Related Experiment Video
Updated: Aug 2, 2025
A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
One silicon atom of bis(silylene) functions as a selective Lewis base under adduct formation with a Lewis acid
Yi Ding1,2, Mohd Nazish2, Paul Niklas Ruth2
1College of Chemistry and Chemical Engineering, State Key Laboratory of High-Efficiency Utilization of Coal and Green Chemical Engineering, Ningxia University, Yinchuan 750021, China. yiding@nxu.edu.cn.
Abstract:
Herein, we describe the facile and selective one-pot synthetic route to silylene-aluminum and silylene-gallium adducts. Reduction of silylene LSiCl (L = PhC(NBu)2) with KC8 in the presence of bulky and sterically hindered cyclopentadienyl aluminum Cp'''AlCl2 (Cp''' = 1,2,4-Bu3C5H2) and gallium [η1-Cp'''Ga(μ-Cl)Cl]2 to afford the Lewis acid-base adducts η1-Cp'''M(Cl2) ← Si(L)-SiL (M = Al, 1; M = Ga, 3). To confirm the formation of the Lewis acid-base adduct, the bis(silylene) LSi(I)-Si(I)L reacts with Cp'''AlI2 to form η1-Cp'''Al(I2) ← Si(L)-SiL (2). These are the first examples where one Si atom in the bis(silylene) is a Lewis base and coordinates with aluminum or gallium to form a Lewis acid-base adduct, while the other Si atom in the bis(silylene) still maintains the characteristics of silylene. Compound 3 was heated to 70 °C in toluene for 4 hours and decomposed into the silylene LSiCl and Cp'''GaI. Compounds 1-3 are well characterized with NMR spectroscopic methods and single-crystal X-ray structural analysis.
More Related Videos
08:48Selective Area Modification of Silicon Surface Wettability by Pulsed UV Laser Irradiation in Liquid Environment
Published on: November 9, 2015
08:02Rendering SiO2/Si Surfaces Omniphobic by Carving Gas-Entrapping Microtextures Comprising Reentrant and Doubly Reentrant Cavities or Pillars
Published on: February 11, 2020
Related Concept Videos
02:33Lewis 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...
02:42Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
02:54Lewis Structures of Molecular Compounds and Polyatomic Ions
02:26Preparation and Reactions of Sulfides
02:38Electrophilic Addition to Alkynes: Halogenation
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.
01:14Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene