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Lewis Acids and Bases02:16

Lewis Acids and Bases

15.2K
This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...
15.2K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

10.1K

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.
10.1K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Ladder Diagrams: Complexation Equilibria01:07

Ladder Diagrams: Complexation Equilibria

431
Ladder diagrams are useful for evaluating equilibria involving metal-ligand complexes. The vertical scale of the ladder diagram represents the concentration of unreacted or free ligand, pL. The horizontal lines on the scale depict the log of stepwise formation constants for metal-ligand complexes and indicate the dominant species in all the regions.
The formation constant, K1, for the formation of Cd(NH3)2+ complex from cadmium and ammonia is 3.55 × 102. Log K1 (i.e. pNH3) is 2.55, and...
431
Relative Reactivity of Carboxylic Acid Derivatives01:13

Relative Reactivity of Carboxylic Acid Derivatives

3.0K
Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of reactivity.
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
Halide ions < Acyloxy ions < Alkoxy ions < Amine ions
3.0K

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Updated: Sep 25, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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Zinc Ammonio-dodecaborates: Synthesis, Lewis Acid Strength, and Reactivity.

Rudolf J Wehmschulte1, Brittany Bayliss1, Sydney Reed1

  • 1Chemistry Program, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901, United States.

Inorganic Chemistry
|April 26, 2022
PubMed
Summary

New zinc catalysts with chlorinated ammonio-closo-dodecaborate anions were synthesized. These catalysts showed low activity in 1-hexene hydrosilylation but moderate activity for benzophenone and acetophenone hydrosilylation.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Boron Chemistry

Background:

  • Zinc salts with weakly coordinating anions are explored as catalysts.
  • Ammonio-closo-dodecaborate anions offer alternatives to carborate anions.
  • Understanding anion basicity and Lewis acidity is crucial for catalyst design.

Purpose of the Study:

  • To synthesize and characterize zinc salts with novel chlorinated ammonio-closo-dodecaborate anions.
  • To investigate the catalytic activity of these zinc complexes in hydrosilylation reactions.
  • To correlate catalyst performance with anion properties like basicity and fluoride ion affinity.

Main Methods:

  • Synthesis of zinc salts ([EtZn][A] and Zn[A]2) with various chlorinated ammonio-dodecaborate anions.
  • Evaluation of catalytic activity in the hydrosilylation of 1-hexene, benzophenone, and acetophenone.
  • Determination of anion basicity and fluoride ion affinities (FIAs) of the zinc complexes.

Main Results:

  • Zinc salts with [Me3NB12Cl11]-, [Pr3NB12H5Cl6]-, [Bu3NB12H4Cl7]-, and [Hex3NB12H5Cl6]- anions were successfully prepared.
  • Anion [Hex3NB12H5Cl6]- exhibits basicity similar to triflimide.
  • Fluoride ion affinities of [EtZn][Pr3NB12H5Cl6] and Zn[Pr3NB12H5Cl6]2 are lower than established Lewis acids.
  • Catalytic activity was low for 1-hexene hydrosilylation and moderate for benzophenone and acetophenone hydrosilylation.

Conclusions:

  • Higher anion basicity and lower Lewis acidity of zinc centers correlate with reduced catalytic activity.
  • Chlorinated ammonio-closo-dodecaborate anions present tunable properties for catalyst development.
  • The investigated zinc catalysts show potential but require further optimization for efficient hydrosilylation.