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Related Experiment Videos

Zwitterionic silenes: interesting goals for synthesis?

Henrik Ottosson1

  • 1Department of Organic Chemistry, Institute of Chemistry Box 599, Uppsala University, 751 24 Uppsala, Sweden. Henrik.Ottosson@kemi.uu.se

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 4, 2003
PubMed
Summary

Quantum-chemical calculations reveal that silenes with reversed silicon-carbon bond polarity exhibit zwitterionic characteristics. These unique silenes show lower dimerization heats and enable the computational design of chiral centers for organic synthesis.

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Area of Science:

  • Organometallic Chemistry
  • Computational Chemistry
  • Organic Synthesis

Background:

  • Silene chemistry is crucial for organic synthesis.
  • Understanding silicon-carbon bond polarity is key to designing novel silene structures.

Purpose of the Study:

  • To identify silenes with potential applications in organic synthesis.
  • To examine silene properties as a function of reversed silicon-carbon bond polarity.

Main Methods:

  • Quantum-chemical calculations using B3LYP, CASSCF, MP2, MP4(SDQ), and CCSD(T) methods.
  • Analysis of Z(2)Si=CXY compounds with varying Si and C substituents.
  • Charge at the silicon atom (q(Si)) as a measure of reversed polarity.

Main Results:

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  • Silenes with strong pi-donating C substituents exhibit zwitterionic (reverse-polarized) character.
  • Zwitterionic silenes feature single Si=C bonds, pyramidal Si atoms, and reduced heats of dimerization.
  • Inversion barriers increase with electron-withdrawing groups, allowing for chiral center design.

Conclusions:

  • Zwitterionic silenes possess distinct properties relevant to organic synthesis.
  • Computational design can yield chiral zwitterionic silenes for synthetic applications.
  • This study provides insights into structure-property relationships in silenes.