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Related Concept Videos

Lewis Acids and Bases02:16

Lewis Acids and Bases

14.2K
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...
14.2K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.8K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
2.8K
Molecular Structure and Acidity02:34

Molecular Structure and Acidity

17.4K
An acid can be deprotonated to form a conjugate base or an anion. If the produced anion is more stable, then the acid is stronger. On the contrary, if the anion is unstable, then the acid is weaker. Hence, to determine the acidity of the compound, the stability of its conjugate base is studied using various factors.
The size effect explains the change in atomic size on acidity. When comparing the acids formed from elements that belong to the same column in the periodic table, their atomic sizes...
17.4K
Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

7.1K
Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
7.1K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.9K

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.
9.9K
Polyprotic Acids03:38

Polyprotic Acids

29.3K
Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
29.3K

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Updated: Aug 6, 2025

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

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Cationic Triarylchlorostibonium Lewis Acids.

Omar Coughlin1, Tobias Krämer2, Sophie L Benjamin1

  • 1Department of Chemistry, Nottingham Trent University, Clifton Lane, Nottingham NG11 8NS, U.K.

Organometallics
|March 20, 2023
PubMed
Summary
This summary is machine-generated.

New organopnictogen Lewis acid catalysts, specifically triarylchlorostibonium salts, demonstrate tunable acidity based on fluorination. These compounds show catalytic activity in dimerization and Friedel-Crafts reactions.

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Last Updated: Aug 6, 2025

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Area of Science:

  • Organometallic Chemistry
  • Main-Group Catalysis
  • Lewis Acid Chemistry

Background:

  • Organopnictogen cations are emerging as potent main-group Lewis acid catalysts.
  • Weakly coordinated cations offer tunable reactivity for catalytic applications.

Purpose of the Study:

  • To synthesize and characterize a series of triarylchlorostibonium salts with varying aryl substituents.
  • To investigate the structural, electronic, and reactivity properties of these novel Lewis acids.
  • To evaluate their potential as catalysts in organic transformations.

Main Methods:

  • Synthesis and structural determination (X-ray crystallography) of triarylchlorostibonium salts.
  • Computational modeling (DFT) to understand electronic properties and reaction mechanisms.
  • Reactivity studies including catalytic dimerization and Friedel-Crafts alkylation.

Main Results:

  • A series of [Ar3SbCl][B(C6F5)4] salts were successfully synthesized and characterized.
  • Lewis acidity of the [Ar3SbCl]+ cation increases with aryl ring fluorination, with para-fluorination showing a quenching effect.
  • The compounds exhibited catalytic activity in 1,1-diphenylethylene dimerization and benzene Friedel-Crafts alkylation.
  • Computational studies elucidated the reduction mechanism of the cation to Ar3Sb via Et3SiH.

Conclusions:

  • Triarylchlorostibonium salts are effective Lewis acid catalysts with tunable acidity.
  • Fluorination of aryl substituents is a key strategy for modulating catalytic activity.
  • These compounds represent a promising class of catalysts for various organic reactions.