DFT/ and TD-DFT/PCM calculations of molecular structure, spectroscopic characterization, NLO and NBO analyses of 4-(4-chlorophenyl) and 4-[4-(dimethylamino) phenyl]-2-oxo-1,2,5,6-tetrahydrobenzo[ h ]quinoline-3-carbonitrile dyes

Wazzan, Nuha; Al−Qurashi, Ohoud S.; Faidallah, Hassan M.

doi:10.1016/j.molliq.2016.07.146

Cited by 43 publications

(14 citation statements)

References 59 publications

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“…The angle between μ g and μ e was 0 0 for both the 3HOCE and 3MOCE compounds, which confirmed that the dipole moments were collinear. All values were in agreement with values reported in the literature …”

Section: Resultssupporting

confidence: 92%

“…Here, μ e was found to be greater than μ g , this indicated the less polar nature of the solutes in the ground state than in the excited state. The increase in dipole moment after excitation helps in the understanding the twisted intramolecular charge transfer (TICT) characteristics of the excited species . The angle between μ g and μ e was 0 0 for both the 3HOCE and 3MOCE compounds, which confirmed that the dipole moments were collinear.…”

Section: Resultsmentioning

confidence: 74%

“…The nucleophilic and electrophilic nature of the compounds was identified using the coloured regions. Electrostatic potential V(r) of the compounds could be determined using equation as given below:

V ((), r) = \sum ([], \frac{Z_{R}}{R_{A} - r}) - \int ([], \frac{ρ (r^{'})}{r^{'} - r})

where Z R charge of nucleus A located at R A ρ ( r ′) electron density function of the solute r ′ integration variable of dummy. …”

Section: Resultsmentioning

confidence: 99%

“…Quantum mechanical Onsager's reaction field theories and second order perturbation theory have been correlated . Coumarin compounds have high potential application and extensive significance in structural discovery . Density functional theory (DFT) provides valuable information on molecular reactivity and charge density‐based local reactivity descriptors, which play a significant role in the design of new pharmaceutical compounds .…”

Section: Introductionmentioning

confidence: 99%

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Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

2020

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An attempt was made to determine the ground state and excited state dipole moments and quantum chemical computations of two coumarin compounds, namely 3‐hydroxy‐3‐[2‐oxo‐2‐(2‐oxo‐2H‐chromen‐3‐yl)‐ethyl]‐1,3‐dihydro‐indol‐2‐one (3HOCE) and 3‐[2‐(8‐methoxy‐2‐oxo‐2H‐chromen‐3‐yl)‐2‐oxo‐ethylidene]‐1,3‐dihydro‐indol‐2‐one (3MOCE). Both compounds displayed a red shift with enhancement in solvent polarity. The larger excited state dipole moment indicated the more polar nature of the selected compounds in the excited state than in the ground state. Kinetic stability and chemical reactivity of the selected compounds were studied with help of the quantum chemical properties of the compounds such as frontier molecular orbital analysis using density functional theory calculations with B3LYP/6–311+G (d, p) basis sets. Molecular electrostatic potential, Mulliken charges, natural bond orbital, and nonlinear optical properties were further studied. NBO analysis showed proton transfer within the selected donor–acceptor, depicting the large energy of stabilization for the compounds. The calculated Fukui function inferred the local softness and electrophilicity indices of used solute compounds.

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Section: Resultssupporting

confidence: 92%

Section: Resultsmentioning

confidence: 74%

V ((), r) = \sum ([], \frac{Z_{R}}{R_{A} - r}) - \int ([], \frac{ρ (r^{'})}{r^{'} - r})

where Z R charge of nucleus A located at R A ρ ( r ′) electron density function of the solute r ′ integration variable of dummy. …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

2020

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“…Additionally, the energy deviation between the two structures is 9.95 kcal/mol. With the addition of two diffusion functions, the 6-311++G(d,p) basis set can better represent the electron distributions [30], hence, it was chosen for the current study. The van der Waals (VDW) radii for fluorine and hydrogen are 1.2 and 1.47 Å, respectively [31].…”

Section: Methodsmentioning

confidence: 99%

Molecular interactions between 1-butyl-3-methylimidazolium tetrafluoroborate and model naphthenic acids: A DFT study

Visscher

Gates

2017

Journal of Molecular Liquids

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A density functional theory study was performed to investigate the interactions between 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF 4 ]) and six different model naphthenic acids (NAs). Natural bond orbital, atoms in molecules, noncovalent interactions, HOMO-LUMO overlap integral, and electron density difference were analyzed. The analysis informs on the use of ionic liquids as solvents for the removal of NAs from crude oil. The main extraction mechanism for NAs without long alkyl chain is hydrogen bonding, whereas van der Waals interaction and hydrogen bonding are the dominant extraction mechanisms for NAs with long alkyl chain. F···H hydrogen bonding is the strongest hydrogen bond, and O···H is the second strongest for all the interactions. NAs with polycyclic hydrocarbons or multiple carboxylic groups have larger total interaction energies than those with monocyclic hydrocarbons and one carboxylic group. The results indicate that 

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Fe₃O₄ Nanoparticles Catalyzed Tandem Synthesis of Fluorescent 3‐(4,5‐diaryl‐1H‐imidazol‐2‐yl) quinoline‐2‐amines: Solvatochromic, DFT and Biological Studies

Bheemayya,

Kamble,

Sannaikar

et al. 2023

ChemistrySelect

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In the present work, Fe3O4 nanoparticles were prepared by the co‐precipitation method and employed as effective nanocatalysts in the tandem synthesis of 3‐(4,5‐diaryl‐1H‐imidazol‐2‐yl)quinolin‐2‐amines. An effective multicomponent reaction is plighted for 2‐chloroquinoline‐3‐carbaldehydes and substituted benzils to obtain novel heterocycles 3‐(4,5‐diaryl‐1H‐imidazol‐2‐yl)quinolin‐2‐amines. These molecules are fluorescent and hence for proper understanding of optical behaviour, solvatochromic and DFT studies were carried out. Also, the optical and energy bandgaps were calculated. Molecular docking studies manifested the strong binding affinities by these compounds at the active site of the Candida albicans dihydrofolate reductase enzyme (PDB ID: 1AI9) and Novobiocin (PDB ID: 4URO) with excellent C‐score values. Antimicrobial activity screening results have shown remarkable activity against Escherichia coli with appreciable MIC values and hence noteworthy action has been demonstrated against this bacterium. The zones of inhibition for some of the target compounds are also good against gram positive Staphylococcus aureus exhibiting excellent activity.

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DFT/ and TD-DFT/PCM calculations of molecular structure, spectroscopic characterization, NLO and NBO analyses of 4-(4-chlorophenyl) and 4-[4-(dimethylamino) phenyl]-2-oxo-1,2,5,6-tetrahydrobenzo[ h ]quinoline-3-carbonitrile dyes

Cited by 43 publications

References 59 publications

Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

Molecular interactions between 1-butyl-3-methylimidazolium tetrafluoroborate and model naphthenic acids: A DFT study

Fe₃O₄ Nanoparticles Catalyzed Tandem Synthesis of Fluorescent 3‐(4,5‐diaryl‐1H‐imidazol‐2‐yl) quinoline‐2‐amines: Solvatochromic, DFT and Biological Studies

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DFT/ and TD-DFT/PCM calculations of molecular structure, spectroscopic characterization, NLO and NBO analyses of 4-(4-chlorophenyl) and 4-[4-(dimethylamino) phenyl]-2-oxo-1,2,5,6-tetrahydrobenzo[ h ]quinoline-3-carbonitrile dyes

Cited by 43 publications

References 59 publications

Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

Molecular interactions between 1-butyl-3-methylimidazolium tetrafluoroborate and model naphthenic acids: A DFT study

Fe3O4 Nanoparticles Catalyzed Tandem Synthesis of Fluorescent 3‐(4,5‐diaryl‐1H‐imidazol‐2‐yl) quinoline‐2‐amines: Solvatochromic, DFT and Biological Studies

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Fe₃O₄ Nanoparticles Catalyzed Tandem Synthesis of Fluorescent 3‐(4,5‐diaryl‐1H‐imidazol‐2‐yl) quinoline‐2‐amines: Solvatochromic, DFT and Biological Studies