The Lightest Element Phosphoranylidene: NHC-Supported Cyclic Borylidene–Phosphorane with Significant B=P Character
Dr. Alfredo Rosas-Sánchez
Université de Toulouse, UPS, CNRS, LHFA UMR 5069, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorDr. Isabel Alvarado-Beltran
Université de Toulouse, UPS, CNRS, LHFA UMR 5069, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorCorresponding Author
Dr. Antoine Baceiredo
Université de Toulouse, UPS, CNRS, LHFA UMR 5069, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorDr. Daisuke Hashizume
Materials Characterization Support Unit, RIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorDr. Nathalie Saffon-Merceron
Université de Toulouse, UPS, CNRS, ICT FR2599, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorProf. Vicenç Branchadell
Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain
Search for more papers by this authorCorresponding Author
Dr. Tsuyoshi Kato
Université de Toulouse, UPS, CNRS, LHFA UMR 5069, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorDr. Alfredo Rosas-Sánchez
Université de Toulouse, UPS, CNRS, LHFA UMR 5069, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorDr. Isabel Alvarado-Beltran
Université de Toulouse, UPS, CNRS, LHFA UMR 5069, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorCorresponding Author
Dr. Antoine Baceiredo
Université de Toulouse, UPS, CNRS, LHFA UMR 5069, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorDr. Daisuke Hashizume
Materials Characterization Support Unit, RIKEN Center for Emergent Matter Science (CEMS), 2-1 Hirosawa, Wako, Saitama, 351-0198 Japan
Search for more papers by this authorDr. Nathalie Saffon-Merceron
Université de Toulouse, UPS, CNRS, ICT FR2599, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorProf. Vicenç Branchadell
Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain
Search for more papers by this authorCorresponding Author
Dr. Tsuyoshi Kato
Université de Toulouse, UPS, CNRS, LHFA UMR 5069, 118 route de Narbonne, 31062 Toulouse, France
Search for more papers by this authorGraphical Abstract
Opposites attract: A phosphorus bora-ylide stabilized by an N-heterocyclic carbene ligand was synthesized. Experimental electron density analysis and DFT calculations indicate enhanced phosphorane character (rather than ylide character) with an exceptionally strong B→P π-back bonding compared to related compounds; this is due to the electronegativity difference between boron and phosphorus atoms.
Abstract
A borylidene–phosphorane, the lightest phosphoranylidene, which is stabilized by an N-heterocyclic carbene ligand, was synthesized and fully characterized. Experimental electron density analysis and DFT calculations indicate an enhanced ylene character (rather than an ylide character) with an exceptionally strong B→P π-back bonding related to the less electronegative boron compared to phosphorus.
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