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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.3K
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

4.0K
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 Amides01:29

Preparation of Amides

3.8K
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...
3.8K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.4K
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...
4.4K
Anticholinesterase Agents: Poisoning and Treatment01:26

Anticholinesterase Agents: Poisoning and Treatment

1.4K
Anticholinesterases, also known as cholinesterase inhibitors, work by blocking the breakdown of acetylcholine, leading to its accumulation in the synaptic cleft. This accumulation indirectly enhances both muscarinic and nicotinic actions. These agents are classified as reversible or irreversible based on their mechanism of action.     
Irreversible agents form a strong bond with the cholinesterase enzyme, making it inactive. The breakdown of the phosphorylated enzyme is...
1.4K
Physical Properties of Amines01:26

Physical Properties of Amines

4.0K
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
4.0K

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Related Experiment Videos

Acetamidoxime.

Marilyn M Olmstead1, Javad J Sahbari

  • 1Department of Chemistry, University of California, Davis, CA 95616, USA. olmstead@indigo.ucdavis.edu

Acta Crystallographica. Section C, Crystal Structure Communications
|December 13, 2003
PubMed
Summary
This summary is machine-generated.

N-hydroxyethanimidamide, the oxime of acetamide, exhibits a complex crystal structure with strong and weak hydrogen bonds. Conjugation influences its molecular geometry, resulting in unusual bond distances and angles.

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Area of Science:

  • Crystal engineering
  • Molecular structure
  • Hydrogen bonding

Background:

  • Acetamide oxime (N-hydroxyethanimidamide) is a molecule with potential applications in various chemical fields.
  • Understanding its solid-state structure is crucial for predicting its chemical behavior and designing new materials.

Purpose of the Study:

  • To elucidate the intricate hydrogen-bonding network in the crystal structure of N-hydroxyethanimidamide.
  • To investigate the influence of conjugation on the molecular geometry, including bond distances and angles.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of intermolecular interactions, specifically hydrogen bonds, was performed.

Main Results:

  • A complex hydrogen-bonding arrangement was identified, featuring one strong O-H...N interaction.
  • Weaker hydrogen bonds involving amide groups were also observed.
  • Conjugation effects were found to cause atypical bond distances and angles within the molecule.

Conclusions:

  • The crystal structure of N-hydroxyethanimidamide is characterized by a sophisticated hydrogen-bonding network.
  • Molecular geometry is significantly influenced by conjugation, leading to non-standard structural parameters.
  • These findings provide fundamental insights into the solid-state properties of acetamide oxime.