Innovative synthetical and structural features of new aryltellurenyl iodides

Faoro, Eliandro; Oliveira, Gelson Manzoni de; Lang, Ernesto Schulz; Pereira, Camila Bugnotto

doi:10.1016/j.jorganchem.2011.03.012

Cited by 12 publications

(6 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Te product of the phenyl group migration, the unsymmetrical diaryltelluride MesPhTe, was identified in the mother liquor by its 125 Te NMR chemical shift (419.7 ppm) after most of the Mes 2 Te and 4 were removed by crystallization. To support the identification, MesTePh (a colorless oil), was independently prepared by the reaction of MesTeI (obtained in situ by the reaction of MesTeTeMes with iodine) with PhMgBr. More efficiently, 4 was prepared by the one-pot reaction of Mes 2 Te, Ph 3 Sb, and HO 3 SCF 3 and isolated in 92% yield.…”

Section: Resultsmentioning

confidence: 99%

Mesityltellurenyl Cations Stabilized by Triphenylpnictogens [MesTe(EPh₃)]⁺ (E = P, As, Sb)

et al. 2012

View full text Add to dashboard Cite

The homoleptic 1:1 Lewis pair (LP) complex [MesTe(TeMes2)]O3SCF3 (1) featuring the cation [MesTe(TeMes2)](+) (1a) was obtained by the reaction of Mes2Te with HO3SCF3. The reaction of 1 with Ph3E (E = P, As, Sb, Bi) proceeded with substitution of Mes2Te and provided the heteroleptic 1:1 LP complexes [MesTe(EPh3)]O3SCF3 (2, E = P; 3, E = As) and [MesTe(SbPh3)][Ph2Sb(O3SCF3)2] (4) featuring the cations [MesTe(EPh3)](+) (2a, E = P; 3a, E = As; 4a, E = Sb) and the anion [Ph2Sb(O3SCF3)2](-) (4b). In the reaction with Ph3Bi, the crude product contained the cation [MesTe(BiPh3)](+) (5a) and the anion [Ph2Bi(O3SCF3)2](-) (5b); however, the heteroleptic 1:1 LP complex [MesTe(BiPh3)][Ph2Bi(O3SCF3)2] (5) could not be isolated because of its limited stability. Instead, fractional crystallization furnished a large amount of Ph2BiO3SCF3 (6), which was also obtained by the reaction of Ph3Bi with HO3SCF3. The formation of the anions 4b and 5b involves a phenyl group migration from Ph3E (E = Sb, Bi) to the MesTe(+) cation and afforded MesTePh as the byproduct, which was identified in the mother liquor. The heteroleptic 1:1 LP complexes 2-4 were also obtained by the one-pot reaction of Mes2Te, Ph3E (E = P, As, Sb) and HO3SCF3. Compounds 1-4 and 6 were investigated by single-crystal X-ray diffraction. The molecular structures of 1a-4a were used for density functional theory calculations at the B3PW91/TZ level of theory and studied using natural bond order (NBO) analyses as well as real-space bonding descriptors derived from an atoms-in-molecules (AIM) analysis of the theoretically obtained electron density. Additionally, the electron localizability indicator (ELI-D) and the delocalization index are derived from the corresponding pair density.

show abstract

Section: Resultsmentioning

confidence: 99%

Mesityltellurenyl Cations Stabilized by Triphenylpnictogens [MesTe(EPh₃)]⁺ (E = P, As, Sb)

et al. 2012

View full text Add to dashboard Cite

show abstract

“…The shortening of the XB length with arsenic acceptors is not as drastic as for phosphorus acceptors, and the elongation of the I–I distances is also lower (I–I 2.95 Å for the ortho and 3.04 Å for the para derivatives). Tellurium acceptors have recently been found in seven structures33 and five of them contain rather short I ··· Te distances, namely 2.83 (FUSWAS),33a 2.85 (VUVYAN), 2.90 (VUVXOA), 2.98 (VUVYIV),33b and 2.89 Å (CCDC‐805866)33c (26–30 % reduction), as well as significantly lengthened I–I distances (2.92–3.10 Å). The sixth structure with two Te centres shows slightly longer I ··· Te bonds (3.03 and 3.06 Å, 25 and 24 % reduction, CCDC‐805867) and also slightly shorter I–I distances (2.88 and 2.86 Å, respectively) 33c.…”

Section: Halogen Bonding With Organic Molecules In the Solid Statementioning

confidence: 99%

“…Tellurium acceptors have recently been found in seven structures33 and five of them contain rather short I ··· Te distances, namely 2.83 (FUSWAS),33a 2.85 (VUVYAN), 2.90 (VUVXOA), 2.98 (VUVYIV),33b and 2.89 Å (CCDC‐805866)33c (26–30 % reduction), as well as significantly lengthened I–I distances (2.92–3.10 Å). The sixth structure with two Te centres shows slightly longer I ··· Te bonds (3.03 and 3.06 Å, 25 and 24 % reduction, CCDC‐805867) and also slightly shorter I–I distances (2.88 and 2.86 Å, respectively) 33c. The final structure shows a Te ··· I–I ··· Te assembly with a significantly longer I ··· Te distance of 3.22 Å (20 % reduction, MOMXAO) and the weakest lengthening of the I–I bond (2.85 Å) 33d.…”

Section: Halogen Bonding With Organic Molecules In the Solid Statementioning

confidence: 99%

Alternative Motifs for Halogen Bonding

et al. 2013

View full text Add to dashboard Cite

The halogen‐bonding interaction is one of the rising stars in supramolecular chemistry. Although other weak interactions and their influence on the structure and chemistry of various molecules, complexes and materials have been investigated thoroughly, the field of halogen bonding is still quite unexplored and its impact on chemistry in general is yet to be fully revealed. In principle, every Y–X bond (Y = electron‐withdrawing atom or moiety, X = halogen atom) can act as a halogen‐bond donor when the halogen is polarized enough by Y. Perfluorohalocarbons are iconic halogen‐bond donor molecules in which Y is a perfluorinated aryl or alkyl moiety and X is either iodine or bromine. In this article, alternative halogen‐bond motifs such as X2···A and Ar–X···A [A = Lewis basic halogen‐bond‐accepting atom of a molecule or ion; Ar = neutral or charged (hetero)aromatic system] are reviewed. In addition, haloalkenes, haloalkynes, N‐haloamides and other non‐metallic halogen‐bond donors and their respective halogen‐bonded structures will also be described. Although purely organic halogen‐bonding motifs are very prominent, the role of metal complexes in halogen bonding is becoming increasingly evident as well, which is also reflected in this review. Finally, halogen bonding in solution is briefly highlighted. Contemporary research is proving that halogen bonding is more than a solid‐state phenomenon and is now a well‐recognized weak interaction in chemistry.

show abstract

“…Chemical diagrams for tellurium(II) compounds described herein, 125-151, 82,[125][126][127][128][129][130][131][132][133][134][135][136][137][138] forming…”

Section: Zero-and One-dimensional Aggregates Sustained By Te(ii) … π(mentioning

confidence: 99%

Main group metal lone-pair⋯π(arene) interactions: a new bonding mode for supramolecular associations

et al. 2016

View full text Add to dashboard Cite

Crystal structures of the heavier main group elements in low oxidation states have been evaluated for the presence of supramolecular element(lp)⋯π(arene) interactions that are structure-directing. It is revealed that when present, these interactions lead to zerodimensional, binuclear aggregates but higher-nuclearity species are sometimes observed, with one-dimensional supramolecular chains of varying topology being prominent. By contrast, two-dimensional aggregation based on element(lp)⋯π(arene) interactions are rare. In summary, interactions of main group metal lone-pairs with aromatic rings are revealed as synthons capable of assembling molecules into supramolecular aggregates. † Electronic supplementary information (ESI) available: For ESI (illustrations of supramolecular aggregation based on main group element(lone-pair)⋯π(arene) interactions for 1-157), see DOI:

show abstract

Innovative synthetical and structural features of new aryltellurenyl iodides

Cited by 12 publications

References 31 publications

Mesityltellurenyl Cations Stabilized by Triphenylpnictogens [MesTe(EPh₃)]⁺ (E = P, As, Sb)

Mesityltellurenyl Cations Stabilized by Triphenylpnictogens [MesTe(EPh₃)]⁺ (E = P, As, Sb)

Alternative Motifs for Halogen Bonding

Main group metal lone-pair⋯π(arene) interactions: a new bonding mode for supramolecular associations

Contact Info

Product

Resources

About

Innovative synthetical and structural features of new aryltellurenyl iodides

Cited by 12 publications

References 31 publications

Mesityltellurenyl Cations Stabilized by Triphenylpnictogens [MesTe(EPh3)]+ (E = P, As, Sb)

Mesityltellurenyl Cations Stabilized by Triphenylpnictogens [MesTe(EPh3)]+ (E = P, As, Sb)

Alternative Motifs for Halogen Bonding

Main group metal lone-pair⋯π(arene) interactions: a new bonding mode for supramolecular associations

Contact Info

Product

Resources

About

Mesityltellurenyl Cations Stabilized by Triphenylpnictogens [MesTe(EPh₃)]⁺ (E = P, As, Sb)

Mesityltellurenyl Cations Stabilized by Triphenylpnictogens [MesTe(EPh₃)]⁺ (E = P, As, Sb)