Intramolecular interactions, isomerization and vibrational frequencies of two paracetamol analogues: A spectroscopic and a computational approach

Viana, Rommel B.; Ribeiro, Gabriela L.O.; Santos, Sinara F.F. dos; Quintero, David E.; Viana, Anderson B.; Silva, Albérico Borges Ferreira da; Moreno-Fuquen, Rodolfo

doi:10.1016/j.saa.2016.02.037

Cited by 12 publications

(3 citation statements)

References 100 publications

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“…Electrostatic potential maps (ESPs) are seen in Figure . It should be highlighted that a higher electron density in the red color zone is connected to the nucleophilic region . Due to the reduction of electrons, the blue area is the electrophilic site .…”

Section: Resultsmentioning

confidence: 99%

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Expired Antifungal Drugs as Effective Corrosion Inhibitors for Carbon Steel in 1 M HCl Solution: Practical and Theoretical Approaches

Abdallah,

Soliman,

Alfakeer

et al. 2023

ACS Omega

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The anticorrosion potency of two expired antifungal drugs, namely, bifonazole (BIF) and terconazole (TER), for X65 carbon steel (X65CS) in a 1.0 M HCl solution was estimated using practical and computational measurements. The results of all methods applied showed that the percentage of anticorrosive efficacy (% AE) increased for expired BIF and TER and reduced at elevated temperatures. The % AE values of expired BIF and TER (375 mg L −1 ) reached 92.08 and 94.19%, respectively, using polarization methods. The anticorrosion activities of the two expired drugs were interpreted based on their adsorption on the X65CS surface. The adsorption occurred according to the Langmuir isotherm model. The polarization results indicated that the expired drugs BIF and TER were mixed inhibitors. The impedance results showed a single capacitive loop, confirming that the charge transfer process controlled the corrosion of X65CS. Expired BIF and TER served as good pitting inhibitors by shifting the pitting potential to positive values. The thermodynamic functions of activation and adsorption were defined and explained. Density functional theory and Monte Carlo simulations were used to investigate the BIF and TER inhibitors. The theoretical parameters were consistent with the experimental results. The anticorrosion efficiencies determined using the various methods were in complete agreement.

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Section: Resultsmentioning

confidence: 99%

“…It should be highlighted that a higher electron density in the red color zone is connected to the nucleophilic region. 62 Due to the reduction of electrons, the blue area is the electrophilic site. 30 A nucleophilic site is located on the nitrogen and oxygen atoms for the TER inhibitor and on the nitrogen atom for BIF inhibitors.…”

Section: Resultsmentioning

confidence: 99%

Expired Antifungal Drugs as Effective Corrosion Inhibitors for Carbon Steel in 1 M HCl Solution: Practical and Theoretical Approaches

Abdallah,

Soliman,

Alfakeer

et al. 2023

ACS Omega

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“…In this sense, N-benzoyl-1,2,4-triazoles are amenable to further derivatization via palladium-catalyzed substitutions of the methylsulfanyl moiety (Liebeskind-Srogl cross-coupling) (Liebeskind & Srogl, 2002). Continuing our ongoing research toward the synthesis of biologically active N-heterocycles using green-chemistry tools (Moreno-Fuquen et al, 2014, 2015Viana et al, 2016;Castillo et al, 2018a), we envisioned that the regioselective N-acylation of 3-amino-5methylsulfanyl-1H-1,2,4-triazole, (1), with 2-fluorobenzoyl chloride, (2), might generate the amino-1,2,4-triazole (3) acylated on the triazolic ring, which upon microwave irradiation would provide the secondary amide (4) acylated on the exocyclic amine group via a Fries rearrangement under catalyst-and solvent-free conditions (Scheme 2). In the present work, the structures of the synthesized amides, the tautomerism and the mechanistic pathway were investigated using both theoretical studies and X-ray crystallography.…”

Section: Introductionmentioning

confidence: 99%

Catalyst- and solvent-free synthesis of 2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement: X-ray structural and theoretical studies

et al. 2019

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An efficient approach for the regioselective synthesis of (5-amino-3-methylsulfanyl-1H-1,2,4-triazol-1-yl)(2-fluorophenyl)methanone, C10H9FN4OS, (3), from the N-acylation of 3-amino-5-methylsulfanyl-1H-1,2,4-triazole, (1), with 2-fluorobenzoyl chloride has been developed. Heterocyclic amide (3) was used successfully as a strategic intermediate for the preparation of 2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide, C10H9FN4OS, (4), through a microwave-assisted Fries rearrangement under catalyst- and solvent-free conditions. Theoretical studies of the prototropy process of (1) and the Fries rearrangement of (3) to provide (4), involving the formation of an intimate ion pair as the key step, were carried out by density functional theory (DFT) calculations. The crystallographic analysis of the intermolecular interactions and the energy frameworks based on the effects of the different molecular conformations of (3) and (4) are described.

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Synthesis, characterisation and corrosion inhibitory study of Meldrum’s acid Thiosemicarbazone: Weight Loss, SEM-EDX and DFT

Idelfttri

Dzulkifli

Ash’ari

et al. 2023

Inorganic Chemistry Communications

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Intramolecular interactions, isomerization and vibrational frequencies of two paracetamol analogues: A spectroscopic and a computational approach

Cited by 12 publications

References 100 publications

Expired Antifungal Drugs as Effective Corrosion Inhibitors for Carbon Steel in 1 M HCl Solution: Practical and Theoretical Approaches

Expired Antifungal Drugs as Effective Corrosion Inhibitors for Carbon Steel in 1 M HCl Solution: Practical and Theoretical Approaches

Catalyst- and solvent-free synthesis of 2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement: X-ray structural and theoretical studies

Synthesis, characterisation and corrosion inhibitory study of Meldrum’s acid Thiosemicarbazone: Weight Loss, SEM-EDX and DFT

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