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Related Concept Videos

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

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

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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...
2.1K
Preparation of Amides01:29

Preparation of Amides

3.4K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.4K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

7.6K
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...
7.6K
Urea Cycle01:23

Urea Cycle

44.1K
The urea cycle describes how liver cells convert ammonia to urea. Ammonia is a toxic waste product of protein catabolism. Land animals must convert ammonia into the less toxic urea which can be safely eliminated by the kidneys through urine. Marine animals excrete ammonia directly, and the surrounding water dilutes the ammonia to safe levels.
44.1K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

5.4K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
5.4K

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Supramolecular assembly in a Janus-type urea system.

Gareth O Lloyd1, Jonathan W Steed

  • 1Institute of Chemical Sciences, School of Engineering and Physical Sciences, William Perkin Building, Heriot-Watt University, Edinburgh, EH14 4AS, Scotland, UK. g.o.lloyd@hw.ac.uk.

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A pyrazolyl urea ligand shows two conformations. Metal coordination favors an outward form, leading to anion binding or self-assembly into solution-stable supramolecular structures like hexameric barrels.

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Area of Science:

  • Supramolecular Chemistry
  • Coordination Chemistry
  • Organic Ligand Design

Background:

  • Pyrazolyl urea ligands are versatile building blocks in supramolecular chemistry.
  • Ligand conformation plays a critical role in directing self-assembly and host-guest interactions.
  • Understanding metal-ligand interactions is key to designing functional supramolecular architectures.

Purpose of the Study:

  • To investigate the conformational behavior of a pyrazolyl urea ligand.
  • To explore the impact of metal coordination on ligand conformation and assembly.
  • To characterize the resulting supramolecular structures formed in solution.

Main Methods:

  • Synthesis and characterization of the pyrazolyl urea ligand.
  • X-ray crystallography to determine solid-state structures.
  • Solution-state studies (e.g., NMR, UV-Vis) to probe conformation and assembly.

Main Results:

  • The pyrazolyl urea ligand exists in two distinct conformations: outward and inward-facing NH groups.
  • Metal coordination selectively enforces the outward conformation.
  • This outward conformation facilitates either anion complexation or self-association into extended supramolecular assemblies.
  • A stable hexameric barrel structure was observed and persisted in solution.

Conclusions:

  • Metal coordination is a powerful tool to control ligand conformation and drive the formation of specific supramolecular architectures.
  • The identified pyrazolyl urea ligand can act as a platform for anion recognition or the construction of robust, solution-phase supramolecular structures.
  • The hexameric barrel represents a stable supramolecular entity with potential applications in molecular recognition or encapsulation.