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Chalcogen Bonding with Diaryl Ditellurides: Evidence from Solid State and Solution Studies.

Robin Weiss1, Emmanuel Aubert2, Loic Groslambert1

  • 1Institute of Chemistry of Strasbourg, UMR 7177 - LASYROC, CNRS and Strasbourg University, 4 rue Blaise Pascal, 67000, Strasbourg, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 18, 2022
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Summary
This summary is machine-generated.

Chalcogen bonding in diaryl ditellurides reveals unique tellurium (Te) σ-hole interactions. These interactions lead to novel solid-state structures and measurable Lewis acidity, quantified using NMR spectroscopy.

Keywords:
125Te NMRchalcogen bonddiaryl ditelluridesupramolecular interactionσ-hole

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Area of Science:

  • Supramolecular Chemistry
  • Organotellurium Chemistry
  • Non-covalent Interactions

Background:

  • Chalcogen bonding (ChB) is an important non-covalent interaction involving the electropositive σ-hole of a chalcogen atom.
  • Tellurium (Te) exhibits unique electronic properties, making its ChB ability a subject of interest.
  • Diaryl ditellurides (ArTeTeAr) offer multiple potential sites for ChB due to the presence of two Te atoms.

Purpose of the Study:

  • To investigate the chalcogen bonding ability of tellurium in symmetrical diaryl ditellurides.
  • To elucidate the factors governing the regioselectivity of Te σ-hole interactions.
  • To characterize the structural consequences and Lewis acidity of these tellurium compounds.

Main Methods:

  • Computational calculations to determine the electropositive nature of Te σ-holes.
  • X-ray crystallography to analyze solid-state structures formed via intermolecular Te⋅⋅⋅Te ChB.
  • Nuclear Magnetic Resonance (NMR) spectroscopy (125Te and 19F-1H HOESY) to evaluate Lewis acidity and monitor interactions with Lewis bases (R3PO).

Main Results:

  • The Te σ-hole along the less polarized Te-Te bond was found to be more electropositive than the one along the Te-Ar bond, attributed to hyperconjugation.
  • Intermolecular Te⋅⋅⋅Te ChB interactions resulted in unique solid-state motifs, including Te4 rectangles and Te3 triangles.
  • 125Te NMR confirmed Te⋅⋅⋅O interactions, yielding association constants (Ka) up to 90 M-1 for 1:1 adducts, with the highest affinity observed for CF3-substituted ArTeTeAr and Et3PO.

Conclusions:

  • Diaryl ditellurides exhibit significant chalcogen bonding capabilities, influencing their solid-state assembly.
  • The electronic interplay between Te lone pairs and σ* orbitals dictates the site of interaction.
  • NMR spectroscopy provides a reliable method for quantifying the Lewis acidity and interaction strength of tellurium σ-holes.