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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...
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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.

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Related Experiment Video

Updated: Jul 3, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

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Ester hydrolysis by a cyclodextrin dimer catalyst with a metallophenanthroline linking group.

Ying-Hua Zhou1, Meng Zhao, Zong-Wan Mao

  • 1MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 8, 2008
PubMed
Summary

A novel zinc complex with a beta-cyclodextrin dimer efficiently catalyzes ester hydrolysis. This catalyst shows significant rate enhancements, particularly for phosphate diesters, offering a promising new tool in catalysis.

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

Area of Science:

  • Supramolecular Chemistry
  • Catalysis
  • Coordination Chemistry

Background:

  • Beta-cyclodextrin dimers offer unique host-guest properties for molecular recognition and catalysis.
  • Zinc complexes are widely studied for their catalytic activity in hydrolysis reactions.
  • Developing efficient and selective catalysts for ester and phosphate diester hydrolysis remains a key challenge.

Purpose of the Study:

  • To synthesize and characterize a novel beta-cyclodextrin dimer, 1,10-phenanthroline-2,9-dimethyl-bridged-bis(6-monoammonio-beta-cyclodextrin) (phenBisCD, L).
  • To prepare and investigate the catalytic activity of its zinc complex (ZnL) for diester hydrolysis.
  • To elucidate the kinetic and mechanistic aspects of ZnL-catalyzed hydrolysis reactions.

Main Methods:

  • Synthesis and characterization of the phenBisCD ligand and its zinc complex (ZnL).
  • Potentiometric pH titration to determine complex formation and deprotonation constants.
  • Kinetic studies of bis(4-nitrophenyl) carbonate (BNPC), 4-nitrophenyl acetate (NA), and bis(4-nitrophenyl) phosphate (BNPP) hydrolysis.

Main Results:

  • The zinc complex ZnL was successfully synthesized and characterized.
  • ZnL exhibited highly efficient catalysis for BNPC hydrolysis (3.89x10(4)-fold rate enhancement) and moderate catalysis for NA hydrolysis (42-fold).
  • ZnL demonstrated significant catalytic activity for BNPP hydrolysis with a k(cat) of 9.9x10(-4) M(-1) s(-1), outperforming many other Zn(II) systems.

Conclusions:

  • The novel ZnL complex is a potent catalyst for the hydrolysis of various diesters, including phosphate diesters.
  • The catalytic activity is pH-dependent, with optimal performance observed at higher pH values.
  • The study proposes a plausible catalytic intermediate, offering insights into the reaction mechanism.