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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.4K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.5K
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...
3.5K
Structure of Amines01:19

Structure of Amines

2.5K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
2.5K
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

2.0K
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
2.0K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

2.8K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Updated: Jun 28, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Simultaneous switching of two different CO2-switchable amines in the same solution.

Matthew Sanger1, Daniel Barker1, Philip G Jessop1

  • 1Department of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, Canada K7L 2S8. jessop@queensu.ca.

Physical Chemistry Chemical Physics : PCCP
|April 9, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a model to predict the pH and protonation of two different bases in CO2-responsive systems. Simultaneous switching of two CO2-switchable amines is possible within specific concentration and basicity ranges.

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Area of Science:

  • Chemistry
  • Materials Science
  • Chemical Engineering

Background:

  • CO2-responsive materials utilize bases that protonate/deprotonate in response to CO2 presence.
  • Existing research focuses on single-base systems, limiting the complexity of CO2-switchable materials.
  • Understanding interactions in multi-base systems is crucial for advanced material design.

Purpose of the Study:

  • To develop a predictive model for solution pH and base protonation in systems with two different bases under varying CO2 conditions.
  • To experimentally validate the model by demonstrating and analyzing the simultaneous switching of two distinct CO2-switchable amines.
  • To establish criteria for successful simultaneous switching of multiple bases in CO2-responsive systems.

Main Methods:

  • Development of a predictive model for solution pH and % protonation of two bases.
  • Experimental investigation of two different CO2-switchable amines in solution.
  • Analysis of amine concentrations, basicities, and pKaH values to determine switching feasibility.

Main Results:

  • The predictive model accurately forecasts solution pH and protonation levels for dual-base systems.
  • Simultaneous switching of two CO2-switchable amines was experimentally achieved.
  • Successful switching requires specific concentration and basicity ranges, with pKaH values differing by no more than 3 units.

Conclusions:

  • A predictive model enables the design of complex CO2-responsive systems with multiple bases.
  • The simultaneous switching of two CO2-switchable amines is feasible under defined conditions.
  • This research advances the development of sophisticated CO2-capture and responsive materials.