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Related Experiment Videos

Resonance-assisted intramolecular chalcogen-chalcogen interactions?

Pablo Sanz1, Manuel Yáñez, Otilia Mó

  • 1Departamento de Quimica C-9, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 23, 2003
PubMed
Summary

Intramolecular hydrogen bonds and chalcogen-chalcogen interactions in saturated aldehydes are weaker than in unsaturated ones. These nonbonding interactions involving selenium and tellurium are not always strongly stabilizing.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Organic Chemistry

Background:

  • Chalcogenoaldehydes are organic compounds containing carbon, hydrogen, and chalcogen elements (O, S, Se, Te).
  • Intramolecular interactions, such as hydrogen bonds and chalcogen-chalcogen bonds, play a significant role in molecular structure and properties.
  • Understanding these interactions is crucial for predicting chemical reactivity and designing new materials.

Purpose of the Study:

  • To investigate the nature and strength of intramolecular hydrogen bonds (IHBs) and chalcogen-chalcogen interactions in saturated chalcogenoaldehydes.
  • To compare these interactions with those found in unsaturated analogues.
  • To elucidate the factors influencing the stability of different tautomers and conformers.

Main Methods:

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  • High-level B3LYP/6-311+G(3df,2p) density functional calculations were employed.
  • A series of saturated chalcogenoaldehydes with the general formula CH(X)-CH(2)-CH(2)YH (X, Y=O, S, Se, Te) were studied.
  • Energetic analysis of different tautomers and conformers was performed.

Main Results:

  • In saturated X=Y=O, S, Se aldehydes, the X-H...X IHB competes with X...XH chalcogen-chalcogen interaction.
  • For tellurium analogues, chalcogen-chalcogen interaction is dominant.
  • Intramolecular and chalcogen-chalcogen interactions in saturated compounds are significantly weaker than in unsaturated analogues, with exceptions for specific conformers involving tellurium.
  • Resonance effects in unsaturated compounds enhance these interactions, similar to Resonance Assisted Hydrogen Bonds (RAHB).

Conclusions:

  • Nonbonding interactions involving selenium and tellurium are not always strongly stabilizing in saturated systems.
  • The strength of these interactions is highly dependent on the specific chalcogen atoms involved and the degree of saturation.
  • Charge delocalization and molecular environment significantly influence the strength of chalcogen-chalcogen interactions, particularly in unsaturated systems.