The Adaptable Coordination Chemistry of 6‐Chloro‐2‐(quinolin‐2‐yl)‐2,4‐dihydro‐1<i>H</i>‐benzo[<i>d</i>][1,3]oxazine Towards Zinc(II) and Mercury(II)

Ardizzoia, G. Attilio; Brenna, Stefano; Therrien, Bruno

doi:10.1002/ejic.201000175

Cited by 17 publications

(10 citation statements)

References 23 publications

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“…As expected, the geometry around each metal center is tetrahedral, and the bond lengths and angles for each zinc atom are comparable to those found in previously described complexes with an analogous Zn(N∩N)Cl 2 18c or Zn(N∩N)I 2 28 environment. The dihedral angles show a nearly planar configuration for the pyridylimidazo[1,5‐ a ]pyridine moiety of the ligand: the N(1)–C(5)–C(6)–N(3) and C(4)–C(5)–C(6)–C(7) angles are –4.6(5) and –5.7(7)° in [Zn(L Me )Cl 2 ], –5.4(4) and –9.2(6)° in [Zn(L Me )I 2 ], and –1.5(4) and –0.8(5)° in [Zn(L OH )Cl 2 ].…”

Section: Resultssupporting

confidence: 87%

Synthesis, Structure, and Photophysical Properties of Blue‐Emitting Zinc(II) Complexes with 3‐Aryl‐Substituted 1‐Pyridylimidazo[1,5‐a]pyridine Ligands

et al. 2014

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Six zinc(II) complexes of the general formula [Zn(LR)X2] (1: R = Me, X = Cl; 2: R = Me, X = Br; 3: R = Me, X = I; 4: R = OH, X = Cl; 5: R = OH, X = Br; 6: R = OH, X = I), in which LR is 1‐(pyridin‐2‐yl)‐3‐o‐tolylimidazo[1,5‐a]pyridine (LMe) or 2‐[1‐(pyridin‐2‐yl)imidazo[1,5‐a]pyridin‐3‐yl]phenol (LOH), have been prepared and characterized. The X‐ray structural analysis performed on complexes 1, 3, and 4 showed that both LMe and LOH act as N,N‐bidentate ligands and coordinate to the ZnII metal center through the pyridine ring (Npy) and the pyridine‐like nitrogen atom of the imidazo[1,5‐a]pyridine group (Nim). The photophysical properties of these compounds have been investigated, both in solution and in the solid state. The complexes showed intense blue luminescence when excited with UV light (λexc = 366–410 nm) with λmax of emission between 440–460 nm in the solid state. Complexes 1–3 showed moderate‐to‐good absolute photoluminescence quantum yields (PLQYs) in the solid state with a maximum PLQY of 0.40 for 1. These values were slightly lower than the PLQY of free LMe (0.60). On the other hand, the PLQY of LOH increased after coordination to ZnCl2, and a PLQY of 0.29 was recorded for 4. A possible interpretation of this behavior is reported.

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Section: Resultssupporting

confidence: 87%

Synthesis, Structure, and Photophysical Properties of Blue‐Emitting Zinc(II) Complexes with 3‐Aryl‐Substituted 1‐Pyridylimidazo[1,5‐a]pyridine Ligands

et al. 2014

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“…The Co(II) ion has a tetrahedral environmentby the coordination of two nitrogen atoms of a bidentate ligand and two chloride anions. The geometrical parameters around the central metal atom are comparable to those found in an analogous complex, [Zn( 6 The distortions in the coordination spheres were predicted by the τ4 value, calculated from the equation τ4 = {360 -(α + β)}/141, where α and β are the largest and second-largest L-Co-L angles, respectively. 7 τ4 is 1 and 0 for perfect tetrahedral and square planar geometries.…”

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confidence: 53%

Crystal Structure of Dichloro{2-(quinolin-2-yl)-4H-benzo[d][1,3]oxazine}cobalt(II)

KANEGAE

Yoneda

Koikawa

2022

X-ray Structure Analysis Online

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The title compound, [CoCl2(qboz)], [qboz = 2-(quinolin-2-yl)-4H-benzo [d][1,3]oxazine], was synthesized and characterized by single-crystal X-ray analysis. This compound crystallizes in the triclinic space group P1 with cell parameters of a = 7.996(5)Å, b = 8.580(6)Å, c = 12.508(8)Å, α = 99.154(11)°, β = 93.012(11)°, γ = 108.108(8)°, V = 800.5(9)Å 3 , Dcalcd = 1.618 g/cm 3 , Z = 2. The R1 [I > 2σ(I)] and wR2 (all data) values are 0.0345 and 0.0875, respectively, for all 3549 independent reflections. The benzoxazine ligand is believed to have been obtained by the nucleophilic addition of benzyl alcohol to imine carbon and the subsequent metal-catalyzed air oxidation of the Schiff-base ligand.

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“…To the best of our knowledge, this represents the sole example reported in the literature of a crystallographic investigation of a nickel-oxazolidine complex. Despite analogous systems previously described by us 12,13 showing the N,N¢ coordination towards hard ions such as Zn 2+ and Cu 2+ (absolute hardness (eV): Zn 2+ : 10.8; Cu 2+ : 8.3, respectively), in the case of ppo the N,N¢ coordination is encountered for the soft Pd 2+ (6.8 eV), the hard Ni 2+ centre (8.5 eV) inducing N,O coordination to ppo. This apparently conflicting conduct has presumably to be ascribed to the intrinsic electronic features of the oxazolidine and the oxazine ligands.…”

Section: Synthesis and Characterisation Of The Complexesmentioning

confidence: 69%

“…The configuration at the metal centre is determined by the X-ray structure analysis of [Ni(ppo) 2 Cl 2 ]. The crystals are obtained 4), Cl1-Pd1-N2 94.41 (10), Cl2-Pd1-N1 93.40 (10), N1-Pd1-N2 82.23 (13).…”

Section: Synthesis and Characterisation Of The Complexesmentioning

confidence: 99%

“…We recently initiated a study on the coordination chemistry of fully saturated N-containing heterocylces and we have already reported on the coordination chemistry of dihydrobenzoxazinetype ligands towards copper 12 and group-12 metals. 13 To continue this study, we have now tested the coordination chemistry of ligands based on five-membered rings, specifically those containing an oxazolidine skeleton. Herein we report the coordination chemistry of 3-phenyl-2-(pyridin-2-yl)oxazolidine (ppo) towards Pd(II) and Ni(II) centres.…”

Section: Introductionmentioning

confidence: 99%

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Ni(ii) and Pd(ii) pyridinyloxazolidine-compounds: synthesis, X-ray characterisation and catalytic activities in the aza-Michael reaction

2012

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The 3-phenyl-2-(pyridin-2-yl)oxazolidine ligand (ppo) was synthesised and its coordination behaviour regarding Ni(II) and Pd(II) centres was studied. The reaction with K(2)PdCl(4) affords [Pd(N,N'-ppo)Cl(2)] (1), in which ppo binds to palladium via the pyridyl nitrogen and the oxazolyl nitrogen atoms. On the contrary, reaction with NiCl(2)·6H(2)O produces [Ni(N,O-ppo)(2)Cl(2)] (2), in which two ppo ligands are coordinated via the pyridyl nitrogen and the oxygen atom of the oxazolidine ring. The X-ray diffraction analysis of the complexes confirms a square planar geometry for Pd(II) in 1 and an octahedral configuration around Ni(II) in 2, which, to the best of our knowledge, represents the first reported example of a structurally characterised nickel-oxazolidine compound. In addition, both complexes prove to be active catalysts under mild conditions in the aza-Michael reaction of (E)-4-phenylbut-3-en-2-one (benzalacetone) with aliphatic amines.

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The Adaptable Coordination Chemistry of 6‐Chloro‐2‐(quinolin‐2‐yl)‐2,4‐dihydro‐1H‐benzo[d][1,3]oxazine Towards Zinc(II) and Mercury(II)

Cited by 17 publications

References 23 publications

Synthesis, Structure, and Photophysical Properties of Blue‐Emitting Zinc(II) Complexes with 3‐Aryl‐Substituted 1‐Pyridylimidazo[1,5‐a]pyridine Ligands

Synthesis, Structure, and Photophysical Properties of Blue‐Emitting Zinc(II) Complexes with 3‐Aryl‐Substituted 1‐Pyridylimidazo[1,5‐a]pyridine Ligands

Crystal Structure of Dichloro{2-(quinolin-2-yl)-4H-benzo[d][1,3]oxazine}cobalt(II)

Ni(ii) and Pd(ii) pyridinyloxazolidine-compounds: synthesis, X-ray characterisation and catalytic activities in the aza-Michael reaction

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