Palladium complexes bearing κ2-N,N and κ3-N,N,O pendant amine bis(phenolate) ligands

Graziano, Brendan J.; Collins, Eric M.; McCutcheon, Nathaniel C.; Griffith, Claire L.; Braunscheidel, Nicole M.; Perrine, Trilisa M.; Wile, Bradley M.

doi:10.1016/j.ica.2018.09.032

Cited by 9 publications

(10 citation statements)

References 73 publications

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“…Both metal centers adopt similar distorted square-planar geometric arrangements, in which both nitrogen atoms of the ligand are bound to the Pd center to form a five-membered ring, and either one or two chlorine atoms are present to complete the coordination sphere depending on the coordination mode of the ligand. In both complexes, the N-Pd-N bond angle is similar to those observed for related amine bis(phenolate) Pd complexes (Graziano et al, 2019), as described in Table 1.…”

Section: Structural Commentarysupporting

confidence: 75%

“…(Williams et al, 2003;Labourdette et al, 2009) Related modification to the amine bis(phenolate) framework generated 'claw-type' 3 Zn (Song et al, 2012;Wang et al, 2010) and Ti (Zhao et al, 2014) complexes that serve as competent polymerization catalysts. To our knowledge, only one report describes Pd complexes with amine bis(phenolate) ligands bound in a 2 or 3 coordination mode, in which both amine donors remain bound, and one phenolate donor may bind to the Pd center (Graziano et al, 2019). These species exhibit coordination behavior that varies with the steric parameters of the phenolate ortho and para substituents, with larger cumyl substituents favoring the formation of 2 complexes.…”

Section: Chemical Contextmentioning

confidence: 99%

“…Both species within this unit cell are generated upon combining equimolar quantities (0.254 mmol) of the {6,6 0 -[(ethane-1,2-diylbis(methylazanediyl)]bis(methylene)}bis(2,4di-tert-butylphenol) ligand and bis(benzonitrile)dichloropalladium(II) in 5 mL of acetonitrile, using the method reported previously by Wile and co-workers (Graziano et al, 2019) as shown in Fig. 3.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

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Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ² and κ³ coordination modes

Graziano

Wile

Zeller

2019

Acta Crystallogr E Cryst Commun

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Bidentate and tridentate coordination of a 2,4-di-tert-butyl-substituted bridging amine bis(phenolate) ligand to a palladium(II) center are observed within the same crystal structure, namely dichlorido({6,6′-[(ethane-1,2-diylbis(methylazanediyl)]bis(methylene)}bis(2,4-di-tert-butylphenol))palladium(II) chlorido(2,4-di-tert-butyl-6-{[(2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methyl](methyl)amino}ethyl)(methyl)amino]methyl}phenolato)palladium(II) methanol 1.685-solvate 0.315-hydrate, [PdCl2(C34H56N2O2)][PdCl(C34H55N2O2)]·1.685CH3OH·0.315H2O. Both complexes exhibit a square-planar geometry, with unbound phenol moieties participating in intermolecular hydrogen bonding with co-crystallized water and methanol. The presence of both κ2 and κ3 coordination modes arising from the same solution suggest a dynamic process in which phenol donors may coordinate or dissociate from the metal center, and offers insight into catalyst speciation throughout Pd-mediated processes. The unit cell contains dichlorido({6,6′-[(ethane-1,2-diylbis(methylazanediyl)]bis(methylene)}bis(2,4-di-tert-butylphenol))palladium(II), {(L 2)PdCl2}, and chlorido(2,4-di-tert-butyl-6-{[(2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methyl](methyl)amino}ethyl)(methyl)amino]methyl}phenolato)palladium(II), {(L 2 X)PdCl}, molecules as well as fractional water and methanol solvent molecules.

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Section: Structural Commentarysupporting

confidence: 75%

Section: Chemical Contextmentioning

confidence: 99%

Section: Synthesis and Crystallizationmentioning

confidence: 99%

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Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ² and κ³ coordination modes

Graziano

Wile

Zeller

2019

Acta Crystallogr E Cryst Commun

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“…The bond lengths between palladium and nitrogen, oxygen and chlorine atoms were found to be N19−Pd33 = 1.952Å, O29−Pd33 = 1.922Å, and Pd33−Cl34 = 2.27Å. They were in the normal range for these bonds as observed before [39,40]. For example, the palladium complex [PdCl 2 (L)], L = 2,6-diisopropyl-N-[(S)-pyrrolidin-2ylmethyl]-aniline, exhibited Pd-N bond lengths equal to 2.04Å and 2.07Å, and Pd-Cl bond lengths equal to 2.31Å and 2.32Å [39].…”

Section: The Stereochemistry and Chemical Reactivity Predictionsupporting

confidence: 67%

Spectroscopic and Theoretical Studies of Some Bivalent Metal Complexes of a Quinoline Schiff Base Derivative

Ramadan¹,

Mohamed²,

Hassan³

et al. 2020

J Trans Met Compl

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Interaction of M(II) ions, M− −Co, Ni, Cu, Zn, and Pd, with a Schiff base ligand (HL), derived from the condensation of 2-hydroxy-5-nitrobenzaldehyde and 8-aminoquinoline, gave the complexes COO, and [Pd(HL)Cl 2 ]. The ligand and its complexes were characterized by means of elemental and thermal analyses, molar conductance, and magnetic moment measurements along with the different spectroscopic techniques. Theoretical calculations based on DFT were carried out to verify the optimized structures of ligand and complexes. The relative reactivity of the compounds was estimated from chemical descriptors analysis using the HOMO and LUMO frontier orbitals. Molecular docking of ligand and its zinc complex revealed that the interaction of Zn(L) with DNA is comparable to that of HL due to the presence of water OH groups instead of the hydroxyl group of ligand.

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“…The ligand H 2 ONNO F (1) was prepared by the method reported previously (Graziano et al, 2019). The Mo complex (2) was prepared using a modified version of the method reported by Lehtonen & Sillanpä ä (2005).…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Dioxidomolybdenum(VI) complex featuring a 2,4-difluoro-substituted amine bis(phenolate) ligand

Bowen

Wile

2021

IUCr Data

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Synthetic complexes containing a cis-[MoO2]2+ core are well-established models for the molybdenum co-factor (Moco). Here we report the crystal structure of such a model complex bearing a tetradentate amine bis(phenolate) ligand with fluorine substituents on the phenolate rings, namely, [2,2′-({[2-(dimethylamino)ethyl]azanediyl}bis(methylene))bis(4,6-difluorophenolato)]dioxoidomolybdenum(VI)), [Mo(C18H18F4N2O2)O2]. Distortion from idealized octahedral symmetry about the Mo center is evident in the large O=Mo=O angle [108.54 (4)°] and the small N–Mo–Ophenolate angles [79.79 (4), 81.21 (3), 77.83 (3), and 84.59 (3)°]. The dihedral angle between the phenolate rings is 60.06 (4)°, and π–π stacking is observed between aromatic rings related by inversion (1 − x, 1 − y, 1 − z). The lower data-collection temperature of 150 K vs room-temperature data collection reported previously [KOWXIF; Cao et al. (2014). Transit. Met. Chem. 39, 933–937] and larger 2θ range for data collection (5.8–66.6° versus 6–54.96°) led to a structure with lower R 1 and ωR 2 values (0.019 and 0.049 vs 0.0310 and 0.0566 for KOWXIF). Comparison of the metrical parameters with KOWXIF suggests that this dataset offers a more realistic depiction of bonding within the MoVI=O moiety.

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Palladium complexes bearing κ2-N,N and κ3-N,N,O pendant amine bis(phenolate) ligands

Cited by 9 publications

References 73 publications

Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ² and κ³ coordination modes

Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ² and κ³ coordination modes

Spectroscopic and Theoretical Studies of Some Bivalent Metal Complexes of a Quinoline Schiff Base Derivative

Dioxidomolybdenum(VI) complex featuring a 2,4-difluoro-substituted amine bis(phenolate) ligand

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Palladium complexes bearing κ2-N,N and κ3-N,N,O pendant amine bis(phenolate) ligands

Cited by 9 publications

References 73 publications

Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ2 and κ3 coordination modes

Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ2 and κ3 coordination modes

Spectroscopic and Theoretical Studies of Some Bivalent Metal Complexes of a Quinoline Schiff Base Derivative

Dioxidomolybdenum(VI) complex featuring a 2,4-difluoro-substituted amine bis(phenolate) ligand

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Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ² and κ³ coordination modes

Palladium(II) complexes of a bridging amine bis(phenolate) ligand featuring κ² and κ³ coordination modes