Copper(II) complex of N,N´-bis-(benzimidazol-2-yl-methyl)-hexane-1,6-dicarboxamide ligand: synthesis, structure and catalytic oxidation of amines in ionic liquid
{"title":"Copper(II) complex of N,N´-bis-(benzimidazol-2-yl-methyl)-hexane-1,6-dicarboxamide ligand: synthesis, structure and catalytic oxidation of amines in ionic liquid","authors":"Gauri Ahuja, Kuldeep Mahiya","doi":"10.1007/s11243-023-00566-3","DOIUrl":null,"url":null,"abstract":"<div><p>A new copper(II) complex, [Cu(L)NO<sub>3</sub>]NO<sub>3</sub>·2H<sub>2</sub>O, has been synthesized with <i>N</i>, <i>N'</i>-<i>bis</i>-(benzimidazol-2-yl-methyl)-hexane-1,6-dicarboxamide as a ligand, L = GBSA (Ahuja and Mathur in Spectrochim Acta Part A 83:180–186, 2011). The single-crystal X-ray structure characterization confirms that copper(II) ion in the complex possesses a distorted penta-coordinate geometry with one of the nitrate anions bound to copper(II) as a monodentate ligand. The N<sub>2</sub>O<sub>2</sub> equatorial plane of the copper(II) complex comprises of carbonyl oxygen atom (O1), nitrate oxygen atom (O3) and two benzimidazole nitrogen atom (N1,N4), while the axial position is occupied by oxygen atom (O2) of amide carbonyl. Low-temperature EPR study indicates distorted tetragonal geometry, while cathodic <i>E</i><sub>1/2</sub> value indicates stabilization of copper in + 2 oxidation state in solution. TGA data demonstrated thermal decomposition pattern of the complex. The complex was studied as a catalyst for the oxidation of aromatic and aliphatic primary and secondary amines in ionic liquid, [BMIM][BF<sub>4</sub>] as a solvent and TBHP as an external source of oxygen at 45–50 °C, affording good yields under mild conditions. Products formed were analyzed by GCMS.</p></div>","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2023-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11243-023-00566-3","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A new copper(II) complex, [Cu(L)NO3]NO3·2H2O, has been synthesized with N, N'-bis-(benzimidazol-2-yl-methyl)-hexane-1,6-dicarboxamide as a ligand, L = GBSA (Ahuja and Mathur in Spectrochim Acta Part A 83:180–186, 2011). The single-crystal X-ray structure characterization confirms that copper(II) ion in the complex possesses a distorted penta-coordinate geometry with one of the nitrate anions bound to copper(II) as a monodentate ligand. The N2O2 equatorial plane of the copper(II) complex comprises of carbonyl oxygen atom (O1), nitrate oxygen atom (O3) and two benzimidazole nitrogen atom (N1,N4), while the axial position is occupied by oxygen atom (O2) of amide carbonyl. Low-temperature EPR study indicates distorted tetragonal geometry, while cathodic E1/2 value indicates stabilization of copper in + 2 oxidation state in solution. TGA data demonstrated thermal decomposition pattern of the complex. The complex was studied as a catalyst for the oxidation of aromatic and aliphatic primary and secondary amines in ionic liquid, [BMIM][BF4] as a solvent and TBHP as an external source of oxygen at 45–50 °C, affording good yields under mild conditions. Products formed were analyzed by GCMS.
期刊介绍:
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
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