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Related Experiment Videos

Bonding along a linear B...N...B triad.

Peter D Livant1, D John D Northcott, Yiping Shen

  • 1Department of Chemistry, Auburn University, Auburn, Alabama 36849-5312, USA. livanpd@auburn.edu

The Journal of Organic Chemistry
|September 25, 2004
PubMed
Summary
This summary is machine-generated.

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Tris(2,6-dihydroxyphenyl)amine diborate exhibits an unsymmetrical B-N-B bond, not a symmetrical three-center two-electron bond. A dynamic bond-switching equilibrium occurs in solution, involving solvent interactions.

Area of Science:

  • Inorganic Chemistry
  • Supramolecular Chemistry
  • Computational Chemistry

Background:

  • Three-center two-electron (3c-2e) bonds are fundamental in chemical bonding.
  • Understanding the stability and dynamics of such bonds is crucial for designing novel molecular architectures.
  • The B-N-B motif presents an interesting case for exploring linear bonding arrangements.

Purpose of the Study:

  • To synthesize and characterize tris(2,6-dihydroxyphenyl)amine diborate (4).
  • To investigate the nature of the B-N-B bonding in compound 4 using X-ray crystallography and NMR spectroscopy.
  • To elucidate the dynamic behavior and reaction mechanisms in solution and in the absence of solvent using computational methods.

Main Methods:

  • Synthesis of tris(2,6-dihydroxyphenyl)amine diborate.

Related Experiment Videos

  • X-ray crystal structure determination.
  • Temperature-dependent 13C NMR spectroscopy in THF solution.
  • Ab initio electronic structure calculations.

    • Main Results:

    • Compound 4 crystallizes with an unsymmetrical B-N-B array, featuring a 2c-2e B-N dative bond and solvent coordination to boron.
    • Solution NMR reveals a dynamic bond-switching equilibrium (DeltaG++ = 11.6 kcal/mol at 262 K) attributed to a "bell clapper" mechanism.
    • Computational studies indicate the bond switch proceeds via nucleophilic attack by THF, not a 3c-2e intermediate. The 3c-2e B...N...B form is a transition state in the solvent-free reaction.

    Conclusions:

    • The synthesized compound 4 does not exhibit a symmetrical 3c-2e B-N-B bond in the solid state.
    • The observed dynamic behavior in solution is driven by solvent-assisted bond switching.
    • The stability of three-center bonds against linear distortion is discussed in relation to the second-order Jahn-Teller effect.