Gold(<scp>i</scp>) complexes with heteroaryl phosphine ligands

Sarcher, Christian; Farsadpour, Saeid; Ghoochany, Leila Taghizadeh; Sun, Yu; Thiel, Werner R.; Roesky, Peter W.

doi:10.1039/c3dt52893f

Cited by 12 publications

(10 citation statements)

References 57 publications

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“…The pyrimidine group, containing both proton-donating and proton-accepting sites, enables dimerization by formation of hydrogen bonds in the solid state, achieving N-HÁ Á ÁN hydrogen-bond distances that are in the typical range of hydrogen bonds between aminopyrimidines. The values of the resulting electrostatic potentials in this molecular system make it possible to predict the formation of additional hydrogen bonds or the possible formation of covalent bonds in a synthesis process (Sarcher et al, 2014). Nucleophilic substitution reactions performed in our research group followed an effective path involving the amino functional group and resulted in the formation of new covalent bonds by integrating different heterocyclic rings into the reaction products.…”

Section: Molecular Electrostatic Potential (Mep)mentioning

confidence: 99%

Synthesis, spectroscopic (FT–IR and UV–Vis), crystallographic and theoretical studies, and a molecular docking simulation of an imatinib-like template

et al. 2019

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The aim of the present study was to report the crystal structure and spectroscopic, electronic, supramolecular and electrostatic properties of a new polymorph of 4-(pyridin-2-yl)pyrimidin-2-amine (C 9 H 8 N 4 ). The compound was synthesized under microwave irradiation. The single-crystal X-ray structure analysis revealed an angle of 13.36 (8) between the planes of the rings, as well as molecules linked by Nsp 2 -HÁ Á ÁN hydrogen bonds forming dimers along the crystal. The material was analyzed by FT-IR vibrational spectroscopy, while a computational approach was used to elucidate the vibrational frequency couplings. The existence of Nsp 2 -HÁ Á ÁN hydrogen bonds in the crystal was confirmed spectroscopically by the IR peaks from the N-H stretching vibration shifting to lower wavenumbers in the solid state relative to those in the gas phase. The supramolecular studies confirmed the formation of centrosymmetric R 2 2 (8) rings, which correspond to the formation of dimers that stack parallel to the b direction. Other weak C-HÁ Á Á interactions, essential for crystal growth, were found. The UV-Vis spectroscopic analysis showed a donor-acceptor process, where the amino group acts as a donor and the pyridine and pyrimidine rings act as acceptors. The reactive sites of the molecule were identified and their quantitative values were defined using the electrostatic potential model proposed in the multifunctional wave function analyzer multiwfn. The calculated interaction energies between pairs of molecules were used to visualize the electrostatic terms as the leading factors against the dispersion factors in the crystal-growth process. The docking results showed that the amino group of the pyrimidine moiety was simultaneously anchored by hydrogen-bonding interactions with the Asp427 and His407 protein residues. This compound could be key for the realization of a series of syntheses of molecules that could be used as possible inhibitors of chronic myelogenous leukemia. research papers 1682 Moreno-Fuquen et al. Analysis of an imatinib-like template

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Section: Molecular Electrostatic Potential (Mep)mentioning

confidence: 99%

Synthesis, spectroscopic (FT–IR and UV–Vis), crystallographic and theoretical studies, and a molecular docking simulation of an imatinib-like template

et al. 2019

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“…The N–H···N bond distances (H3···N5 2.174 Å and H6···N2 2.077 Å) are in the typical range of hydrogen bonds. 69 The N2···N6 and N3···N5 distances are 2.952 and 3.037 Å, whereas the N2···H6–N6 and N5···H3–N3 angles are 172.74 and 166.18°, respectively.…”

Section: Resultsmentioning

confidence: 95%

Diverse Architectures and Luminescence Properties of Group 11 Complexes Containing Pyrimidine-Based Phosphine, N-((Diphenylphosphine)methyl)pyrimidin-2-amine

2018

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In this article, the synthesis, structural studies, and luminescence properties of Cu I , Ag I , and Au I complexes of pyrimidine-based phosphine [C 4 H 3 N 2 -2-NH(CH 2 PPh 2 )] ( 1 ) are described. The reactions of 1 with CuX led to the isolation of one-dimensional (1D) chain, tetranuclear ladder, or cyclic derivatives. The structural features of these complexes are greatly influenced by the metal-to-ligand ratio, reaction conditions, and CuX (X = Cl, Br or I) employed. In the case of CuCl and CuBr, one-dimensional coordination polymers [{CuCl}{C 4 H 3 N 2 -2-NH(CH 2 PPh 2 )}] ∞ ( 2 ) and [{CuBr}{C 4 H 3 N 2 -2-NH(CH 2 PPh 2 )}] ∞ ( 3 ) were obtained, whereas CuI afforded tetracopper complex [{CuI} 4 {C 4 H 3 N 2 -2-NH(CH 2 PPh 2 )} 2 (NCCH 3 ) 2 ] ( 4 ) having Cu 4 ladder structure supported by P∩N-bridging coordination of 1 . The reaction of 1 with AgOTf yielded unprecedented one-dimensional chain structure [{AgOTf}{C 4 H 3 N 2 -2-NH(CH 2 PPh 2 )}] ∞ ( 5 ), whereas the reaction with AgBF 4 produced a 12-membered dinuclear complex, [{Ag}{C 4 H 3 N 2 -2-NH(CH 2 PPh 2 )}] 2 [BF 4 ] 2 ( 6 ), with each silver atom having a linear geometry. Gold complex [{AuCl}{C 4 H 3 N 2 -2-NH(CH 2 PPh 2 )}] 2 ( 7 ) was synthesized by reacting 1 with [AuCl(SMe 2 )]. Compounds 2 – 4 were also prepared using a pestle and mortar by grinding method in almost quantitative yield. Complex 4 with a Cu···Cu distance of 2.828(5) Å shows high luminescence due to the nonbonded metal···metal interactions.

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“…Ligand L11 was synthesised from 2‐(2‐aminopyrimidin‐4‐yl)pyridine by reaction with Ph 2 PCl in the presence of a base . The benzimidazolyl phosphine ligand L12 was synthesised through a sequence of cyclisation, alkylation and phosphonation reactions starting from 2‐bromobenzoic acid and 1,2‐phenylenediamine .…”

Section: Resultsmentioning

confidence: 99%

“…The precursors 9 a , b and the ligands L1 , L2 , L7 , L8 and L9 as well as L10 , L11 and L12 were synthesised according to procedures published in the literature. The analytical data matched those reported in the literature.…”

Section: Methodsmentioning

confidence: 99%

Bimetallic Cu/Pd Catalysts with Bridging Aminopyrimidinyl Phosphines for Decarboxylative Cross‐Coupling Reactions at Moderate Temperature

et al. 2015

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A bimetallic catalyst system is presented that enables the decarboxylative cross‐coupling of triflates with carboxylate salts at only 100 °C, which is 70 °C lower than with previous Cu/Pd‐based systems. The new protocol allows the coupling of a broad range of aryl triflates with various substituted 2‐nitrobenzoates in good to excellent yields. The key feature of the catalyst system is a bidentate P,N‐ligand designed to bridge the Pd and Cu centres and thereby facilitating the rate‐determining transmetalation step. Mass spectrometry (ESI‐MS) studies support the ability of the aminopyrimidinyl phosphine to simultaneously coordinate copper and palladium.

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Gold(i) complexes with heteroaryl phosphine ligands

Cited by 12 publications

References 57 publications

Synthesis, spectroscopic (FT–IR and UV–Vis), crystallographic and theoretical studies, and a molecular docking simulation of an imatinib-like template

Synthesis, spectroscopic (FT–IR and UV–Vis), crystallographic and theoretical studies, and a molecular docking simulation of an imatinib-like template

Diverse Architectures and Luminescence Properties of Group 11 Complexes Containing Pyrimidine-Based Phosphine, N-((Diphenylphosphine)methyl)pyrimidin-2-amine

Bimetallic Cu/Pd Catalysts with Bridging Aminopyrimidinyl Phosphines for Decarboxylative Cross‐Coupling Reactions at Moderate Temperature

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