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Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
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Syntheses and characterization of (C2F5)3BCO and (C3F7)3BCO.

Michael Gerken1, Gottfried Pawelke, Eduard Bernhardt

  • 1Bergische Universität Wuppertal, FB C-Anorganische Chemie, Gaussstrasse 20, 42097 Wuppertal, Germany. michael.gerken@uleth.ca

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 15, 2010
PubMed
Summary

New tris(perfluoroalkyl)borane carbonyls were synthesized using a novel route. These compounds exhibit exceptionally short carbon-oxygen triple bonds and decompose to release carbon monoxide and other fluorinated byproducts.

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Area of Science:

  • Organometallic Chemistry
  • Fluorine Chemistry
  • Boron Chemistry

Background:

  • Tris(perfluoroalkyl)borane carbonyls represent a novel class of organoboron compounds.
  • Understanding their synthesis and decomposition is crucial for developing new fluorinated materials.

Purpose of the Study:

  • To synthesize new tris(perfluoroalkyl)borane carbonyls, (C(2)F(5))(3)BCO and (C(3)F(7))(3)BCO.
  • To characterize their structure and investigate their decomposition pathways.

Main Methods:

  • Novel synthetic route involving K[(perfluoroalkyl)BCOOH] precursors and concentrated sulfuric acid.
  • Oxidative cleavage of alkynyl groups in Cs[(perfluoroalkyl)BC≡CPh] intermediates.
  • X-ray crystallography for structural determination.
  • Kinetic studies to determine decomposition rate law and activation energy.

Main Results:

  • Successful synthesis of (C(2)F(5))(3)BCO and (C(3)F(7))(3)BCO.
  • Crystal structures revealed very short C≡O bond lengths (1.109(2) Å and 1.103(5) Å).
  • Decomposition at room temperature yields CO, difluoroperfluoroalkylboranes, and perfluoroalkenes.
  • Decomposition of (C(2)F(5))(3)BCO follows first-order kinetics with E(a)=107 kJ mol(-1).

Conclusions:

  • The novel synthetic route provides access to novel tris(perfluoroalkyl)borane carbonyls.
  • The short C≡O bond length suggests unique electronic properties.
  • The decomposition pathway provides insights into the stability and reactivity of these compounds.