Bis[(4-methylphenyl)ethynyl] telluride

Caracelli, Ignez; Zukerman-Schpector, Júlio; Pena, Jesus M.; Stefani, Hélio A.; Tiekink, Edward R. T.

doi:10.1107/s1600536810006264

Cited by 3 publications

(7 citation statements)

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“…The Te-C distance in Na 2 TeC 2 is 2.333 Å, which is somewhat larger than the (Pd/Pt)-C distances in Na 2 (Pd/Pt)C 2 (z2 Å), and in bis[(4-methylphenyl) ethynyl] telluride (2.045 Å). 20 The C^C bond length in Na 2 TeC 2 is shorter than in Na 2 (Pd/Pt)C 2 , this is also indicated by the greater vibrational wavenumber.…”

Section: Resultsmentioning

confidence: 93%

“…The rst step of this reaction is familiar from analogous acetylenic organo-telluride reactions when the H of ATeC 2 H is replaced by an organic functional group, typically an arene. 14,15,20 The second step may largely complete when the solvent NH 3 is evaporated along with the acetylene gas, with the possibility that the rest of the acetylene gas is removed when the product is ground in a mortar. A repeated condensation of NH 3 and sonication of the mixture, followed by repeated evaporation of NH 3 helps to better mix the reaction components and remove as much residual acetylene gas as possible, before grinding the product in a mortar.…”

Section: Resultsmentioning

confidence: 99%

“…10 The short, 1.727 Å, Te-C distance in Li 2 TeC 2 should also be interpreted as a projected distance, while the long, 2.333 Å, Te-C distance in Na 2 TeC 2 is closer to expectations based on DFT predictions. 13 The Te-C distance in bis[(4-methylphenyl) ethynyl] telluride is 2.045 Å, 20 while it is expected to be about 2.4 Å in ternary acetylides with Te on the basis of DFT calculations, assuming the P 3m1 space group. 13 The observed and DFT-predicted lattice parameters of Li We have explored such structural models with 1/6 probability for Li and carbon positions using the P6/mmm space group or closely related ones, however the resulting ts were signicantly This journal is © The Royal Society of Chemistry 2015 less good than the one with the P 3m1 space group.…”

Section: Resultsmentioning

confidence: 99%

“…2.5 Synthesis of Ph-C^C-Te-C^C-Ph and its double lithiated form Bis(phenylethynyl)telluride, Ph-C^C-Te-C^C-Ph, was synthesized following the procedure of ref. 20, starting from phenylacetylene (Sigma-Aldrich). We have also attempted to synthesize its double lithiated form, in analogy to the A 2 TeC 2 ternary acetylides, reacting Li-Ph-acetylide (Ph-C^C À Li + ) with Te powder in a 2 : 1 molar ratio in a sonicated dry THF solution.…”

Section: Synthesis Of Tellurium Acetylide Tecmentioning

confidence: 99%

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The synthesis of ternary acetylides with tellurium: Li₂TeC₂ and Na₂TeC₂

et al. 2015

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Tellurium Acetylide Tecmentioning

confidence: 99%

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The synthesis of ternary acetylides with tellurium: Li₂TeC₂ and Na₂TeC₂

et al. 2015

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“…21 The tellurium atom is located on a crystallographic twofold axis with the C-Te-C angle being 92.23 (15)°. The dihedral angle formed between the phenyl rings is 87.27 (7)° (Figure 3).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1,3-diynes via detelluration of bis(ethynyl)tellurides

Stefani

Pena

Zukerman-Schpector

et al. 2011

J. Braz. Chem. Soc.

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Neste artigo é descrita a síntese de sistemas diínicos conjugados contendo substituintes elétron-atratores e elétron-doadores via a deteluração catalizada por paládio de bis-(ariletinil)teluretos e bis-(alquiletinil)teluretos. Este procedimento foi realizado sob condições atmosféricas em DMF usando Pd(Oac) 2 como catalisador e AgOAc como um aditivo na presença de trietilamina. Esta rota oferece acesso eficiente a sistemas diínicos conjugados em um curto período de tempo. A estrutura cristalográfica por difração de raios X do telureto de bis(p-toluiletinila) e a conformação no estado sólido mostram uma cadeia supramolecular alinhada ao longo do eixo b, sustentada por interações CH…p.The synthesis of symmetric conjugated diyne systems with electron-withdrawing or electrondonating substituents via a palladium-catalyzed detelluration of bis(arylethynyl)tellurides and bis(alkylethynyl)tellurides is described. This procedure is effected under atmospheric conditions in DMF using Pd(OAc) 2 as a catalyst and AgOAc as an additive in the presence of triethylamine. This route offers efficient access to conjugated diyne systems in short reaction time. X-ray crystallographic structure and solid-state conformation of bis(p-tolylethynyl)telluride show a supramolecular chain aligned along the b axis, sustained by C-H…p interactions.Keywords: tellurium, bis(phenylethynyl)tellurides, bis(alkynylethynyl)tellurides, detelluration, diynes, palladium IntroductionOrganotellurium compounds play an important role in organic synthesis, and they have received considerable attention because of their potential availability and useful biological activity. 1 As reported by Bergman and co-workers 2 more than three decades ago, aryltelluriums undergo detelluration upon treatment with degassed Raney nickel to afford biaryl compounds. Although the reaction is interesting and synthetically useful, the necessity of more than a stoichiometric amount of the required metal is still a serious drawback. However, attempted transition metalcatalyzed detellurations have been unsuccessful to date. 2,3 Compounds containing chains of conjugated triple bonds 4,5 are of paramount importance as versatile and useful building blocks in organic synthesis. Among these compounds, 1,3-butadiynes 6 have been prominently utilized as substructures in the formation of valuable intermediates for natural products 7 and pharmaceuticals such as antitumor, 8 antibacterial, 9 anti-inflammatory, 10 and antifungal agents. 11 These conjugated diynes also serve as the core functional group in organic molecular materials such as linearly σ-conjugated acetylenic oligomers and polymers, 12 macrocycles 13 (Figure 1), and supramolecular scaffolds. 14 Oxidative dimerization of sp-hybridized terminal alkynes mediated by Cu(I) or Cu(II) salts under either catalytic or stoichiometric conditions is the most commonly used synthetic methodology for obtaining symmetrically substituted 1,3-butadiyne.These approaches include Glaser's coupling, 15 Eglinton's coupling, 16 and Hay's coupling. 17 In t...

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Quantitative Investigation of Intermolecular Te···A (A = π/Te/H) Interactions in Organotellurium Compounds from the Cambridge Structural Database

Majhi,

Lohar,

Meena

et al. 2023

Crystal Growth & Design

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Chalcogen bonds, which involve the interaction of an electrophilic region associated with a chalcogen atom and a nucleophilic region in an adjacent atom, have emerged as a new frontier in supramolecular chemistry. In this study, the formation of tellurium (Te)-containing chalcogen bonds along with weak hydrogen-bonds has been demonstrated, via an investigation of the crystal structures, obtained from the Cambridge Structural Database (CSD). A statistical analysis of the occurrence of short and directional tellurium-centered contacts in organic molecules, namely, Te•••Te, Te•••C, and Te•••H−C, has been performed. This was followed by the analysis of molecular electrostatic potentials, a Hirshfeld surface analysis, the three-dimensional deformation densities, and the energetics associated with the existence of different interactions in tellurium-containing molecules, having a diverse array of functional groups. Our findings indicate that Te functions as a σ-hole chalcogen bond donor, engaging with the nucleophilic π-rich system that functions as a chalcogen bond acceptor. This is an important supramolecular feature that governs the packing of molecules in the crystalline state, in addition to the presence of other tellurium-centered contacts. Thus, the current study is an attempt to consider the potential of Te-containing compounds, showing simultaneous chalcogen bond "donor" and "acceptor" characteristics, in the design of new materials.

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Bis[(4-methylphenyl)ethynyl] telluride

Cited by 3 publications

References 11 publications

The synthesis of ternary acetylides with tellurium: Li₂TeC₂ and Na₂TeC₂

The synthesis of ternary acetylides with tellurium: Li₂TeC₂ and Na₂TeC₂

Synthesis of 1,3-diynes via detelluration of bis(ethynyl)tellurides

Quantitative Investigation of Intermolecular Te···A (A = π/Te/H) Interactions in Organotellurium Compounds from the Cambridge Structural Database

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Bis[(4-methylphenyl)ethynyl] telluride

Cited by 3 publications

References 11 publications

The synthesis of ternary acetylides with tellurium: Li2TeC2 and Na2TeC2

The synthesis of ternary acetylides with tellurium: Li2TeC2 and Na2TeC2

Synthesis of 1,3-diynes via detelluration of bis(ethynyl)tellurides

Quantitative Investigation of Intermolecular Te···A (A = π/Te/H) Interactions in Organotellurium Compounds from the Cambridge Structural Database

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The synthesis of ternary acetylides with tellurium: Li₂TeC₂ and Na₂TeC₂

The synthesis of ternary acetylides with tellurium: Li₂TeC₂ and Na₂TeC₂