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Molecules 2016, 21(4), 425; doi:10.3390/molecules21040425

Aroylhydrazone Cu(II) Complexes in keto Form: Structural Characterization and Catalytic Activity towards Cyclohexane Oxidation

1
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal
2
Chemical Engineering Department, Instituto Superior de Engenharia da Lisboa, Instituto Politécnico de Lisboa, R. Conselheiro Emídio Navarro, 1959-007 Lisboa, Portugal
*
Authors to whom correspondence should be addressed.
Academic Editor: Sónia A. C. Carabineiro
Received: 27 January 2016 / Revised: 21 March 2016 / Accepted: 23 March 2016 / Published: 29 March 2016
(This article belongs to the Special Issue Coinage Metal (Copper, Silver, and Gold) Catalysis)
View Full-Text   |   Download PDF [1796 KB, uploaded 29 March 2016]   |  

Abstract

The reaction of the Schiff base (3,5-di-tert-butyl-2-hydroxybenzylidene)-2-hydroxybenzohydrazide (H3L) with a copper(II) salt of a base of a strong acid, i.e., nitrate, chloride or sulphate, yielded the mononuclear complexes [Cu(H2L)(NO3)(H2O)] (1), [Cu(H2L)Cl]·2MeOH (2) and the binuclear complex [{Cu(H2L)}2(µ-SO4)]·2MeOH (3), respectively, with H2L in the keto form. Compounds 13 were characterized by elemental analysis, Infrared (IR) spectroscopy, Electrospray Ionisation Mass Spectrometry (ESI-MS) and single crystal X-ray crystallography. All compounds act as efficient catalysts towards the peroxidative oxidation of cyclohexane to cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone, under mild conditions. In the presence of an acid promoter, overall yields (based on the alkane) up to 25% and a turnover number (TON) of 250 (TOF of 42 h−1) after 6 h, were achieved. View Full-Text
Keywords: O,N,O ligands; Cu(II) complex; X-ray structure; cyclohexane oxidation O,N,O ligands; Cu(II) complex; X-ray structure; cyclohexane oxidation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Sutradhar, M.; Alegria, E.C.B.A.; Guedes da Silva, M.F.C.; Martins, L.M.D.R.S.; Pombeiro, A.J.L. Aroylhydrazone Cu(II) Complexes in keto Form: Structural Characterization and Catalytic Activity towards Cyclohexane Oxidation. Molecules 2016, 21, 425.

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