecule, which verified the existence of hydrogen bonds in the optimized crystal structure. In addition, the structural features of metal complexes have been remarkably rationalized, and the overall trends obtained in the experimental values have been resoundingly remade by TD/DFT calculations. The detailed Hirshfeld surface analysis and fingerprint plots yielded a comparative picture of the mode of non-covalent interactions.

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“…Among the solvents, acetonitrile is aprotic while methanol and ethanol are protic, and these protic solvents support the intermolecular hydrogen bonding between the OH group of methanol and ethanol with 2 MQ, to attain the stability of the HB CT complex. The mixing of the donor (0.0005 M) and acceptor (0.0005 M) produces an instant violet color 35,36 (Scheme 1), which seems to produce the proton transfer hydrogen bonded CT complex in all three solvents, and the probable mechanism is shown in Scheme 2. Moreover, the absorbance of the HB CT complex increases with increasing donor concentration without changing the l max of the complex, suggesting the formation of a stable HB CT complex.…”

Section: Resultsmentioning

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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Donor-acceptor complex of 1-benzoylpiperazine with p-chloranil: Synthesis, spectroscopic, thermodynamic and computational DFT gas phase/PCM analysis

Cited by 43 publications

References 37 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

Co (II) and Cd (II) complexes with imidazole‐2‐carboxaldehyde groups: spectroscopic, antibacterial, Hirshfeld surfaces analyses, and TD/DFT calculations

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

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