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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Published on: April 19, 2019

Abnormal carbene-silicon halide complexes.

Yuzhong Wang¹, Yaoming Xie, Pingrong Wei

¹Department of Chemistry, The University of Georgia, Athens, Georgia 30602-2556, USA. robinson@uga.edu.

Dalton Transactions (Cambridge, England : 2003)

|November 26, 2015

Summary

This summary is machine-generated.

Researchers synthesized novel N-heterocyclic carbene (NHC) complexes by reacting an anionic NHC with silicon tetrachloride. These complexes offer new pathways for creating silicon-substituted carbene compounds and cationic species.

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Probing C84-embedded Si Substrate Using Scanning Probe Microscopy and Molecular Dynamics

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Published on: September 28, 2016

Area of Science:

Organometallic Chemistry
Silicon Chemistry
Carbene Chemistry

Background:

N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
Silicon tetrachloride (SiCl4) is a common reagent for introducing silicon functionalities.
Understanding the reactivity of anionic NHCs with electrophiles is crucial for developing new synthetic methodologies.

Purpose of the Study:

To investigate the reaction of an anionic N-heterocyclic dicarbene (NHDC) with silicon tetrachloride.
To synthesize and characterize novel silicon-substituted NHC complexes.
To explore the formation of abnormal carbene complexes and cationic silicon species.

Main Methods:

Synthesis of an anionic NHDC precursor.
Reaction of the NHDC with SiCl4 to form a trichlorosilyl-substituted NHC complex.
Conversion to an abnormal carbene-SiCl4 complex using HCl·NEt3.
Reaction with CH2Cl2 to yield a cationic SiCl3+ complex.
Characterization using spectroscopic methods and Density Functional Theory (DFT) computations.

Main Results:

The anionic NHDC reacted with SiCl4 to yield a trichlorosilyl-substituted NHC complex (7).
Complex 7 was converted to an abnormal carbene-SiCl4 complex (8) upon treatment with HCl·NEt3.
Complex 7 reacted with CH2Cl2 to form an abnormal carbene-complexed SiCl3+ cation (9).
DFT computations were employed to investigate the bonding nature in complex 9.

Conclusions:

Novel silicon-substituted NHC complexes and abnormal carbene complexes were successfully synthesized.
The study demonstrates a new route to functionalized NHCs and cationic silicon species.
DFT calculations provide insights into the electronic structure and bonding of the novel cationic complex.