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Open AccessArticle

Peroxidative Oxidation of Alkanes and Alcohols under Mild Conditions by Di- and Tetranuclear Copper (II) Complexes of Bis (2-Hydroxybenzylidene) Isophthalohydrazide

1
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal
2
Chemical Engineering Departament, Instituto Superior de Engenharia de Lisboa, Instituto Politécnico de Lisboa, R. Conselheiro Emídio Navarro, 1, 1959-007 Lisboa, Portugal
3
National Laboratory for Molecular Sciences, Center for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(10), 2699; https://doi.org/10.3390/molecules23102699
Received: 27 September 2018 / Revised: 13 October 2018 / Accepted: 15 October 2018 / Published: 19 October 2018
(This article belongs to the Special Issue Metal Complexes of Biological Ligands)
Bis(2-hydroxybenzylidene)isophthalohydrazide (H4L) has been used to synthesize the dinuclear [Cu2(1κNO2:2κN′O′2-H2L)(NO3)2(H2O)2] (1) and the tetranuclear [Cu4(μ-1κNO2:2κN′O2-H2L)2(μ-NO3)2(H2O)4]·2C2H5OH (2) complexes. The solvent plays an important role in determining the ligand behaviour in the syntheses of the complexes. An ethanol-acetonitrile mixture of solvents favours partials enolization in the case of 2. Both complexes have been characterized by elemental analysis, infrared radiation (IR), single crystal X-ray crystallography and electrochemical methods. The variable temperature magnetic susceptibility measurements of 2 show strong antiferromagnetic coupling between the central nitrato-bridged Cu (II) ions. The catalytic activity of both 1 and 2 has been screened toward the solvent-free microwave-assisted oxidation of alcohols and the peroxidative oxidation of alkanes under mild conditions. Complex 1 exhibits the highest activity for both oxidation reactions, leading selectively to a maximum product yield of 99% (for the 1-phenylethanol oxidation after 1 h without any additive) and 13% (for the cyclohexane oxidation to cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone after 3 h). View Full-Text
Keywords: Cu (II) complexes; microwave assisted oxidation of alcohols; oxidation of alkanes; solvent free process; magnetism Cu (II) complexes; microwave assisted oxidation of alcohols; oxidation of alkanes; solvent free process; magnetism
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Sutradhar, M.; Alegria, E.C.; Guedes da Silva, M.F.C.; Liu, C.-M.; Pombeiro, A.J.L. Peroxidative Oxidation of Alkanes and Alcohols under Mild Conditions by Di- and Tetranuclear Copper (II) Complexes of Bis (2-Hydroxybenzylidene) Isophthalohydrazide. Molecules 2018, 23, 2699.

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