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

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 mi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-03, Vol.58 (12), p.4061-4064
Main Authors: Edel, Klara, Ishibashi, Jacob S. A., Liu, Shih‐Yuan, Bettinger, Holger F.
Format: Article
Language:English
Subjects:
1,2-azaborine
Adducts
Carbon monoxide
Lewis acid
Lewis acids
matrix isolation
Organic chemistry
Quantum chemistry
Xenon
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Summary: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. The BN analogue of ortho‐benzyne, 1,2‐azaborine, binds carbon monoxide and a xenon atom under matrix isolation conditions. The complexes with 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 computations at the MP2 level, and is similar to that of the Xe complex with the superelectrophilic carbene difluorovinylidene.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201813503