Green electrochemical strategy for one-step synthesis of new catechol derivatives

Toghan, Arafat; Abo‐Bakr, Ahmed M.; Rageh, H.M.; Abd-Elsabour, Mohamed

doi:10.1039/c9ra01206k

Cited by 19 publications

(25 citation statements)

References 40 publications

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“…The shift to a short wavenumber (red-shift) and the broadness of these bands confirmed the formation of a cyclized product between catechol and semicarbazide. 7,8,10,13,17,19,22,23 Furthermore, the disappearance of semicarbazide and catechol bands at 2920 cm −1 , 2868 cm −1 , and 2670 cm −1 in the spectrum of product 9 is referred to as the cyclization between catechol and semicarbazide to form the new product. 8–10,13,15,17,19,23…”

Section: Resultsmentioning

confidence: 99%

“…7,8,10,13,17,19,22,23 Furthermore, the disappearance of semicarbazide and catechol bands at 2920 cm −1 , 2868 cm −1 , and 2670 cm −1 in the spectrum of product 9 is referred to as the cyclization between catechol and semicarbazide to form the new product. 8–10,13,15,17,19,23…”

Section: Resultsmentioning

confidence: 99%

“…The shift to long wavenumber and sharpness of the band at 519 cm −1 could be assigned to the N–H deformation of the cyclized ring formed in the product ( 9 ). 8–10,13,15,17,19,23…”

Section: Resultsmentioning

confidence: 99%

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Green electro-organic synthesis of a novel catechol derivative based on o-benzoquinone nucleophilic addition

et al. 2023

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Green electro-organic synthesis of a novel catechol derivative based on o-benzoquinone nucleophilic addition

et al. 2023

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“…SS316 steel alloy is vulnerable to harsh circumstances such as acidic or saline solutions [ 3 ]. Numerous approaches have been applied for the protection of these alloys from serious corrosion issues according to the economic aspects and service type [ 4 , 5 , 6 ]. The corrosion is an electrochemical process in which anodic and cathodic half-processes occur with matching kinetics.…”

Section: Introductionmentioning

confidence: 99%

Preparation, Characterization, and Evaluation of Macrocrystalline and Nanocrystalline Cellulose as Potential Corrosion Inhibitors for SS316 Alloy during Acid Pickling Process: Experimental and Computational Methods

et al. 2021

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Converting low-cost bio-plant residuals into high-value reusable nanomaterials such as microcrystalline cellulose is an important technological and environmental challenge. In this report, nanocrystalline cellulose (NCC) was prepared by acid hydrolysis of macrocrystalline cellulose (CEL). The newly synthesized nanomaterials were fully characterized using spectroscopic and microscopic techniques including FE-SEM, FT-IR, TEM, Raman spectroscopy, and BET surface area. Morphological portrayal showed the rod-shaped structure for NCC with an average diameter of 10–25 nm in thickness as well as length 100–200 nm. The BET surface area of pure CEL and NCC was found to be 10.41 and 27 m2/g, respectively. The comparative protection capacity of natural polymers CEL and NCC towards improving the SS316 alloy corrosion resistance has been assessed during the acid pickling process by electrochemical (OCP, PDP, and EIS), and weight loss (WL) measurements. The outcomes attained from the various empirical methods were matched and exhibited that the protective efficacy of these polymers augmented with the upsurge in dose in this order CEL (93.1%) < NCC (96.3%). The examined polymers display mixed-corrosion inhibition type features by hindering the active centers on the metal interface, and their adsorption followed the Langmuir isotherm model. Surface morphology analyses by SEM reinforced the adsorption of polymers on the metal substrate. The Density Functional Theory (DFT) parameters were intended and exhibited the anti-corrosive characteristics of CEL and NCC polymers. A Monte Carlo (MC) simulation study revealed that CEL and NCC polymers are resolutely adsorbed on the SS316 alloy surface and forming a powerful adsorbed protective layer.

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“…22,23 Compounds such as catechols, aminoanilines and aminophenols are readily oxidized and reduced in low potentials through a semireversible two-electron process, in which Ip C /Ip A is close to 1 for the proposed redox couples. [24][25][26][27] However, the cyclic voltammograms (CV) of pyrazoles show a high oxidation potential and lack of reduction potential. 28 This means that the oxidized forms of pyrazoles do not have enough stability on the electrolysis timescale when Ip C /Ip A approaches zero, and there would be rapid solvolysis or polymerization.…”

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confidence: 99%

Electrochemically Catalyzed N–N Coupling and Ring Cleavage Reaction of 1H-Pyrazoles

Zandi¹,

Sharafi‐Kolkeshvandi²,

Nikpour³

2021

Synthesis

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The electrocatalyzed N–N coupling and ring cleavage reaction of 3-methyl-, 3,5-dimethyl-, 3-methyl-5-phenyl- and 3,5-diphenyl-1H-pyrazole was investigated and led to the electro-organic synthesis of new heterocyclic compounds. The results revealed that electrochemically produced 1H-pyrazoleox plays the role of acceptor in a reaction with the starting molecule via a N–N coupling and ring cleavage reaction of pyrazoles. The proposed reaction sequence consists of anodic oxidation, dimerization, rearrangement and reduction. The electrochemically catalyzed reactions were accomplished under constant-current and constant-potential conditions using an undivided electrochemical cell with the advantages of mild reaction conditions, remarkable yields and environmental compatibility.

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Green electrochemical strategy for one-step synthesis of new catechol derivatives

Abstract: In this paper, we present promising results in the green electrochemical oxidation of catechol in the presence of three different thiol nucleophiles at the surface of a glassy carbon electrode in an aqueous solution using cyclic voltammetry (CV).

Cited by 19 publications

References 40 publications

Green electro-organic synthesis of a novel catechol derivative based on o-benzoquinone nucleophilic addition

Green electro-organic synthesis of a novel catechol derivative based on o-benzoquinone nucleophilic addition

Preparation, Characterization, and Evaluation of Macrocrystalline and Nanocrystalline Cellulose as Potential Corrosion Inhibitors for SS316 Alloy during Acid Pickling Process: Experimental and Computational Methods

Electrochemically Catalyzed N–N Coupling and Ring Cleavage Reaction of 1H-Pyrazoles

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