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Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

10.0K

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.
10.0K
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

3.3K
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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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...
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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.3K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.3K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.1K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.1K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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Rational Design of Cationic Silyl Lewis Acids.

Corinna Girschik1, Saskia Rathjen1, Lina Möllmann1

  • 1Institute of Chemistry, Carl von Ossietzky Universität Oldenburg, Carl von Ossietzky-Str. 9-11, Oldenburg, D-26129, Federal Republic of Germany, European Union.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 3, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel cationic silyl Lewis acids using naphthalene or acenaphthalene scaffolds. These compounds exhibit tunable Lewis acidity, with some exceeding the strength of tris(pentafluorophenyl)borane (BCF).

Keywords:
Lewis acidityNMRseleniumsiliconsilyl cation

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Area of Science:

  • Organosilicon Chemistry
  • Lewis Acid Catalysis
  • Supramolecular Chemistry

Background:

  • Cationic silyl Lewis acids are crucial in catalysis, but their acidity tuning remains a challenge.
  • Stabilization of silicon centers with donor groups is key to modulating Lewis acidity.
  • Naphthalene and acenaphthalene scaffolds offer unique structural platforms for Lewis acid design.

Purpose of the Study:

  • To synthesize and characterize novel selanyl-stabilized cationic silyl Lewis acids.
  • To investigate the impact of structural modifications on Lewis acid strength.
  • To evaluate the efficacy of the p-fluorobenzonitrile (FBN) method for assessing Lewis acidity.

Main Methods:

  • Synthesis of silyl Lewis acids incorporating naphthalene or acenaphthalene backbones.
  • Evaluation of Lewis acid strength using the p-fluorobenzonitrile (FBN) complexation method.
  • Structural characterization via X-ray crystallography and nuclear magnetic resonance (NMR) spectroscopy.

Main Results:

  • A series of selanyl-stabilized cationic silyl Lewis acids were successfully synthesized.
  • Lewis acidity was tunable, with some compounds demonstrating greater strength than tris(pentafluorophenyl)borane (BCF).
  • Structural studies confirmed silicon penta-coordination in a cationic FBN complex.

Conclusions:

  • Structural modifications significantly influence the Lewis acidity of silyl Lewis acids.
  • The FBN method is a reliable tool for quantifying subtle differences in Lewis acid strength.
  • These findings open avenues for designing highly potent Lewis acid catalysts.