Computational study on intermolecular charge transfer complex of 2,2′-bipyridine with picric acid: TD-DFT, NBO and QTAIM analysis

Amirat, Samia; Fatiha, Madi; Bououdina, M.; Gheid, Abdelhak; Zaboub, Amal; Leila, Nouar; Merdès, Rachid

doi:10.1088/2053-1591/ab1507

Cited by 6 publications

(3 citation statements)

References 49 publications

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“…The frontier molecular orbital diagram is a powerful tool in explaining the chemical reactivity and kinetic stability of the molecule [2]. Figure 2 represents the occupied orbital (HOMO) and virtual orbital (LUMO) of complex in the gas phase.…”

Section: Resultsmentioning

confidence: 99%

Interaction between Picric Acid and 5-aminoquinoline: A Theoretical Study

Pandey

Mehata

Pant

2021

Jour. Atom. Mol. Conden. Matt. Nano Physics

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In the present work,density functional theory and time-dependent density functional theory were employed to investigate the hydrogen-bonded charge transfer complex of 5-aminoquinoline (5AQ) and picric acid (PA) at B3LYP/6-31G(d,p) level in the gas phase as well as CHCl 3 . The geometrical parameters, optimization energies, interaction energies, frontier molecular orbitals (FMOs), and ground-state dipole moment were considered, which supported the stability of the complex. Hence, the theoretical study of the 5AQ-PA complex provides valuable information about its molecular structure, possible interaction sites and electronically excited states.

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Section: Resultsmentioning

confidence: 99%

Interaction between Picric Acid and 5-aminoquinoline: A Theoretical Study

Pandey

Mehata

Pant

2021

Jour. Atom. Mol. Conden. Matt. Nano Physics

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“…Studies on the proton transfer between pyridine derivatives and various organic acids have been carried out in recent years (Drichko et al, 1999;Majerz & Koll, 2004;Majerz et al, 2005;Khan et al, 2011;Stilinovic ´& Kaitner, 2012;Seaton et al, 2013;Smith & Wermuth, 2013b;Thomas et al, 2013;Khalib et al, 2014;Lemmerer et al, 2015;Modec, 2015;Gaballa & Amin, 2015;Koeppe et al, 2017;Tanaka & Matsushita, 2017;Foretic et al, 2018;Amirat et al, 2019;Ma et al, 2019;de Carvalho et al, 2021;Stevens, 2022). Among these compounds, aminopyridine as a proton acceptor has been used to form proton-transfer salts with carboxylic acids and other acids as proton donors (Nazari et al, 2009;Vadivelan et al, 2015;Murugesan et al, 2015;Prakash et al, 2018;Al-Ahmary et al, 2018;Srijana et al, 2022Srijana et al, , 2023.…”

Section: Introductionmentioning

confidence: 99%

“…The reaction stoichiometries, the formation constants (K CT ) and the molar extinction coefficients (" CT ) of 1-3 were obtained using the Benesi-Hildebrand equation (Adam, 2013). Theoretical computations using density functional theory (DFT) with the B3LYP/6-31G(d,p) basis set were employed to investigate the molecular properties of the title protontransfer salts, including optimization of the structure, molecular electrostatic potential (MEP) and the HOMO and LUMO (HOMO is the highest occupied molecular orbital and LUMO is the lowest unoccupied molecular orbital) (Thangarasu et al, 2018;Amirat et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Proton-transfer salts of diphenylphosphinic acid with substituted 2-aminopyridine: crystal structure, spectroscopic and DFT studies

Yuan

Zhang

et al. 2023

Acta Crystallogr C

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Three proton-transfer salts of diphenylphosphinic acid (DPPA) with 2-amino-5-(X)-pyridine (AMPY, X = Cl, CN or CH3), namely, 2-amino-5-chloropyridinium diphenylphosphinate, C5H6ClN2 +·C12H10O2P− (1, X = Cl), 2-amino-5-cyanopyridinium diphenylphosphinate, C6H6N3 +·C12H10O2P− (2, X = CN), and 2-amino-5-methylpyridinium diphenylphosphinate, C6H9N2 +·C12H10O2P− (3, X = CH3), have been synthesized and characterized by FT–IR and 1H NMR spectroscopy, and X-ray crystallography. The crystal structures of compounds 1–3 were determined in the space group P\overline{1} for 1 and 2, and C2/c for 3. All three compounds contain N—H...O hydrogen-bonding interactions due to proton transfer from the O=P—OH group of DPPA as donor to the pyridine N atom of AMPY as acceptor. The proton transfer of compounds 1–3 was also verified by 1H NMR and FT–IR spectroscopy. The stoichiometry of all three proton-transfer salts was determined to be 1:1 and the Benesi–Hildebrand equation was applied to determine the formation constant (K CT) and the molar extinction coefficient (ɛCT) in each case. Theoretical density functional theory (DFT) calculations were performed to investigate the optimized geometries, the molecular electrostatic potentials (MEP) and the highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO) of all three proton-transfer salts. The results showed good agreement between the experimental data and the DFT computational analysis.

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