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Preparation of Amides01:29

Preparation of Amides

4.1K
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...
4.1K
Angle of Twist: Problem Solving01:13

Angle of Twist: Problem Solving

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An electric motor applies a torque of 700 N·m to an aluminum shaft, triggering a stable rotation. Two pulleys, B and C, are subjected to torques of 300 N·m and 400 N·m, respectively. The modulus of rigidity is provided as 25 GPa. With the knowledge of the length and diameter of each segment, the twist angle between the two pulleys can be computed. First, a section cut is made between pulleys B and C, and the cut cross-section is analyzed using a free-body diagram. Given that the torque...
811
Angle of Twist - Elastic Range01:13

Angle of Twist - Elastic Range

827
Consider a cylindrical shaft with a length denoted by L and a consistent cross-sectional radius referred to as r. This shaft undergoes a torque at the free end. The highest shearing strain within the shaft is directly proportional to the twist angle and the radial distance from the shaft axis. When the shaft behaves elastically, this shearing strain can be articulated using variables such as the applied torque, radial distance, the polar moment of inertia, and the modulus of rigidity. By...
827
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.5K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
4.5K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.5K
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...
3.5K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.4K
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...
4.4K

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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The Most Twisted Amide: Structure and Reactions.

Anthony J Kirby1, Igor V Komarov1, Peter D Wothers1

  • 1University Chemical Laboratory, Cambridge CB2 1EW (UK), Fax: (+44) 1223-336-362.

Angewandte Chemie (International Ed. in English)
|May 2, 2018
PubMed
Summary

This study reveals that amide 1 exhibits ketone-like behavior due to its twisted structure. Its crystal structure shows a pyramidal nitrogen and a planar carbonyl group, challenging typical amide characteristics.

Keywords:
AmidesCage compoundsKetonesStereoelectronic effects

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Amides typically possess a planar structure due to resonance.
  • Twisted amide conformations are less common and their properties are not fully understood.

Purpose of the Study:

  • To investigate the structural and electronic properties of a highly twisted amide (amide 1).
  • To compare the behavior of amide 1 with typical amides and ketones.

Main Methods:

  • X-ray crystallography was used to determine the crystal structure of amide 1.
  • Spectroscopic and computational methods were employed to analyze its electronic properties.

Main Results:

  • The crystal structure of amide 1 revealed a 90° twist between the amide bond.
  • The nitrogen atom was found to be pyramidal, deviating from planarity.
  • The carbonyl group remained planar, similar to ketones.

Conclusions:

  • Amide 1 displays characteristics more akin to a ketone than a typical amide.
  • The pyramidal nitrogen and planar carbonyl group contribute to its unusual chemical behavior.