Related Experiment Video
Updated: Sep 5, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
A Fluoroponytailed NHC-Silver Complex Formed from Vinylimidazolium/AgNO3 under Aqueous-Ammoniacal Conditions
Gabriel Partl1, Marcus Rauter2, Lukas Fliri3
1Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, CCB, Innrain 80-82, 6020 Innsbruck, Austria.
Abstract:
3-(1H,1H,2H,2H-Perfluorooctyl)-1-vinylimidazolium chloride [2126844-17-3], a strong fluorosurfactant with remarkably high solubility in water, was expediently converted into the respective doubly NHC-complexed silver salt with nitrate as counter ion in quantitative yield. Due to its vinyl substituents, [bis(3-(1H,1H,2H,2H-perfluorooctyl)-1-vinylimidazol-2-ylidene)silver(I)] nitrate, Ag(FNHC), represents a polymerizable N-heterocyclic carbene transfer reagent, thus potentially offering simple and robust access to coordination polymers with crosslinking metal bridges. The compound was characterized by infrared and NMR spectroscopy, mass spectrometry as well as elemental analysis, and supplemented by X-ray single-crystal structure determination. It crystallizes in the monoclinic crystal system in the space group P21/c. With 173.3°, the geometry of the Ag-carbene bridge deviates slightly from linearity. The disordered perfluoroalkyl side chains exhibit a helical conformation.
More Related Videos
Related Concept Videos
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Formation of Complex Ions
Diazonium Group Substitution: –OH and –H
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...

