Related Experiment Video
Updated: May 12, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
EH3 (E = N, P, As) and H2 activation with N-heterocyclic silylene and germylene homologues
Marta Erminia Alberto1, Nino Russo, Emilia Sicilia
1Dipartimento di Chimica, Università della Calabria, 87036 Arcavacata di Rende (Cs), Italy.
Abstract:
DFT calculations have been used to probe the mechanism of the addition reaction of group 15 hydrides EH3 (E = N, P, As) and H2 to a N-heterocyclic silylene and its germylene homologue. Nitrogen lone pair donation into the vacant p-orbital of Si and Ge is the first step of ammonia activation, whereas silylene and germylene behave as nucleophiles toward dihydrogen, phosphane, and arsane. Formation of 1,4-addition products is kinetically favoured in all cases. In excess ammonia, the assistance of a second molecule drastically lowers the 1,1-addition energy barriers, enabling formation of 1,1-addition products. The participation of a second molecule in the P-H bond activation of phosphane also lowers the 1,1-addition energy barriers, but not enough to cause inversion.
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Basicity of Heterocyclic Aromatic Amines
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Five-Membered Heterocyclic Aromatic Compounds: Overview
