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Related Concept Videos

Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.4K
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...
2.4K
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

2.2K
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
2.2K
Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

2.1K
The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
2.1K
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

3.2K
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...
3.2K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.9K
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...
2.9K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

2.8K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
2.8K

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Updated: Sep 22, 2025

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Polymerizing Base Sensitive Cyclic Carbonates Using Acid Catalysis.

Daniel J Coady1, Hans W Horn1, Gavin O Jones1

  • 1IBM, Almaden Research Center, 650 Harry Road, San Jose, California 95120, United States.

ACS Macro Letters
|May 18, 2022
PubMed
Summary
This summary is machine-generated.

Organic acids enable controlled polymerization of cyclic carbonates, even those with acidic protons. This acid catalysis mechanism involves dual activation, expanding monomer possibilities for advanced polymer synthesis.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Controlled ring-opening polymerization (ROP) is crucial for synthesizing polymers with defined properties.
  • Nitrogenous bases are common catalysts for cyclic carbonate ROP but are incompatible with acidic monomers.
  • Expanding the range of cyclic carbonate monomers is essential for developing new polymeric materials.

Purpose of the Study:

  • To investigate organic acids as catalysts for cyclic carbonate ROP.
  • To explore acid catalysis for monomers containing acidic protons.
  • To elucidate the mechanism of acid-catalyzed ROP.

Main Methods:

  • Computational molecular modeling was used to study the catalytic mechanism.
  • Experiments were designed to test acid compatibility with various cyclic carbonate monomers.
  • Polymerization kinetics and polymer properties were analyzed.

Main Results:

  • Organic acids were successfully employed to polymerize cyclic carbonates, including those with acidic protons.
  • Molecular modeling revealed a bifunctional activation pathway involving hydrogen bonding to monomer carbonyls and propagating hydroxyl groups.
  • Acid strength and conjugate base effects were identified as critical factors in catalysis.
  • Amide-containing monomers were polymerized under acid catalysis, yielding controlled polymer architectures.

Conclusions:

  • Acid catalysis offers a versatile alternative to base catalysis for cyclic carbonate ROP.
  • The dual activation mechanism explains the efficacy of acid catalysts.
  • This approach significantly broadens the scope of cyclic carbonate monomers for controlled polymerization, enabling the synthesis of novel functional polymers.