Related Experiment Video
Updated: May 17, 2026

Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
Published on: December 6, 2021
Reaction of an "invisible" frustrated N/B Lewis pair with dihydrogen
Sina Schwendemann1, Shunsuke Oishi, Susumu Saito
1Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, 48149 Münster, Germany.
Abstract:
D-(+)-Camphor forms the enamine 2 with piperidine. Compound 2 adds HB(C(6)F(5))(2) at the enamine carbon atom C3 to form a Lewis acid/Lewis base adduct (exo-/endo-isomers of 3). Exposure of 3 to dihydrogen (2.5 bar, room temperature) leads to heterolytic splitting of H(2) to form the H(+)/H(-) addition products (4, two diastereoisomers) of the "invisible" frustrated Lewis pairs (5, two diastereoisomers) that were apparently generated in situ by enamine hydroboration under equilibrium conditions.
Related Concept Videos
Covalent Bonding and Lewis Structures
Lewis Acids and Bases
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
Lewis Acids and Bases
Exceptions to the Octet Rule
Chain Reactions
Lewis Symbols and the Octet Rule

