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Title: 4,6-Diacetyl Resorcinol Based Vanadium(V) Complexes: Reactivity and Catalytic Applications
Authors: Maurya, Mannar Ram
Jangra N.
Avecilla F.
Correia I.
Published in: European Journal of Inorganic Chemistry
Abstract: Four ONO donor ligands are isolated from the condensation of 4,6-diacetyl resorcinol with isonicotinoyl hydrazide (H2dar-inh, I), nicotinoyl hydrazide (H2dar-nah, II), benzoyl hydrazide (H2dar-bhz, III), and 2-furoyl hydrazide (H2dar-fah, IV) on refluxing in MeOH. The reaction of in situ generated aqueous K[H2VVO4] with ligands I–IV at neutral pH gives complexes [K(H2O)2][VO2(dar-inh)] (1), [K(H2O)2][VO2(dar-nah)] (2), [K(H2O)2][VO2(dar-bhz)] (3), and [K(H2O)2][VO2(dar-fah)] (4), respectively. The reaction of [VIVO(acac)2] (acac = acetylacetonato) with these ligands (I–IV) under aerobic conditions in methanol yields oxidomethoxidovanadium(V) complexes [VO(OMe)(MeOH)(dar-inh)] (5), [VO(OMe)(MeOH)(dar-nah)] (6), [VO(OMe)(MeOH)(dar-bhz)] (7), and [VO(OMe)(MeOH)(dar-fah)] (8). All the isolated complexes are characterized by elemental, thermal, electrochemical, and spectroscopic techniques [FTIR, UV/Vis, NMR (1H, 13C and 51V NMR)], and single-crystal X-ray diffraction analysis (for 1, 6, 7, and 8). X-ray analysis confirms the coordination of the ligands through Ophenolate, Nazomethine, and Oenolate to the metal center. In the molecular structure of [K(H2O)(EtOH)][VVO2(dar-inh)] (abbreviated as 1a where one molecule of water is replaced by EtOH), water molecules act as bridges between two K+ ions and the complex shows a dimeric structure due to the presence of electrostatic interactions between V=O oxygen atoms with K+ ions. These complexes are active catalysts for the oxidative bromination of thymol in the presence of KBr, HClO4, and H2O2 and give 2-bromothymol, 4-bromothymol, and 2,4-dibromothymol as major products. Complexes 1–4 were also tested as catalysts for the epoxidation of various alkenes (namely styrene, cyclohexene, cis-cyclooctene, 1-hexene, 1-octene, cyclohexenone, and trans-stilbene) with H2O2 in the presence of NaHCO3 as promoter, giving the corresponding epoxides selectively. © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Citation: European Journal of Inorganic Chemistry, 2019(2): 314-329
Issue Date: 2019
Publisher: Wiley-VCH Verlag
Keywords: Epoxidation of alkenes
Haloperoxidase models
Homogeneous catalysis
Oxidative bromination
Structure elucidation
ISSN: 14341948
Author Scopus IDs: 7005255411
Author Affiliations: Maurya, M.R., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247667, India
Jangra, N., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247667, India
Avecilla, F., Grupo Xenomar, Centro de Investigacións Científicas Avanzadas (CICA), Facultade de Ciencias, Universidade da Coruña, Campus de A Coruña, Coruña, 15071A, Spain
Correia, I., Centro de Química Estrutural, Instituto Superior Técnico, Universidade Lisboa, Lisboa, 1049-001, Portugal
Funding Details: 
Corresponding Author: Maurya, M.R.; Department of Chemistry, India; email:
Appears in Collections:Journal Publications [CY]

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