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Related Concept Videos

Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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 acid...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Acid-Catalyzed Hydration of Alkenes02:45

Acid-Catalyzed Hydration of Alkenes

Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.

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Quantitative SERS Detection of Uric Acid via Formation of Precise Plasmonic Nanojunctions within Aggregates of Gold Nanoparticles and Cucurbit[n]uril
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Cucurbituril-mediated supramolecular acid catalysis.

Cornelius Klöck1, Roy N Dsouza, Werner M Nau

  • 1School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, D-28759 Bremen, Germany.

Organic Letters
|May 26, 2009
PubMed
Summary

Cucurbiturils significantly accelerate acid hydrolysis reactions, with rate enhancements up to 300-fold observed for benzaldoxime. These macrocycles act as catalysts, promoting hydrolysis by encapsulating substrates.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Reaction Mechanisms
  • Host-Guest Chemistry

Background:

  • Cucurbiturils are macrocyclic hosts known for their ability to bind various guest molecules.
  • Acid hydrolysis is a fundamental organic reaction with broad applications.
  • Understanding host-guest interactions can reveal new catalytic pathways.

Purpose of the Study:

  • To investigate the effect of cucurbiturils on the rates of acid hydrolysis for specific substrates.
  • To determine the catalytic role of cucurbiturils in promoting acid hydrolysis.
  • To explore the mechanism of rate enhancement through guest encapsulation.

Main Methods:

  • Kinetic studies of acid hydrolysis for N-benzoyl-cadaverine, mono-N-(tert-butoxy)carbonyl cadaverine, and benzaldoxime.
  • Experiments conducted in the absence and presence of cucurbit[6]uril and cucurbit[7]uril.
  • Competitive inhibition studies using added cadaverine to probe the binding interactions.

Main Results:

  • Significant rate enhancements were observed for the acid hydrolysis of all investigated substrates in the presence of cucurbiturils.
  • Rate accelerations reached up to approximately 300-fold for the hydrolysis of benzaldoxime.
  • Competitive inhibition confirmed that cadaverine derivatives bind within the cucurbituril cavity, supporting the encapsulation mechanism.

Conclusions:

  • Cucurbiturils effectively promote acid hydrolysis reactions through host-guest complexation.
  • The observed rate enhancements demonstrate the catalytic potential of cucurbiturils in organic transformations.
  • Sub-stoichiometric amounts of macrocycles are sufficient, highlighting their efficiency as catalysts.