Diastereoselective electrochemical coupling of beta-nitrostyrenes using constant-current conditionsIUT file repository
The electrochemical coupling reactions of beta-nitrostyrene and 4-chloro-beta-nitrostyrene were reported. This is the first report on the electrochemical hydrodimerization of beta-nitrostyrenes. Moreover, the electrochemical processes were performed using the simplest conditions: constant-current (s...
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| Language: | English |
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Elsevier
2025-03-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715625000992 |
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| author | Hossein Tavakol Fatemeh Najafi Davood Nematollahi Arash Kazemi |
| author_facet | Hossein Tavakol Fatemeh Najafi Davood Nematollahi Arash Kazemi |
| author_sort | Hossein Tavakol |
| collection | DOAJ |
| description | The electrochemical coupling reactions of beta-nitrostyrene and 4-chloro-beta-nitrostyrene were reported. This is the first report on the electrochemical hydrodimerization of beta-nitrostyrenes. Moreover, the electrochemical processes were performed using the simplest conditions: constant-current (simpler than constant potential), simple and undivided electrochemical cell, employing non-expensive graphite and still electrodes, using green solvent (ethanol), and performing at room temperature. Using various cyclic voltammetry experiments, the effects of potential scan rate and pH on the electrochemical behavior of the reactant were investigated. Moreover, different reaction conditions such as pH, solvent, type of electrodes, and current density were optimized by examining the yield of the product. The optimized conditions were pH = 6, ethanol solvent, steel sheets as a cathode, graphite rod as an anode, and current density = 0.97 mA/cm2 (30 mA current). Moreover, using coulometry analysis, the number of exchanged electrons in this process was calculated to help find the possible mechanism. After the completion of the reactions, the structures of the products were confirmed using mass spectrometry, FT-IR, and NMR methods. It was found that only more thermodynamically stable meso configurations were produced, which makes the reaction diastereoselective. The plausible mechanism, which is obeyed from the EC electrochemical mechanism, was proposed for the two-electron transfer reaction. |
| format | Article |
| id | doaj-art-1a090204618d46de8716e9339d0d68d1 |
| institution | DOAJ |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-1a090204618d46de8716e9339d0d68d12025-08-20T02:47:39ZengElsevierResults in Chemistry2211-71562025-03-011410211610.1016/j.rechem.2025.102116Diastereoselective electrochemical coupling of beta-nitrostyrenes using constant-current conditionsIUT file repositoryHossein Tavakol0Fatemeh Najafi1Davood Nematollahi2Arash Kazemi3Department of Chemistry, Isfahan University of Technology, Isfahan 84156-83111, Iran; Corresponding author.Department of Chemistry, Isfahan University of Technology, Isfahan 84156-83111, IranFaculty of Chemistry, Bu-Ali-Sina University, Mahdiyeh St., Hamadan Zip Code 65174, IranDepartment of Chemistry, Isfahan University of Technology, Isfahan 84156-83111, IranThe electrochemical coupling reactions of beta-nitrostyrene and 4-chloro-beta-nitrostyrene were reported. This is the first report on the electrochemical hydrodimerization of beta-nitrostyrenes. Moreover, the electrochemical processes were performed using the simplest conditions: constant-current (simpler than constant potential), simple and undivided electrochemical cell, employing non-expensive graphite and still electrodes, using green solvent (ethanol), and performing at room temperature. Using various cyclic voltammetry experiments, the effects of potential scan rate and pH on the electrochemical behavior of the reactant were investigated. Moreover, different reaction conditions such as pH, solvent, type of electrodes, and current density were optimized by examining the yield of the product. The optimized conditions were pH = 6, ethanol solvent, steel sheets as a cathode, graphite rod as an anode, and current density = 0.97 mA/cm2 (30 mA current). Moreover, using coulometry analysis, the number of exchanged electrons in this process was calculated to help find the possible mechanism. After the completion of the reactions, the structures of the products were confirmed using mass spectrometry, FT-IR, and NMR methods. It was found that only more thermodynamically stable meso configurations were produced, which makes the reaction diastereoselective. The plausible mechanism, which is obeyed from the EC electrochemical mechanism, was proposed for the two-electron transfer reaction.http://www.sciencedirect.com/science/article/pii/S2211715625000992Electrochemical reactionBeta-nitrostyreneConstant-currentDiastereoselectiveDimerization |
| spellingShingle | Hossein Tavakol Fatemeh Najafi Davood Nematollahi Arash Kazemi Diastereoselective electrochemical coupling of beta-nitrostyrenes using constant-current conditionsIUT file repository Results in Chemistry Electrochemical reaction Beta-nitrostyrene Constant-current Diastereoselective Dimerization |
| title | Diastereoselective electrochemical coupling of beta-nitrostyrenes using constant-current conditionsIUT file repository |
| title_full | Diastereoselective electrochemical coupling of beta-nitrostyrenes using constant-current conditionsIUT file repository |
| title_fullStr | Diastereoselective electrochemical coupling of beta-nitrostyrenes using constant-current conditionsIUT file repository |
| title_full_unstemmed | Diastereoselective electrochemical coupling of beta-nitrostyrenes using constant-current conditionsIUT file repository |
| title_short | Diastereoselective electrochemical coupling of beta-nitrostyrenes using constant-current conditionsIUT file repository |
| title_sort | diastereoselective electrochemical coupling of beta nitrostyrenes using constant current conditionsiut file repository |
| topic | Electrochemical reaction Beta-nitrostyrene Constant-current Diastereoselective Dimerization |
| url | http://www.sciencedirect.com/science/article/pii/S2211715625000992 |
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