Synthesis, characterization and biological studies of a charge transfer complex: 2-Aminopyridinium-4-methylbenzenesulfonate

Vadivelan, Ganesan; Murugesan, Venkatesan; Sekar, M.

doi:10.1016/j.saa.2015.03.045

Cited by 18 publications

(3 citation statements)

References 22 publications

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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%

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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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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“…In addition, pyridine and oxime compounds have been selected particularly for their ability to easily transfer the electrons of nitrogen atoms participating in the aromatic ring and C=N groups into the donor-acceptor system. [6][7][8][9][10][11] Due to their high levels of antibacterial properties and bioactive multizones, nitrogenous organic or inorganic compounds are reported to have positive effects on Escherichia coli. 12 The reason for the investigation of E. coli pathogens in molecular-docking studies is this bacterium's resistance against some medications and its high binding capacity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystallographic Structure, Hirshfeld Surface Analysis, Drug-likeness Properties and Molecular Docking Studies of New Oxime-pyridine Compounds

Topal

2021

ACSi

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A detailed description of the two new pyridine ligands, (2E,3Z)-3-[2-(3-chloropyridin-2-yl)hydrazinylidene]-N-hydroxybutan-2-imine and 3-chloro-2-{(2Z)-2-[1-(4 nitrophenyl)ethylidene]hydrazinyl}, is reported. The synthesized compounds were characterized by spectroscopic studies, spectral features were performed by TD-DFT calculations. New-generation pyridine ligand of HL2 was also determinate by single-crystal X-ray diffraction and Hirshfeld surface analysis with two-dimensional fingerprint plots was used to analyze intermolecular interactions in crystals. Molecular-docking was performed to investigate the binding areas of chemical compounds, and the results showed the inhibitory activity of the studied HL1 and HL2 against E. coli. The results of the current study revealed the drug-likeness and bioactive properties of the ligands.

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“…e synthesis and characterization of new hydrogen-bonded charge-transfer (HB-CT) complexes that have biological activities have attracted significant research interest in recent years [1][2][3]. is interest is largely due to the significant role that HB-CT complexes play in biological systems as antibacterial and antifungal compounds as well as the DNA binding these complexes exhibit [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Biological Evaluation of a New Hydrogen-Bonded Charge-Transfer Complex of 2-Amino-4-methoxy-6-methylpyrimidine

Alghanmi

2019

Journal of Chemistry

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A new hydrogen-bonded charge-transfer (HB-CT) complex formed between the donor 2-amino-4-methoxy-6-methylpyrimidine (AMMP) and the π-acceptor 2,5-dihydroxy-p-benzoquinone (DHBQ) was investigated in both solid and solution states. The investigation was conducted using UV-Vis, CHN, FTIR, 1H NMR, XRD, and TG-DTA analyses. The molecular composition of the CT complex in MeOH was found to be 1 : 1. The formation constant (KCT), molecular extinction coefficient (ε), and several other spectroscopic physical parameters were evaluated at different temperatures. The thermodynamic properties of the CT interaction in MeOH were studied by calculating the enthalpy (ΔH°), entropy (ΔS°), and free energy (ΔG°). The thermodynamic parameters indicated that van der Waals interactions and hydrogen bonding occur between AMMP and DHBQ in MeOH. The CHN, FTIR, and TG-DTA measurements confirmed that the solid HB-CT complex forms in a 2 : 1 ratio, i.e., [(AMMP)2(DHBQ)], and exhibits high stability. Moreover, XRD analysis was used to establish that the mean particle size of the complex is 23 nm. Finally, the solid HB-CT complex was screened for its antibacterial, antifungal, and antioxidant activities. It shows good activity against various bacterial and fungal species. Furthermore, the HB-CT complex exhibits good DPPH scavenging activity.

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Synthesis, characterization and biological studies of a charge transfer complex: 2-Aminopyridinium-4-methylbenzenesulfonate

Cited by 18 publications

References 22 publications

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

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

Synthesis, Crystallographic Structure, Hirshfeld Surface Analysis, Drug-likeness Properties and Molecular Docking Studies of New Oxime-pyridine Compounds

Synthesis, Characterization, and Biological Evaluation of a New Hydrogen-Bonded Charge-Transfer Complex of 2-Amino-4-methoxy-6-methylpyrimidine

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