Evaluating the electronic properties of ditopic and hetero-ditopic ligands derived from benzimidazole and pyrazole by 13C NMR spectroscopy

Teng, Qiaoqiao; Lu, Yung-Hsiu; Zhu, Rui; Huynh, Han Vinh; Meng, Qing

doi:10.1016/j.jorganchem.2020.121409

Cited by 3 publications

(2 citation statements)

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“…The square‐base pyramid geometry of the metal center comprises two nitrogen and two halogen atoms (in cis positions) located in the basal plane while a hydrogen atom occupies the apical position. In general, the Pd−N pyrazole , Pd−Cl and Pd‐Br bond distances are in agreement with analogue palladium compounds reported in the literature [5,7,30–38] . The six membered chelate metallacycle formed due to the coordination of two nitrogen atoms of pyrazole rings towards the Pd(II) metal center adopts a boat conformation.…”

Section: Resultssupporting

confidence: 88%

“…The square-base pyramid geometry of the metal center comprises two nitrogen and two halogen atoms (in cis positions) located In general, the PdÀ N pyrazole , PdÀ Cl and Pd-Br bond distances are in agreement with analogue palladium compounds reported in the literature. [5,7,[30][31][32][33][34][35][36][37][38] The six membered chelate metallacycle formed due to the coordination of two nitrogen atoms of pyrazole rings towards the Pd(II) metal center adopts a boat conformation. The Pd•••H δ À C( Those values are similar to those found in another ionic and neutral compounds CSD structures = BUJLUO, SEJVOV, MOVLIS and ULOTOE respectively.…”

Section: Synthesis Of Complexes 2 Andmentioning

confidence: 99%

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Coordination from Heteroscorpionate Ligand Towards Pd(II) via Pd⋅⋅⋅Hδ−C(sp3) Interaction: Structural and Catalytic Studies

et al. 2021

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The coordination ability of the heteroscorpionate ligand 2,2-bis (3,5-dimethylpyrazol-1-yl)-1-p-tolylethanol (1) towards palladium (II) dihalides was evaluated. The structures of the respective palladium complexes (2 and 3) were elucidated in solution by NMR spectroscopy, and their molecular structures were established by single crystal X-ray diffraction analyses. Both studies revealed the existence of Pd•••H δ À C(sp 3 ) anagostic interactions. The molecular structure of complexes 2 and 3 displays coordination of ligand 1 to palladium in a k 3 -NNH tridentate fashion via two nitrogen atoms and one δ-anagostic H•••Pd interaction. The metal center exhibits a square pyramidal geometry. The distances of anagostic H δ •••Pd interactions ranged from 2.566 to 2.576 Å. The δ-anagostic H•••Pd interactions in complexes 2 and 3 were also identified by Bader's quantum theory of atoms in molecules (QTAIM) and non-covalent interaction (NCI) analysis. The catalytic efficiencies of complexes 2 and 3 in the Suzuki-Miyaura cross-coupling reactions were evaluated and the results showed that palladium (II) dibromide complex is the most efficient of the series. Complex 3 was also evaluated in Mizoroki-Heck cross-coupling reactions.

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Section: Resultssupporting

confidence: 88%

Section: Synthesis Of Complexes 2 Andmentioning

confidence: 99%

Coordination from Heteroscorpionate Ligand Towards Pd(II) via Pd⋅⋅⋅Hδ−C(sp3) Interaction: Structural and Catalytic Studies

et al. 2021

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Tetra- and Dinuclear Palladium Complexes Based on a Ligand of 2,8-Di-2-pyridinylanthyridine: Preparation, Characterization, and Catalytic Activity

Lin

Liu

et al. 2021

Organometallics

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Complexation of L [L = 5-phenyl-2,8-di-2-pyridinyl-anthyridine] with [Pd(CH 3 CN) 4 ](BF 4 ) 2 and [Pd(CH 3 CN) 3 Cl](BF 4 ) in a molar ratio of 1:2 rendered the corresponding dinuclear complexes [Pd 2 L (CH 3 CN) 4 ](BF 4 ) 4 (1) and [Pd 2 L (CH 3 CN) 2 Cl 2 ](BF 4 ) 2 ( 2), respectively. However, treatment of L with (COD)PdCl 2 followed by anion exchange yielded a tetranuclear complex [Pd 4 L 3 Cl 4 ](PF 6 ) 4 (4a). Structures of these complexes are characterized by both spectroscopy and X-ray crystallography. Interconversion of these three complexes was studied via the manipulation of stoichiometric ratio of ligand to metal precursor. The catalytic activity of these complexes for carbonylative Suzuki− Miyaura cross-coupling was investigated. Complex 2 shows an excellent catalytic activity on the reaction of aryl iodide with arylboronic acid in the presence of atmospheric pressure of CO to give the corresponding benzophenones.

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Recent Applications of the Huynh Electronic Parameter (HEP)

Huynh

2021

Chemistry Letters

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The Huynh electronic parameter (HEP) is a modern alternative method to determine ligand donor strengths by 13C NMR spectroscopy of metal NHC complexes containing the ligand of interest. Using the HEP, the electronic properties of numerous classical Werner-type and organometallic ligands have been evaluated thus far. Moreover, it has been extended to the HEP2, which provides a means to measure bidentate chelators. This Highlight Review covers recent applications of the HEP and its variants from 2016 onwards.

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Evaluating the electronic properties of ditopic and hetero-ditopic ligands derived from benzimidazole and pyrazole by 13C NMR spectroscopy

Cited by 3 publications

References 59 publications

Coordination from Heteroscorpionate Ligand Towards Pd(II) via Pd⋅⋅⋅Hδ−C(sp3) Interaction: Structural and Catalytic Studies

Coordination from Heteroscorpionate Ligand Towards Pd(II) via Pd⋅⋅⋅Hδ−C(sp3) Interaction: Structural and Catalytic Studies

Tetra- and Dinuclear Palladium Complexes Based on a Ligand of 2,8-Di-2-pyridinylanthyridine: Preparation, Characterization, and Catalytic Activity

Recent Applications of the Huynh Electronic Parameter (HEP)

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