Synthesis, Molecular Structure, and Solution-Dependent Behavior of Nickel Complexes Chelating Anilido−Imine Donors and Their Catalytic Activity toward Olefin Polymerization

Gao, Haiyang; Guo, Wen-Juan; Bao, Feng; Gui, Guoqiu; Zhang, Junkai; Zhu, Fangming; Wu, Qing

doi:10.1021/om049367t

Cited by 107 publications

(78 citation statements)

References 39 publications

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“…Similar to nickel complex of β-diketiminate ligands 23,35 and anilido-imine ligands, 36 two sets of proton signals, respectively, for monomer and dimer could be detected in the 1 H NMR spectra of complexes 1 and 2 in benzene-d 6 solution. The molar ratio of monomer to dimer could be calculated by hydrogen integration in the 1 H NMR spectra.…”

Section: 915(3)å and 9469(11)mentioning

confidence: 88%

“…2,6-Diisopropylaniline and 2,6-dimethylaniline were distilled from potassium hydroxide prior to use. Solid methylaluminoxane (MAO) 36 and (1,2-dimethoxyethane) nickel (II) bromide [(DME)NiBr 2 ] 57 were prepared according to literature procedures. n-Butyllithium in n-hexane solution (2.2 M) and 1,1,1,5,5,5-hexafluoroacetylacetone were purchased from Aldrich Chemical Co. Other commercially available reagents were used as received.…”

Section: Methodsmentioning

confidence: 99%

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Novel nickel (II) complexes chelating β‐diketiminate ligands: synthesis and simultaneous polymerization and oligomerization of ethylene

Wang

Gao

et al. 2006

Applied Organom Chemis

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Two novel nickel (II) complexes, CH{C(CF 3 )NAr} 2 NiBr (1, Ar = 2,6-i Pr 2 C 6 H 3 and 2, 2,6-Me 2 C 6 H 3 ), were synthesized by the reaction of the lithium salt of fluorinated β-diketiminate backbone ligands with (1,2-dimethoxyethane) nickel (II) bromide [(DME)NiBr 2 ]. The solid-state structure of nickel (II) complex 2 as a dimer reveals four-coordination and a tetrahedral geometry with bromide bridged by single crystal X-ray measurement. Both complexes catalyze simultaneous polymerization and oligomerization of ethylene when activated by methylaluminoxane (MAO). It was found that the reaction temperature has a pronounced effect on the activity of ethylene polymerization and the molecular weight of obtained polyethylene. In addition, the nickel catalytic systems predominantly produce linear polyethylene with unsaturated end groups.

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Section: 915(3)å and 9469(11)mentioning

confidence: 88%

Section: Methodsmentioning

confidence: 99%

Novel nickel (II) complexes chelating β‐diketiminate ligands: synthesis and simultaneous polymerization and oligomerization of ethylene

Wang

Gao

et al. 2006

Applied Organom Chemis

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“…Similarly, zinc complexes with the anilido-imine ligands might also be efficient luminescent 4168 elimination. All compounds were characterized by elemental analysis and 1 H and 13 C NMR spectroscopy. The molecular structures of compounds 2a, 2b, 3b, and 3c were determined by single-crystal X-ray crystallography.…”

Section: Introductionmentioning

confidence: 99%

Syntheses, Characterization, and Luminescent Properties of Monoethylzinc Complexes with Anilido–Imine Ligands

Gao

et al. 2007

Eur J Inorg Chem

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The syntheses of three anilido–imine ligands of the general formula ortho‐C6H4(NHAr′)(CH=NAr″ [Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″ = 2,6‐Me2C6H3 (2a); Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″= 2,6‐Et2C6H3 (2b); Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″= 2,6‐iPr2C6H3 (2c)] and four zinc(II) complexes of the general formula [ortho‐C6H4(NHAr′)(CH=NAr″)]ZnEt [Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″= 2,6‐Me2C6H3 (3a); Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″= 2,6‐Et2C6H3 (3b); Ar′ = 7‐(2,4‐Me2)C9H4N, Ar″ = 2,6‐iPr2C6H3 (3c); Ar″ = 2,6‐Me2C6H3, Ar″ = 2,6‐iPr2C6H3 (3d)] are described. The complexes were synthesized from the reaction of ZnEt2 with corresponding ligands 2 by alkane elimination. All compounds were characterized by elemental analysis and 1H and 13C NMR spectroscopy. The molecular structures of compounds 2a, 2b, 3b, and 3c were determined by single‐crystal X‐ray crystallography. The X‐ray analysis reveals that complexes 3b and 3c exist in the dimeric form with the N atom in the quinolyl ring coordinating to the other Zn atom to make the Zn atoms four coordinate. Luminescent properties of ligands 2a–2d and complexes 3a–3d in both solution and the solid state were studied. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…The properties and molecular structure of complexes containing the amine group are of interest as their complexes with transition metal exhibit superior activity as catalysts in polymerizations [1,2]. The asymmetric unit of the title compound is built up from two independent but similar molecules.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N-(benzo[d][1,3]dioxol-5-ylmethyl)- 4-methylaniline, C15H13NO2

Yin¹,

Fei²,

Qian³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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C 15 H 13 NO 2 ,triclinic, P1 (no. 2), a =10.697(3) Å, b =10.791(3) Å, c =13.328(3) Å, a =89.39(2)°, b =67.05(2)°, g =62.45(3)°, V =1228.6 Å 3 , Z =4, Source of material]dioxole-5-carbaldehyde (2 mmol, 0.30 g) was dissolved in anhydrous methanol (10 ml), the mixture was stirred for several minitutes at room temperature, p-toluidine (2 mmol, 0.214 g) in methanol (5 ml) was added dropwise and the mixture was stirred at room temperature for 2h.The Schiff base was obtained and reduced with sodium borohydride (5 mmol, 0.185 g), The mixture was stirred for 5hatRT, then evaporated to dryness, the product was recrystallised from methanol, colorless single crystals of the title compound were obtained after 1d. DiscussionThe properties and molecular structure of complexes containing the amine group are of interest as their complexes with transition metal exhibit superior activity as catalysts in polymerizations [1,2]. The asymmetric unit of the title compound is built up from two independent but similar molecules. The title molecule crystallizes in the E conformation in each molecule, with the C9-N1-C8-C1and C24-N2-C23-C16 torsion angles of 172.6(2) and -178.9(2)°,1 ,3-dioxolane ring is almost co-planar with its attached benzene ring [dihedral angle =1 .3(1)°and 3.2(2)°], respectively. Each molecule is not planar, the dihedral angles between the two benzene ring are 42.4(1)°and 19.7(1)°in each molecule, respectively. The N1-C8 and N2-C23 bond distances of 1.273(2) and 1.271(2) Å are typical for the C=N double bond. Classic hydrogen bonds were not observed in the molecule.

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Synthesis, Molecular Structure, and Solution-Dependent Behavior of Nickel Complexes Chelating Anilido−Imine Donors and Their Catalytic Activity toward Olefin Polymerization

Cited by 107 publications

References 39 publications

Novel nickel (II) complexes chelating β‐diketiminate ligands: synthesis and simultaneous polymerization and oligomerization of ethylene

Novel nickel (II) complexes chelating β‐diketiminate ligands: synthesis and simultaneous polymerization and oligomerization of ethylene

Syntheses, Characterization, and Luminescent Properties of Monoethylzinc Complexes with Anilido–Imine Ligands

Crystal structure of N-(benzo[d][1,3]dioxol-5-ylmethyl)- 4-methylaniline, C15H13NO2

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