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Configurationally rigid pentaorganosilicates.

Erik P A Couzijn1, Daniël W F van den Engel, J Chris Slootweg

  • 1Department of Chemistry and Pharmaceutical Sciences, Faculty of Sciences, VU University Amsterdam, De Boelelaan 1083, NL-1081 HV Amsterdam, The Netherlands.

Journal of the American Chemical Society
|February 24, 2009
PubMed
Summary
This summary is machine-generated.

Computational chemistry reveals two pathways for intramolecular substituent interchange in pentaorganosilicates. These findings enable the design of configurationally rigid, silicon-chiral organosilicate compounds stable at room temperature.

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Area of Science:

  • Organometallic Chemistry
  • Computational Chemistry
  • Stereochemistry

Background:

  • Pentaorganosilicates are a class of silicon compounds with potential applications in materials science.
  • Understanding their dynamic behavior, such as substituent interchange, is crucial for designing stable structures.

Purpose of the Study:

  • To investigate the mechanisms of intramolecular substituent interchange in pentaorganosilicates.
  • To correlate computational findings with experimental data.
  • To design and synthesize novel, configurationally rigid organosilicates.

Main Methods:

  • Density Functional Theory (DFT) calculations, specifically B3LYP functional.
  • Intramolecular Reaction Coordinate (IRC) calculations.
  • Synthesis of novel methyl- and ethylbis([2]naphthylpyrrol-2,1'-diyl)silicate compounds.

Main Results:

  • Two distinct ligand permutation pathways (A and B) were identified, both leading to racemization.
  • Pathway A involves enantiomeric paths and is hindered by ortho substitution.
  • Pathway B proceeds via a trigonal bipyramidal transition state and is sensitive to ligand electronic properties.
  • Electronegative substituents influence the energy barriers of both pathways.
  • Novel Si-chiral pentaorganosilicates were synthesized and found to be configurationally rigid.

Conclusions:

  • The study elucidates the stereomutation mechanisms in pentaorganosilicates.
  • Computational insights guided the successful synthesis of stable, chiral organosilicate compounds.
  • The findings contribute to the development of new chiral silicon-based materials.