Superelectrophilicity of 1,2-Azaborine: Formation of Xenon and Carbon Monoxide Adducts

Angew Chem Int Ed Engl. 2019 Mar 18;58(12):4061-4064. doi: 10.1002/anie.201813503. Epub 2019 Feb 20.

Abstract

The BN analogue of ortho-benzyne, 1,2-azaborine, is shown to bind carbon monoxide and a xenon atom under matrix isolation conditions, demonstrating its strongly Lewis acidic superelectrophilic nature. The Lewis acid-base complexes involving CO and Xe can be cleaved photochemically and reformed by mildly annealing the matrices. The interaction energy of 1,2-azaborine with Xe is 3 kcal mol-1 according to quantum chemical computations, and is similar to that of the superelectrophilic carbene difluorovinylidene.

Keywords: 1,2-azaborine; Lewis acids; carbon monoxide; matrix isolation; xenon.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry
  • Boron Compounds / chemistry*
  • Carbon Monoxide / chemistry*
  • Cycloaddition Reaction
  • Lewis Bases / chemistry
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Quantum Theory
  • Xenon / chemistry*

Substances

  • 1,2-azaborine
  • Benzene Derivatives
  • Boron Compounds
  • Lewis Bases
  • benzyne
  • carbene
  • Xenon
  • Carbon Monoxide
  • Methane