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Related Concept Videos

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...
3.1K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.8K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.8K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

6.4K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
6.4K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.7K
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...
2.7K
Structure of Amines01:19

Structure of Amines

2.7K
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’...
2.7K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.1K
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.
3.1K

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Light-Driven Crystallization-Induced Dynamic Resolution of Amines.

Jonathan M Meinhardt1, Diane D Kim1, Emily J Wu1

  • 1Department of Chemistry, Princeton University; Princeton, New Jersey 08544, United States.

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|July 14, 2025
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Summary
This summary is machine-generated.

This study introduces a new method for separating chiral amine enantiomers using photoredox catalysis and crystallization. This approach efficiently resolves racemic amines, producing high yields of specific enantiomers for chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Catalysis

Background:

  • Chiral amines are crucial building blocks in pharmaceuticals and fine chemicals.
  • Efficient methods for enantiomeric resolution of racemic amines are highly sought after.
  • Existing methods can be limited by harsh conditions or low yields.

Purpose of the Study:

  • To develop a novel, mild, and efficient method for the dynamic resolution of racemic amines.
  • To couple catalytic photoredox-mediated racemization with in situ diastereomeric crystallization.
  • To provide a streamlined approach for accessing enantiomerically pure α-chiral amines.

Main Methods:

  • Utilizing an iridium chromophore and an achiral thiol cocatalyst for photoredox-mediated racemization.
  • Employing in situ diastereomeric salt formation with chiral resolving acids.
  • Applying the method to various secondary and tertiary amine structures.

Main Results:

  • Successful dynamic resolution of racemic amines under mild, redox-neutral conditions.
  • High yields and enantioselectivities achieved for diverse amine families.
  • Demonstrated utility across secondary and tertiary α-chiral amines.

Conclusions:

  • The developed method offers an effective strategy for the dynamic resolution of amines.
  • This approach simplifies the preparation of valuable chiral amine compounds.
  • Potential for broad application in fine chemical synthesis and pharmaceutical development.