Synthesis, crystal structure and catalytic activity of a new Mo Schiff base complex with Mo histidine immobilized on Al-MCM-41 for oxidation of sulfides

Zamanifar, Elham; Farzaneh, Faezeh; Simpson, Jim; Maghami, Mahboobeh

doi:10.1016/j.ica.2014.01.028

Cited by 28 publications

(16 citation statements)

References 48 publications

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“…The NH stretching of the free ligand displaying at 3302 cm −1 disappeared in the spectrum of Fe 3 O 4 @SiO 2 ‐CPS‐L due to the ligand binding to the Fe 3 O 4 @SiO 2 ‐CPS via the N atom of the amide group . Fe 3 O 4 @SiO 2 ‐CPS‐L‐MoO 2 (EtOH) shows two characteristic bands at 923 and 943 cm −1 which can be assigned to symmetric and asymmetric vibrations of Mo = O (Figure f).…”

Section: Resultsmentioning

confidence: 99%

New magnetic supported hydrazone Schiff base dioxomolybdenum (VI) complex: An efficient nanocatalyst for epoxidation of cyclooctene and norbornene

Sarkheil

Lashanizadegan

2018

Applied Organom Chemis

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A new dioxomolybdenum (VI) complex with tridentate hydrazone Schiff base ligand (H2L) derived from 2‐hydroxy‐5‐nitrobenzaldehyde and benzhydrazide was synthesized and designated as [MoO2L (DMF)]·2H2O. The Fe3O4@SiO2‐CPS‐L‐MoO2 (EtOH) nanocatalyst was successfully prepared by grafting H2L ligand on modified Fe3O4 nanoparticles followed by reacting with MoO2 (acac)2. The complex and nanocatalyst were characterized by various techniques such as elemental analysis, mass, FT‐IR, UV–Vis, 1H NMR, 13C{1H}‐NMR, TGA, XRD, XPS, TEM, SEM and VSM. The catalytic activity of [MoO2L (DMF)]2H2O and Fe3O4@SiO2‐CPS‐L‐MoO2 (EtOH) were evaluated for the oxidation of various alkenes (cyclooctene, norbornene, cyclohexene, styrene and α‐methyl styrene) in the presence of tert‐butylhydroperoxide as oxidant. The results revealed that the catalysts were especially efficient for oxidation of cyclooctene and norbornene with 100% selectivity towards corresponding epoxide product. Fe3O4@SiO2‐CPS‐L‐MoO2 (EtOH) showed higher catalytic activity, shorter reaction time and higher turnover number (TON) compared with homogeneous complex [MoO2L (DMF)]·2H2O. Moreover, simple magnetic recovery from the reaction mixture and reuse for several times with no significant loss in activity were other advantages of the nanocatalyst.

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Section: Resultsmentioning

confidence: 99%

New magnetic supported hydrazone Schiff base dioxomolybdenum (VI) complex: An efficient nanocatalyst for epoxidation of cyclooctene and norbornene

Sarkheil

Lashanizadegan

2018

Applied Organom Chemis

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“…The ligand precursor derived from l ‐histidine ( S ‐H 2 his) and salicylaldehyde, ( S )‐2‐[(2‐hydroxylbenzylidene)amino]‐3‐(1 H ‐imidazol‐4‐yl)propanoic acid ( S ‐H 3 L), is an interesting multidentate ligand having four different kinds of potential donor groups, but it is, therefore, difficult to control the coordination modes on complexation to a certain metal ion. So far, a few V, Cu, Mo, and U complexes with the S ‐H 3 L anion have been reported, but no systematic study on the coordination properties of this ligand has been reported. Here, we reveal the functionality of histidine complexes originating from the coordination of the imidazole group.…”

Section: Introductionmentioning

confidence: 99%

Schiff Base Ligands Derived from l‐Histidine Methyl Ester: Characterization, Racemization, and Dimerization of Their Transition‐Metal Complexes

2018

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Reactions of methyl (S)‐2‐[(2‐hydroxybenzylidene)amino]‐3‐(1H‐imidazol‐4‐yl)propanoate (S‐H2LMe) and various transition‐metal(II) salts (MX2: M = Mn, Fe, Co, and Ni; X = ClO4, Cl, OAc, etc.) are examined. During the reactions with MnII and CoII salts, the MII ion is oxidized by air to form a cationic complex with two mono‐deprotonated ligands, [MIII(S‐HLMe)2]X [M, X = Mn, ClO4 (S‐1ClO4); Co, ClO4 (S‐3ClO4); and Co, Cl (S‐3Cl)], where (S‐HLMe)– is coordinated to a MIII center in a tridentate κ3O,N,N′ mode with a mer configuration. In contrast, the NiII ion is not oxidized; only one of the ligands is deprotonated to form a similar monocationic complex, [NiII(S‐HLMe)(S‐H2LMe)]PF6 (S‐6PF6), which forms a dimer structure by double hydrogen bonds between the coordinating phenoxide and phenol groups in the crystal. Interestingly, the above complexes show slow racemization of the ligand, as confirmed by circular dichroism spectroscopy. Racemic NiII complexes of [Ni(HLMe)(H2LMe)](PF6 or Cl) (rac‐6PF6 or rac‐6Cl) are isolated and their crystal structures are confirmed by X‐ray diffraction analysis. In the case where Co(OAc)2 is used as the metal(II) salt, a new ligand dimerization reaction takes place to afford a complex of [Co(H2LLMe)]Cl (7Cl, H4LLMe = methyl (E)‐3‐{[3‐(1H‐imidazol‐4‐yl)‐1‐methoxy‐1‐oxopropano‐2‐yl]amino}‐2‐[(1H‐imidazol‐4‐yl)methyl]‐2‐[(2‐hydroxybenzylidene)amino]‐3‐(2‐hydroxyphenyl)propanoate).

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“…Oxo‐vanadium complexes have been extensively studied because of their potential applicability as catalysts or mediators for oxidations by molecular oxygen, peroxidative oxygenations (both including epoxidations), halogenations and carboxylations of aliphatic and aromatic hydrocarbons, and/or olefins, toward the syntheses of a variety of organic compounds, such as alcohols, ketones, epoxides, aldehydes, organohalides and carboxylic acids, and oxidation of organic sulfides to sulfoxides . Some of these systems operate in liquid media, whereas others involve VO catalysts immobilized on solid supports.…”

Section: Introductionmentioning

confidence: 99%

Immobilization of a vanadium complex onto functionalized nanoporous MCM‐41 and its application as a catalyst for the solvent‐free chemoselective oxidation of sulfide to sulfoxide

Nikoorazm

Ghorbani‐Choghamarani

Khanmoradi

2016

Applied Organom Chemis

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A complex moiety containing VO(IV) was anchored covalently into organic‐modified Si‐MCM‐41 to prepare a new catalyst. The prepared materials were characterized using various techniques. Several types of aromatic and aliphatic sulfides were successfully oxidized to the corresponding sulfoxides in good to excellent yields using H2O2 in the presence of a catalytic amount of the catalyst under solvent‐free conditions. The results showed that the OH groups of the various compounds such as 2,2‐(phenylthio)ethanol and 2‐(methylthio)ethanol remained intact under similar conditions. Meanwhile the catalyst was stable in the reaction system, and could be reused at least four times without significant loss of its activity and chemoselectivity. Copyright © 2016 John Wiley & Sons, Ltd.

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Synthesis, crystal structure and catalytic activity of a new Mo Schiff base complex with Mo histidine immobilized on Al-MCM-41 for oxidation of sulfides

Cited by 28 publications

References 48 publications

New magnetic supported hydrazone Schiff base dioxomolybdenum (VI) complex: An efficient nanocatalyst for epoxidation of cyclooctene and norbornene

New magnetic supported hydrazone Schiff base dioxomolybdenum (VI) complex: An efficient nanocatalyst for epoxidation of cyclooctene and norbornene

Schiff Base Ligands Derived from l‐Histidine Methyl Ester: Characterization, Racemization, and Dimerization of Their Transition‐Metal Complexes

Immobilization of a vanadium complex onto functionalized nanoporous MCM‐41 and its application as a catalyst for the solvent‐free chemoselective oxidation of sulfide to sulfoxide

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