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Imidazo[1,2-a]Pyridine Derivatives–Copper(II) Salts: Highly Effective In Situ Combination for Catecholase
Chemistry Africa Pub Date : 2023-03-25 , DOI: 10.1007/s42250-023-00650-2
Mohamed Moutaouakil , Cherif Abdelmjid , Othmane Roby , Said Tighadouini , Jamal Jamaleddine , Rafik Saddik

In this work, we were interested in the search for new catalysts for catecholase, whose principle is based on the oxidation reaction of catechol to o-quinone. In this context, a series of ligands derived from 2-phenylimidazo[1,2-a]pyridine-3-carbaldehy were synthesized; then, the complexes formed in situ between these ligands and copper(II) salts, namely Cu(CH3COO)2, CuSO4, Cu(NO3)2 and CuCl2 were examined for their catecholase activity. The kinetics of the reaction was followed by measuring the absorbance versus time with a UV-Vis spectrophotometer for one hour. Compared with other work done in the same framework, the results obtained in this study show that the copper(II)-ligand complexes studied possess excellent catalytic activities for the oxidation of catechol to o-quinone. In particular, the complexes formed between the ligands and the salts Cu(CH3COO)2 and CuSO4 show oxidation rates much higher than those found in the literature. On the other hand, the complexes formed between the ligands and Cu(NO3)2 and CuCl2 also catalyze the reaction, but with much lower oxidation rates than the former. The complex formed between Cu(CH3COO)2 and L1 (2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde) shows the highest catalytic activity with an oxidation rate of 260.41 µmol L−1 s−1, and the complex formed between L6 (6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde) and CuCl2 shows the lowest catalytic activity (43.4 µmol L−1 s−1). This study’s results also show that these complexes’ oxidation efficiency depends on several factors, namely the nature of the substituents on the ligands and the anions of the copper salts.



中文翻译:

咪唑并 [1,2-a] 吡啶衍生物 - 铜 (II) 盐:儿茶酚酶的高效原位组合

在这项工作中,我们感兴趣的是寻找新的儿茶酚酶催化剂,其原理是基于儿茶酚氧化反应生成醌。在此背景下,合成了一系列衍生自2-苯基咪唑并[1,2-a]吡啶-3-甲醛的配体;然后,在这些配体和铜(II)盐之间原位形成络合物,即Cu(CH 3 COO) 2、CuSO 4、Cu(NO 3 ) 2和CuCl 2检查了它们的儿茶酚酶活性。通过用紫外-可见分光光度计测量吸光度与时间的关系一小时来跟踪反应的动力学。与在同一框架内完成的其他工作相比,本研究获得的结果表明,所研究的铜 (II)-配体配合物对邻苯二酚氧化为邻苯二酚具有优异的催化活性具体而言,配体与盐 Cu(CH 3 COO) 2和 CuSO 4之间形成的络合物显示出比文献中发现的那些高得多的氧化速率。另一方面,配体与 Cu(NO 3 ) 2和 CuCl 2形成的配合物也催化反应,但氧化速率比前者低得多。Cu(CH 3 COO) 2和L 1 (2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde)之间形成的络合物显示出最高的催化活性,氧化速率为260.41 µmol L -1  s -1, L 6 (6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde) 和 CuCl 2之间形成的络合物显示出最低的催化活性 (43.4 µmol L −1  s −1). 这项研究的结果还表明,这些配合物的氧化效率取决于几个因素,即配体上取代基的性质和铜盐的阴离子。

更新日期:2023-03-26
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