The effects of halogen substituents on the catalytic oxidation of benzylalcohols in the presence of dinuclear oxidovanadium(IV) complex

Bikas, Rahman; Shahmoradi, Elaheh; Noshiranzadeh, Nader; Emami, Marzieh; Reinoso, Santiago

The effects of halogen substituents on the catalytic oxidation of benzylalcohols in the presence of dinuclear oxidovanadium(IV) complex

dc.contributor.author	Bikas, Rahman
dc.contributor.author	Shahmoradi, Elaheh
dc.contributor.author	Noshiranzadeh, Nader
dc.contributor.author	Emami, Marzieh
dc.contributor.author	Reinoso, Santiago
dc.contributor.department	Ciencias	es_ES
dc.contributor.department	Zientziak	eu
dc.contributor.department	Institute for Advanced Materials and Mathematics - INAMAT2	en
dc.date.accessioned	2024-08-26T06:16:40Z
dc.date.available	2024-08-26T06:16:40Z
dc.date.issued	2017
dc.date.updated	2024-08-23T12:04:39Z
dc.description.abstract	A new dinuclear complex of oxidovanadium(IV), namely [(VO)2(HL)(l-O)] (1), has been synthesized by the reaction of VO(acac)2 with the heptadentate N4O3-donor Schiff base ligand, 2-(5-Bromo-2-hydroxyphenyl)-1,3-bis(2-(5-bromo-2-hydroxybenzylideneamino)ethyl)imidazolidine (H3L). The complex has been characterized by elemental analysis, spectroscopic methods and single-crystal X-ray diffraction. The latter technique revealed that the vanadium ions have distorted octahedral geometry and are connected together by oxido and phenolic oxygen atoms. The bridging oxido ligand shares the equatorial positions of the two metal centers while the oxygen atom of the bridging phenol group connects the axial positions. The catalytic activity of this complex has been tested for the oxidation of some benzyl alcohol derivatives by using H2O2 as a green oxidant. In order to maximize the yields, the effects of various influential parameters in catalytic reactions such as the oxidant-to-substrate molar ratio, the temperature and the solvent, were studied. Moreover, the electronic and steric effects of halogen substituents on the phenyl group of the substrate were also explored by analyzing the oxidation of benzyl alcohol derivatives with F, Cl and Br atoms in the relative para-position (electronic effect), and of another set of substrates with a Cl substituent in relative ortho-, meta, and para-positions (steric effect). The results of these catalytic studies show that complex 1 catalyzes the oxidation of benzyl alcohol derivatives to the corresponding benzaldehydes with little amounts of the benzoic acid being detectable in the reaction mixture. Both the reaction conditions and the substituents on the phenyl group of the benzyl alcohols affect the selectivity and the activity of this catalytic system.	en
dc.description.sponsorship	The authors are grateful to the University of Zanjan for financial support of this study. S.R. acknowledges financial support from the program "Ayudas para la Captación del Talento Adscritas a los Institutos de Investigación de la Universidad Pública de Navarra" funded by a collaboration agreement with Obra Social la Caixa and Fundación Caja Navarra.
dc.format.mimetype	application/pdf	en
dc.identifier.citation	Bikas, R., Shahmoradi, E., Noshiranzadeh, N., Emami, M., Reinoso, S. (2017) The effects of halogen substituents on the catalytic oxidation of benzylalcohols in the presence of dinuclear oxidovanadium(IV) complex. Inorganica Chimica Acta, 466, 100-109. https://doi.org/10.1016/j.ica.2017.05.049
dc.identifier.doi	10.1016/j.ica.2017.05.049
dc.identifier.issn	0020-1693
dc.identifier.uri	https://academica-e.unavarra.es/handle/2454/51409
dc.language.iso	eng
dc.publisher	Elsevier
dc.relation.ispartof	Inorganica Chimica Acta 466, (2017), 100–109
dc.relation.publisherversion	https://doi.org/10.1016/j.ica.2017.05.049
dc.rights	© 2017 Elsevier B.V. This manuscript version is made available under the CC-BY-NC-ND 4.0.
dc.rights.accessRights	info:eu-repo/semantics/openAccess
dc.rights.uri	https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subject	Dinuclear vanadium complex	en
dc.subject	Crystal structure	en
dc.subject	Oxidation of alcohols	en
dc.subject	Catalyst	en
dc.subject	Imidazolidine ligand	en
dc.title	The effects of halogen substituents on the catalytic oxidation of benzylalcohols in the presence of dinuclear oxidovanadium(IV) complex	en
dc.type	info:eu-repo/semantics/article
dc.type.version	info:eu-repo/semantics/acceptedVersion
dspace.entity.type	Publication
relation.isAuthorOfPublication	46bbf241-764d-4c78-9667-4c307cf84092
relation.isAuthorOfPublication.latestForDiscovery	46bbf241-764d-4c78-9667-4c307cf84092