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Preparation of Amides01:29

Preparation of Amides

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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...
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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...
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Angle of Twist - Elastic Range01:13

Angle of Twist - Elastic Range

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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...
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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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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...
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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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.
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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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Magnetic Tweezers for the Measurement of Twist and Torque
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The Most Twisted Acyclic Amides: Structures and Reactivity.

Chengwei Liu1, Shicheng Shi1, Yongmei Liu1,2

  • 1Department of Chemistry , Rutgers University , 73 Warren Street , Newark , New Jersey 07102 , United States.

Organic Letters
|December 12, 2018
PubMed
Summary

Researchers synthesized highly twisted acyclic amides, mimicking transition states for peptide isomerization. These unique twisted amides disrupt orbital overlap, offering new insights into molecular configurations.

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Area of Science:

  • Organic Chemistry
  • Structural Chemistry
  • Computational Chemistry

Background:

  • Acyclic amides are fundamental in chemistry and biology.
  • Achieving significant twist in acyclic amides is challenging.
  • Understanding twisted conformations is crucial for studying reaction mechanisms.

Purpose of the Study:

  • To synthesize and characterize unprecedentedly twisted acyclic amides.
  • To investigate the structural and electronic properties of these twisted amides.
  • To explore their potential as mimics of transition states in peptide isomerization.

Main Methods:

  • Synthesis of substituted benzamides.
  • X-ray crystallography for structure determination.
  • Computational analysis of orbital overlap and geometry.

Main Results:

  • Achieved near-perpendicular twist (τ = 77°, N = Ac; τ = 87°, N = Boc) in N-substituted acyclic amides.
  • Observed disruption of nitrogen lone pair (Nlp) and carbonyl π* orbital overlap due to steric hindrance.
  • Demonstrated that these twisted amides serve as accessible transition state mimics for cis-trans peptide isomerization.

Conclusions:

  • The developed synthetic strategy enables access to highly twisted acyclic amides.
  • These compounds provide valuable models for understanding distorted amide geometries.
  • The findings offer new perspectives on peptide bond dynamics and isomerization processes.