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Facile Energy Release from Substituted Dewar Isomers of 1,2‐Dihydro‐1,2‐Azaborinines Catalyzed by Coinage Metal Lewis Acids

Robert C. Richter, Sonja M. Biebl, Ralf Einholz, Johannes Walz, Cäcilia Maichle‐Mößmer, Markus Ströbele, Holger F. Bettinger, Ivana Fleischer

2024Angewandte Chemie International Edition22 citationsDOIOpen Access PDF

Abstract

Abstract Molecular solar thermal systems (MOST) represent an auspicious solution for the storage of solar energy. We report silver salts as a unique class of catalysts, capable of releasing the stored energy from the promising 1,2‐dihydro‐1,2‐azaborinine based MOST system. Mechanistic investigations provided insights into the silver catalyzed thermal backreaction, concurrently unveiling the first crystal structure of a 2‐aza‐3‐borabicyclo[2.2.0]hex‐5‐ene, the Dewar isomer of 1,2‐dihydro‐1,2‐azaborinine. Quantification of activation energies by kinetic experiments has elucidated the advantageous energy change associated with Lewis acid catalysts, a phenomenon corroborated through computational analysis. By means of low temperature NMR spectroscopy, mechanistic insights into the coordination of Ag + to the 1,2‐dihydro‐1,2‐azaborinine were gained.

Topics & Concepts

CatalysisLewis acids and basesChemistryMetalKinetic energyActivation energyCoordination complexThermalCombinatorial chemistryOrganic chemistryThermodynamicsQuantum mechanicsPhysicsMetal-Organic Frameworks: Synthesis and ApplicationsAsymmetric Hydrogenation and CatalysisN-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Facile Energy Release from Substituted Dewar Isomers of 1,2‐Dihydro‐1,2‐Azaborinines Catalyzed by Coinage Metal Lewis Acids | Litcius