Related Experiment Video
Updated: Mar 26, 2026
08:12
Generation of Zerovalent Metal Core Nanoparticles Using n-2-aminoethyl-3-aminosilanetriol
Published on: February 11, 2016
8.2K
A Triatomic Silicon(0) Cluster Stabilized by a Cyclic Alkyl(amino) Carbene
Kartik Chandra Mondal1, Sudipta Roy2, Birger Dittrich3
1Institut für Anorganische Chemie, Universität Göttingen, Tammannstrasse 4, 37077, Göttingen, Germany. csdkartik@iitm.ac.in.
Angewandte Chemie (International Ed. in English)
|January 30, 2016
Summary
Researchers synthesized a stable silicon(0) molecule, (cAAC)3Si3, using a carbene ligand. This novel triatomic silicon structure exhibits single bonds and was analyzed for its electronic properties.
Area of Science:
- Organosilicon Chemistry
- Main Group Element Chemistry
- Carbene Stabilization
Background:
- Neutral carbene adducts of silicon tetrachloride (SiCl4) are precursors to silicon compounds.
- Cyclic alkyl(amino)carbenes (cAAC) are effective ligands for stabilizing reactive species.
Purpose of the Study:
- To synthesize and characterize a novel carbene-stabilized triatomic silicon(0) molecule.
- To investigate the bonding, stability, and electronic properties of the synthesized silicon cluster.
Main Methods:
- Reduction of (cAAC)SiCl4 using potassium graphite.
- X-ray crystallography for structural determination.
- Quantum chemical calculations for electronic structure analysis.
Main Results:
- Stable (cAAC)3Si3, a silicon(0) molecule with a triangular arrangement of silicon atoms, was successfully synthesized.
- Si-Si bond lengths (2.399(8), 2.369(8), 2.398(8) Å) are consistent with Si-Si single bonds.
- Each silicon atom is trigonal pyramidal and possesses a lone pair of electrons.
Conclusions:
- The carbene ligand (cAAC) effectively stabilizes the unusual triatomic silicon(0) cluster.
- The molecule exhibits characteristics of single bonds, challenging previous assumptions about silicon cluster stability.
- Quantum chemical calculations provide insights into the bonding and electron distribution within the (cAAC)3Si3 molecule.
Related Concept Videos
02:38Electrophilic Addition to Alkynes: Halogenation
10.5K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
10.5K
02:10Carbocations
14.8K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
14.8K
02:45Alkyl Halides
21.9K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
21.9K
01:07Radicals: Electronic Structure and Geometry
5.4K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
5.4K
02:30Stability of Substituted Cyclohexanes
17.3K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
17.3K
01:22Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
2.4K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
2.4K