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Synthesis of Cyano-Benzylidene Xanthene Synthons Using a Diprotic Brønsted Acid Catalyst, and Their Application as Efficient Inhibitors of Aluminum Corrosion in Alkaline Solutions

Novel cyano-benzylidene xanthene derivatives were synthesized using one-pot and condensation reactions. A diprotic Brønsted acid (i.e., oxalic acid) was used as an effective catalyst for the promotion of the synthesis process of the new starting xanthene–aldehyde compound. Different xanthene concent...

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Autores principales: Amin, Mohammed A., Mersal, Gaber A. M., El-Hendawy, Morad M., Shaltout, Abdallah A., Badawi, Ali, Boman, Johan, Gobouri, Adil A., Saracoglu, Murat, Kandemirli, Fatma, Boukherroub, Rabah, Ryl, Jacek, Khalifa, Mohamed E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457813/
https://www.ncbi.nlm.nih.gov/pubmed/36080500
http://dx.doi.org/10.3390/molecules27175733
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author Amin, Mohammed A.
Mersal, Gaber A. M.
El-Hendawy, Morad M.
Shaltout, Abdallah A.
Badawi, Ali
Boman, Johan
Gobouri, Adil A.
Saracoglu, Murat
Kandemirli, Fatma
Boukherroub, Rabah
Ryl, Jacek
Khalifa, Mohamed E.
author_facet Amin, Mohammed A.
Mersal, Gaber A. M.
El-Hendawy, Morad M.
Shaltout, Abdallah A.
Badawi, Ali
Boman, Johan
Gobouri, Adil A.
Saracoglu, Murat
Kandemirli, Fatma
Boukherroub, Rabah
Ryl, Jacek
Khalifa, Mohamed E.
author_sort Amin, Mohammed A.
collection PubMed
description Novel cyano-benzylidene xanthene derivatives were synthesized using one-pot and condensation reactions. A diprotic Brønsted acid (i.e., oxalic acid) was used as an effective catalyst for the promotion of the synthesis process of the new starting xanthene–aldehyde compound. Different xanthene concentrations (ca. 0.1–2.0 mM) were applied as corrosion inhibitors to control the alkaline uniform corrosion of aluminum. Measurements were conducted in 1.0 M NaOH solution using Tafel extrapolation and linear polarization resistance (LPR) methods. The investigated xanthenes acted as mixed-type inhibitors that primarily affect the anodic process. Their inhibition efficiency values were enhanced with inhibitor concentration, and varied according to their chemical structures. At a concentration of 2.0 mM, the best-performing studied xanthene derivative recorded maximum inhibition efficiency values of 98.9% (calculated via the Tafel extrapolation method) and 98.4% (estimated via the LPR method). Scanning electron microscopy (SEM) was used to examine the morphology of the corroded and inhibited aluminum surfaces, revealing strong inhibitory action of each studied compound. High-resolution X-ray photoelectron spectroscopy (XPS) profiles validated the inhibitor compounds’ adsorption on the Al surface. Density functional theory (DFT) and Monte Carlo simulations were applied to investigate the distinction of the anticorrosive behavior among the studied xanthenes toward the Al (111) surface. The non-planarity of xanthenes and the presence of the nitrile group were the key players in the adsorption process. A match between the experimental and theoretical findings was evidenced.
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spelling pubmed-94578132022-09-09 Synthesis of Cyano-Benzylidene Xanthene Synthons Using a Diprotic Brønsted Acid Catalyst, and Their Application as Efficient Inhibitors of Aluminum Corrosion in Alkaline Solutions Amin, Mohammed A. Mersal, Gaber A. M. El-Hendawy, Morad M. Shaltout, Abdallah A. Badawi, Ali Boman, Johan Gobouri, Adil A. Saracoglu, Murat Kandemirli, Fatma Boukherroub, Rabah Ryl, Jacek Khalifa, Mohamed E. Molecules Article Novel cyano-benzylidene xanthene derivatives were synthesized using one-pot and condensation reactions. A diprotic Brønsted acid (i.e., oxalic acid) was used as an effective catalyst for the promotion of the synthesis process of the new starting xanthene–aldehyde compound. Different xanthene concentrations (ca. 0.1–2.0 mM) were applied as corrosion inhibitors to control the alkaline uniform corrosion of aluminum. Measurements were conducted in 1.0 M NaOH solution using Tafel extrapolation and linear polarization resistance (LPR) methods. The investigated xanthenes acted as mixed-type inhibitors that primarily affect the anodic process. Their inhibition efficiency values were enhanced with inhibitor concentration, and varied according to their chemical structures. At a concentration of 2.0 mM, the best-performing studied xanthene derivative recorded maximum inhibition efficiency values of 98.9% (calculated via the Tafel extrapolation method) and 98.4% (estimated via the LPR method). Scanning electron microscopy (SEM) was used to examine the morphology of the corroded and inhibited aluminum surfaces, revealing strong inhibitory action of each studied compound. High-resolution X-ray photoelectron spectroscopy (XPS) profiles validated the inhibitor compounds’ adsorption on the Al surface. Density functional theory (DFT) and Monte Carlo simulations were applied to investigate the distinction of the anticorrosive behavior among the studied xanthenes toward the Al (111) surface. The non-planarity of xanthenes and the presence of the nitrile group were the key players in the adsorption process. A match between the experimental and theoretical findings was evidenced. MDPI 2022-09-05 /pmc/articles/PMC9457813/ /pubmed/36080500 http://dx.doi.org/10.3390/molecules27175733 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Amin, Mohammed A.
Mersal, Gaber A. M.
El-Hendawy, Morad M.
Shaltout, Abdallah A.
Badawi, Ali
Boman, Johan
Gobouri, Adil A.
Saracoglu, Murat
Kandemirli, Fatma
Boukherroub, Rabah
Ryl, Jacek
Khalifa, Mohamed E.
Synthesis of Cyano-Benzylidene Xanthene Synthons Using a Diprotic Brønsted Acid Catalyst, and Their Application as Efficient Inhibitors of Aluminum Corrosion in Alkaline Solutions
title Synthesis of Cyano-Benzylidene Xanthene Synthons Using a Diprotic Brønsted Acid Catalyst, and Their Application as Efficient Inhibitors of Aluminum Corrosion in Alkaline Solutions
title_full Synthesis of Cyano-Benzylidene Xanthene Synthons Using a Diprotic Brønsted Acid Catalyst, and Their Application as Efficient Inhibitors of Aluminum Corrosion in Alkaline Solutions
title_fullStr Synthesis of Cyano-Benzylidene Xanthene Synthons Using a Diprotic Brønsted Acid Catalyst, and Their Application as Efficient Inhibitors of Aluminum Corrosion in Alkaline Solutions
title_full_unstemmed Synthesis of Cyano-Benzylidene Xanthene Synthons Using a Diprotic Brønsted Acid Catalyst, and Their Application as Efficient Inhibitors of Aluminum Corrosion in Alkaline Solutions
title_short Synthesis of Cyano-Benzylidene Xanthene Synthons Using a Diprotic Brønsted Acid Catalyst, and Their Application as Efficient Inhibitors of Aluminum Corrosion in Alkaline Solutions
title_sort synthesis of cyano-benzylidene xanthene synthons using a diprotic brønsted acid catalyst, and their application as efficient inhibitors of aluminum corrosion in alkaline solutions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457813/
https://www.ncbi.nlm.nih.gov/pubmed/36080500
http://dx.doi.org/10.3390/molecules27175733
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