ChemInform Abstract: Synthesis and Structure of Diorganyldiaryloxytelluranes with Intramolecular Te···N Coordination Bonds.

Maksimenko, A. A.; Mehrotra, Gopal K.; Maslakov, A. G.; Kompan, O. E.; Sadekov, I. D.; Struchkov, Yu. T.; Yufit, D. S.

doi:10.1002/chin.198849209

Cited by 6 publications

(6 citation statements)

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“…All newly synthesized compounds were characterized by 125 Te and 1 H NMR spectroscopy, the former being known for extreme sensitivity to the geometry and the electronic environment of tellurium [1,9,13,[41][42][43][44]. The d 125 Te and d 1 H chemical shift data are listed in Table 10.…”

Section: Te and 1 H Nmr Spectramentioning

confidence: 99%

Synthesis and structure of N-arylimines of β-tellurocyclohexenals with the intramolecular coordination N→Te bonds

Sadekov

Захаров

Starikov

et al. 2005

Journal of Organometallic Chemistry

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Section: Te and 1 H Nmr Spectramentioning

confidence: 99%

Synthesis and structure of N-arylimines of β-tellurocyclohexenals with the intramolecular coordination N→Te bonds

Sadekov

Захаров

Starikov

et al. 2005

Journal of Organometallic Chemistry

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“…The stabilization of these tellurium compounds often relied on the judicious choice of aryl substituents containing intramolecularly coordinating N(sp 3 )‐donor ligands, such as the “one‐arm” 2‐dialkylaminomethylphenyl group ( I ), the “two‐arm” 2,6‐bis(dialkylaminomethylphenyl) group ( II ), and the “stiff‐arm” 8‐dialkylaminonaphthyl group ( III , Scheme ) , . These ligands are complemented by aryl substituents containing intramolecularly coordinating N(sp 2 )‐donor ligands, such as the 2‐pyridylphenyl group ( IV ), the 2‐oxazolinylphenyl group ( V ),, and the 2‐iminomethylphenyl group ( VI , Scheme ) , . The ligands I – V are usually prepared by N‐directed ortho ‐ or peri ‐lithiation of the aromatic systems through C–H/Li or C–Br/Li exchange reactions .…”

Section: Introductionmentioning

confidence: 99%

Intramolecularly Coordinated 2‐Iminomethylphenyltellurium Compounds

et al. 2017

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Procedures for the synthesis of 2-(tBuNCH)-C 6 H 4 Te(S 2 CNEt 2 ) (1a), 2-(2′,6′-iPr 2 C 6 H 3 NCH)C 6 H 4 Te(S 2 CNEt 2 ) (1b), [2-(tBuNCH)C 6 H 4 ] 2 Te (2a), 2-(tBuNCH)C 6 H 4 TeCl (3a), and 2-(tBuNCH)C 6 H 4 TeCl 3 (4a) have been developed. Compounds 1a-4a possess 2-iminomethylphenyl groups that provide intramolecular N donation to the Te atoms, which was investigated by multinuclear NMR spectroscopy and X-ray crystallography. The Te-N bond lengths increase in the order 3a [2.203 (2) Å] < 4a [2.286(1) Å] < 1b [2.337(2) Å] < 1a [2.407(2) Å] < 2a [a] 3435 Scheme 1. Tellurium compounds stabilized by intramolecular N(sp 3 ) donation (top row) and N(sp 2 ) donation (bottom row). Full PaperScheme 2. General route for the synthesis of 2-iminomethylphenyltellurium compounds reported in the literature. analyzed through DFT calculations and real-space bonding indicators (RSBI), which are derived from the computed electron and pair densities. Topological dissection of the electron density (ED) according to the atoms-in-molecules (AIM) space-partitioning scheme [88] provides a bond-path motif that resembles the molecular structure as well as details of atomic properties such as charges and volumes. Analysis of the reduced density gradient, s(r) = [1/2(3π 2 ) 1/3 ]|∇ρ|/ρ 4/3 , according to the recently introduced noncovalent interactions (NCI) index [89] affords noncovalent bonding aspects. Notably, the assignment of different contact types, including steric/repulsive (λ 2 > 0), van der Waals like (λ 2 ≈ 0), and attractive (λ 2 < 0) interactions is facilitated by mapping the product of the ED and the sign of the second eigenvalue of the Hessian [sign(λ 2 )ρ] on the isosurfaces of s(r). Finally, topological dissection of the pair density according to the electron localizability indicator (ELI-D) [90] provides core, bonding, and lone-pair basins, which are especially valuable for the analysis of covalent (including dative) bonds. ELI-D isosurfaces (localization domain representations of the basins) and NCI isosurfaces show a complementary spatial distribution, [91] which suggests spatial separation of covalent and noncovalent bonding aspects, which has been a matter of recent debate. [92] The combination of AIM, NCI, and ELI-D thus allows the monitoring of minute electronic changes in the Te-N interaction, which is dominated by covalent bonding aspects for short Te-N distances and ionic bonding aspects for longer Te-N distances. These calculations extend previous computational studies on intramolecularly coordinated N-donor tellurium compounds by us [93] and others. [94,95] Scheme 3. Synthesis of 1a-4a and 1b.

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“…This approach has been further extended to the synthesis of a range of ortho -tellurated derivatives of the same ligand and to the other ligands carrying potentially chelating ortho substituents, such as 2-(2-pyridyl)phenyl, azomethine, and related systems to isolate novel monomeric, stable organotellurium compounds and to study the nature of interactions between the tellurium and nitrogen atom. Minkin and co-workers have extensively studied the synthesis, reactions, and structures of ortho -tellurated derivatives of azomethines with intramolecular tellurium−nitrogen coordinate bonds. The ligands bearing an oxygen donor atom have also been used for the synthesis of stable organotellurium compounds .…”

Section: Introductionmentioning

confidence: 99%

Influence of Both Steric Effects and Te···N Intramolecular Nonbonded Interactions on the Stabilization of Organotellurium Compounds Incorporating [2-[1-(3,5-Dimethylphenyl)-2- naphthyl]-4,5-dihydro-4,4-dimethyloxazole]

et al. 2003

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A series of novel low-valent organotellurium compounds incorporating [2-[1-(3,5-dimethylphenyl)-2-naphthyl]-4,5-dihydro-4,4-dimethyloxazole] (1) stabilized by Te‚‚‚N nonbonded interactions have been synthesized. The synthesis has been achieved by the ortholithium route. The lithium arenetellurolate 3 was obtained by direct metalation of 1 with 1.6 M of n-BuLi in hexane followed by the insertion of tellurium into the Li-C bond. Oxidation of 3 then afforded the desired ditelluride 4. The reaction of 4 with a stoichiometric amount of sulfuryl chloride yielded stable tellurenyl(II) chloride 5, whereas the addition of an excess sulfuryl chloride led to the formation of tellurium(IV) trichloride 6. The stable bromo compound 7 was obtained by the controlled bromination of 4 with bromine. No tellurium tribromide formation was observed when the ditelluride was treated with an excess of bromine. Compound 4 underwent facile reaction with a stoichiometric amount of iodine to give a stable mono iodo compound (8). The phenyltelluride derivative 9 was obtained by the treatment of lithiated product 2 with PhTeBr at low temperature. Attempts to synthesize the symmetrical telluride of the type R 2 Te (10) by the reaction of 2 with Te(dtc) 2 (dtc ) diethyldithiocarbamate) or TeI 2 were unsuccessful. All compounds were characterized by elemental analysis, multinuclear ( 1 H, 13 C, 125 Te) NMR, and mass spectrometry techniques. The presence of strong Te‚‚‚N intramolecular nonbonded interactions in all the compounds was confirmed by single-crystal X-ray crystallographic studies.

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ChemInform Abstract: Synthesis and Structure of Diorganyldiaryloxytelluranes with Intramolecular Te···N Coordination Bonds.

Abstract: The title compounds (III) are prepared by an exchange reaction of the diorganyldimethoxytelluranes (I), obtained via treatment of the corresponding diorganyltellurium dihalogenides with sodium methoxide, with the phenols (II).

Cited by 6 publications

References 1 publication

Synthesis and structure of N-arylimines of β-tellurocyclohexenals with the intramolecular coordination N→Te bonds

Synthesis and structure of N-arylimines of β-tellurocyclohexenals with the intramolecular coordination N→Te bonds

Intramolecularly Coordinated 2‐Iminomethylphenyltellurium Compounds

Influence of Both Steric Effects and Te···N Intramolecular Nonbonded Interactions on the Stabilization of Organotellurium Compounds Incorporating [2-[1-(3,5-Dimethylphenyl)-2- naphthyl]-4,5-dihydro-4,4-dimethyloxazole]

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