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Keywords = tris(pyrazolyl)methane

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8 pages, 2707 KB  
Communication
4-(Tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline
by Bradley B. Garrison, Joseph E. Duhamel, Nehemiah Antoine, Steven J. K. Symes, Kyle A. Grice, Colin D. McMillen and Jared A. Pienkos
Molbank 2024, 2024(2), M1823; https://doi.org/10.3390/M1823 - 17 May 2024
Viewed by 3318
Abstract
4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and single-crystal [...] Read more.
4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and single-crystal analysis. An analysis of crystals grown from the layering method (CH2Cl2/acetone/pentane) indicated two distinct polymorphs of the title compound. Moreover, density functional theory calculations utilizing the MN15L density functional and the def2-TZVP basis set indicated that 4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline forms with similar energetics to the previously reported unmethylated analog. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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15 pages, 2064 KB  
Article
The Synthesis, Crystal Structure, and Magnetic Properties of Mono-Scorpionate Eu(III) Complexes
by Kira E. Vostrikova, Taisiya S. Sukhikh and Alexander N. Lavrov
Inorganics 2023, 11(10), 418; https://doi.org/10.3390/inorganics11100418 - 23 Oct 2023
Cited by 7 | Viewed by 2471
Abstract
Three Eu3+ complexes containing a neutral tripodal ligand possessing a predictable coordination mode have been obtained and studied. The trispyrazolylmethane complexes have an aqua ligand in the coordination sphere, forming both the mononuclear species [Eu(HCPz3)H2O(NO3)3 [...] Read more.
Three Eu3+ complexes containing a neutral tripodal ligand possessing a predictable coordination mode have been obtained and studied. The trispyrazolylmethane complexes have an aqua ligand in the coordination sphere, forming both the mononuclear species [Eu(HCPz3)H2O(NO3)3] and the dimer [Eu(HCPz3)H2O(CF3SO3)3]2, having a Chinese lantern structure, whereas the use of the methylated tripod leads to the water-free complex, [Eu(HC(PzMe2)3)(NO3)3]. A qualitative analysis of the magnetic susceptibility of polycrystalline samples demonstrated that the magnetic properties can be described using a simple Van Vleck formula with spin–orbit coupling parameter (λ = 383 ÷ 406 cm−1) close to the values for free Eu3+ ions. The stereochemical analysis of the coordination environment of [Ln(HC(PzMe2)3)(NO3)3] has shown that these complexes can be used as diamagnetic model systems to obtain information on the crystal field effects in the paramagnetic monoradical complexes, [LnRad(NO3)3], since both types of compounds have the same type of coordination polyhedron (symmetry point group D3h) and very close Ln–donor atom distances. Full article
(This article belongs to the Special Issue Synthesis, Properties and Applications of Lanthanide and Actinide Molecular Compounds)
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15 pages, 3630 KB  
Article
Synthesis and Characterization of Catecholato Copper(II) Complexes with Sterically Hindered Neutral and Anionic N3 Type Ligands: Tris(3,5-diisopropyl-1-pyrazolyl)methane and Hydrotris(3,5-diisopropyl-1-pyrazolyl)borate
by Kiyoshi Fujisawa, Tetsuya Ono and Moemi Okamura
Inorganics 2020, 8(5), 37; https://doi.org/10.3390/inorganics8050037 - 18 May 2020
Cited by 7 | Viewed by 4294
Abstract
Three catecholato copper(II) complexes, [Cu(catCl4)(L1′)], [Cu(catBr4)(L1′)], and [Cu(catCl4)(L1H)], supported by sterically hindered neutral and anionic N3 type ligands: tris(3,5-diisopropyl-1-pyrazolyl)methane (referred to as L1′) and hydrotris(3,5-diisopropyl-1-pyrazolyl)borate (referred to as L1−), are synthesized and [...] Read more.
Three catecholato copper(II) complexes, [Cu(catCl4)(L1′)], [Cu(catBr4)(L1′)], and [Cu(catCl4)(L1H)], supported by sterically hindered neutral and anionic N3 type ligands: tris(3,5-diisopropyl-1-pyrazolyl)methane (referred to as L1′) and hydrotris(3,5-diisopropyl-1-pyrazolyl)borate (referred to as L1−), are synthesized and characterized in detail. Their X-ray structures reveal that both [Cu(catCl4)(L1′)] and [Cu(catBr4)(L1′)] complexes have a five-coordinate square-pyramidal geometry and [Cu(catCl4)(L1H)] complex has a four-coordinate square-planar geometry. The L1H is unusual protonated ligand that controls its overall charge. For the three catecholato copper(II) complexes, the oxidation state of copper is divalent, and catechol exists in catecholate as two minus anion. This difference in coordination geometry affects their d-d and CT transitions energy and ESR parameters. Full article
(This article belongs to the Special Issue Scorpionates: Recent Advances)
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15 pages, 2414 KB  
Article
Hydrosoluble Complexes Bearing Tris(pyrazolyl)methane Sulfonate Ligand: Synthesis, Characterization and Catalytic Activity for Henry Reaction
by Abdallah G. Mahmoud, Luísa M. D. R. S. Martins, M. Fátima C. Guedes da Silva and Armando J. L. Pombeiro
Catalysts 2019, 9(7), 611; https://doi.org/10.3390/catal9070611 - 18 Jul 2019
Cited by 11 | Viewed by 4953
Abstract
The catalytic activity of the water-soluble scorpionate coordination compounds [Cu(-NN’O-Tpms)2] (1), [Mn(Tpms)2] (2) and Li[FeCl2(-NN’N’’-Tpms)] (3) [Tpms = tris(pyrazolyl)-methane sulfonate, O3SC(pz)3], were studied towards the (Henry) reaction [...] Read more.
The catalytic activity of the water-soluble scorpionate coordination compounds [Cu(-NN’O-Tpms)2] (1), [Mn(Tpms)2] (2) and Li[FeCl2(-NN’N’’-Tpms)] (3) [Tpms = tris(pyrazolyl)-methane sulfonate, O3SC(pz)3], were studied towards the (Henry) reaction between benzaldehyde and nitromethane or nitroethane in aqueous medium to afford, respectively, 2-nitro-1-phenylethanol or 2-nitro-1-phenylpropanol, the latter in the syn and the anti diastereoisomeric forms. Complex 1 exhibited the highest activity under the optimum experimental conditions and was used to broaden the scope of the reaction to include several aromatic aldehydes achieving yields up to 94%. Full article
(This article belongs to the Special Issue Catalysts for Henry Reaction)
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17 pages, 3030 KB  
Article
Novel Methinic Functionalized and Dendritic C-Scorpionates
by Luísa M. D. R. S. Martins, Riccardo Wanke, Telma F. S. Silva, Armando J. L. Pombeiro, Paul Servin, Régis Laurent and Anne-Marie Caminade
Molecules 2018, 23(12), 3066; https://doi.org/10.3390/molecules23123066 - 23 Nov 2018
Cited by 15 | Viewed by 4491
Abstract
The study of chelating ligands is undoubtedly one of the most significant fields of research in chemistry. The present work is directed to the synthesis of new functionalized derivatives of tripodal C-scorpionate compounds. Tris-2,2,2-(1-pyrazolyl)ethanol, HOCH2C(pz)3 (1), one of [...] Read more.
The study of chelating ligands is undoubtedly one of the most significant fields of research in chemistry. The present work is directed to the synthesis of new functionalized derivatives of tripodal C-scorpionate compounds. Tris-2,2,2-(1-pyrazolyl)ethanol, HOCH2C(pz)3 (1), one of the most important derivatives of hydrotris(pyrazolyl)methane, was used as a building block for the synthesis of new functionalized C-scorpionates, aiming to expand the scope of this unexplored class of compounds. The first dendritic C-scorpionate was successfully prepared and used in the important industrial catalytic reactions, Sonogashira and Heck C-C cross-couplings. Full article
(This article belongs to the Special Issue Scorpionate Ligands: Ever-Young Chemistry Tools)
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18 pages, 2810 KB  
Article
Solventless Synthesis of Poly(pyrazolyl)phenyl-methane Ligands and Thermal Transformation of Tris(3,5-dimethylpyrazol-1-yl)phenylmethane
by Edith Rodríguez-Venegas, Efrén V. García-Báez, Francisco J. Martínez-Martínez, Alejandro Cruz and Itzia I. Padilla-Martínez
Molecules 2017, 22(3), 441; https://doi.org/10.3390/molecules22030441 - 11 Mar 2017
Cited by 1 | Viewed by 6741
Abstract
The solventless synthesis of tris(pyrazolyl)phenylmethane ligands of formula C6H5C(PzR2)3 (R = H, Me), starting from PhCCl3 and 3,5-dimethylpyrazole (PzMe2) or pyrazole (Pz) was performed. The sterically crowded C6H5C(PzMe2 [...] Read more.
The solventless synthesis of tris(pyrazolyl)phenylmethane ligands of formula C6H5C(PzR2)3 (R = H, Me), starting from PhCCl3 and 3,5-dimethylpyrazole (PzMe2) or pyrazole (Pz) was performed. The sterically crowded C6H5C(PzMe2)3 is thermally transformed into the bis(pyrazolyl)(p-pyrazolyl)phenylmethane ligand PzMe2-C6H4CH(PzMe2)2. In this compound both PzMe2 rings are linked through the N-atom to the methine C-atom. At higher temperatures, the binding mode of PzMe2 changes from N1 to C4. All transformations occurred via quinonoid carbocation intermediates that undergo an aromatic electrophilic substitution on the 4-position of PzMe2. Reaction conditions were established to obtain five tris(pyrazolyl)phenylmethane ligands in moderate to good yields. 1H- and 13C-NMR spectroscopy and X-ray diffraction of single crystals support the proposed structures. Full article
(This article belongs to the Section Organic Chemistry)
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