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Lewis Acids and Bases02:33

Lewis Acids and Bases

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In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
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This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...
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Lewis Structures of Molecular Compounds and Polyatomic Ions02:54

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Non-Innocent Methylene Linker in Bridged Lewis Pair Initiators.

Michael Weger1, Raphael K Grötsch1, Maximilian G Knaus1

  • 1Catalysis Research Center & WACKER-Chair of Macromolecular Chemistry, Technical University of Munich, Lichtenbergstrasse 4, 85748, Garching, Germany.

Angewandte Chemie (International Ed. in English)
|May 3, 2019
PubMed
Summary

Researchers discovered that deprotonation, previously an unwanted side reaction, is the key initiation pathway for aluminum-phosphorus-based bridged Lewis pair (Al-P BLP) polymerization of Michael acceptors. This finding enables controlled polymerization with high activity and living characteristics.

Keywords:
Lewis pairsMichael-type monomersX-ray diffractionneutron diffractionpolymerization

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Area of Science:

  • Polymer Chemistry
  • Organometallic Chemistry
  • Materials Science

Background:

  • Lewis pair polymerization typically initiates via conjugate addition of a Lewis base to an activated monomer.
  • Deprotonation is generally considered an undesirable side reaction in such polymerizations, particularly with Boron-Phosphorus based bridged Lewis pairs (B-P BLPs).
  • Previous studies on B-P BLPs forming macrocyclic products did not identify deprotonation as an initiation mechanism.

Purpose of the Study:

  • To investigate the initiation mechanism of Aluminum-Phosphorus-based bridged Lewis pair (Al-P BLP) polymerization of Michael acceptors.
  • To explore the role of the methylene bridge in Al-P BLP-mediated polymerization.
  • To evaluate the polymerization behavior, including activity, control, and copolymerization capabilities, of Al-P BLPs.

Main Methods:

  • Synthesis and characterization of a series of Al-P-based bridged Lewis pairs (BLPs).
  • Single-crystal diffraction experiments (X-ray and neutron diffraction) to determine structural properties.
  • Mechanistic investigations employing both experimental techniques and computational modeling.
  • Polymerization studies to assess living behavior, activity, molecular weight distribution, and copolymerization potential.

Main Results:

  • The study identified deprotonation as the primary initiation pathway for Al-P BLP polymerization, contrary to previous assumptions.
  • The methylene bridge within the Al-P BLP was found to act as a base, facilitating the deprotonation of α-acidic monomers.
  • Al-P BLP polymerization exhibited living characteristics, high catalytic activity, narrow molecular mass distributions, and demonstrated copolymerization capabilities.

Conclusions:

  • Deprotonation, facilitated by the methylene bridge of Al-P BLPs, is the dominant initiation mechanism in the polymerization of Michael acceptors.
  • This mechanistic insight allows for the development of highly active and controlled polymerization systems using Al-P BLPs.
  • The demonstrated living polymerization and copolymerization abilities open avenues for synthesizing advanced polymer architectures.