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Lewis Acids and Bases02:16

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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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Müller versus Gutmann-Beckett for assessing the Lewis acidity of boranes.

Sameera Ranasinghe1, Yijie Li1, Madison E Andrews1

  • 1Department of Chemistry and Biochemistry, Baylor University, One Bear Place #97348, Waco, TX 76798, USA. caleb_d_martin@baylor.ed.

Chemical Communications (Cambridge, England)
|June 12, 2025
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Summary
This summary is machine-generated.

This study introduces p-fluorobenzonitrile as a novel 19F NMR probe for assessing borane Lewis acidity. The new scale aligns well with established methods and computational data, offering a valuable tool for chemists.

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Area of Science:

  • Organometallic Chemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Lewis acidity is a fundamental property of boranes, crucial for understanding their reactivity.
  • Existing methods for quantifying Lewis acidity, such as the Gutmann-Beckett scale, have limitations.
  • Nuclear Magnetic Resonance (NMR) spectroscopy offers sensitive detection of Lewis acid-base interactions.

Purpose of the Study:

  • To develop and validate a new spectroscopic method for determining the relative Lewis acidity of boranes.
  • To introduce *p*-fluorobenzonitrile (PFBN) as a 19F NMR probe for Lewis acid-base adducts.
  • To compare the new PFBN-based Lewis acidity scale with established methods and computational data.

Main Methods:

  • 19F Nuclear Magnetic Resonance (NMR) spectroscopy was employed using *p*-fluorobenzonitrile as the probe.
  • The chemical shift changes of PFBN upon adduct formation with various boranes were measured.
  • The resulting Lewis acidity scale was compared to the established Gutmann-Beckett scale (using 31P NMR) and computed fluoride affinities.

Main Results:

  • A reliable scale of relative Lewis acidities for a range of boranes was established using 19F NMR of PFBN.
  • The PFBN-based scale showed good correlation with the Gutmann-Beckett scale.
  • The experimental data exhibited strong agreement with computed fluoride affinities, validating the new method.

Conclusions:

  • *p*-Fluorobenzonitrile is an effective 19F NMR probe for quantifying borane Lewis acidity.
  • This method provides a complementary and potentially advantageous alternative to existing techniques.
  • The study validates the use of 19F NMR for Lewis acidity measurements in organometallic chemistry.