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Preparation of Amides01:29

Preparation of Amides

3.2K
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...
3.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.6K
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...
3.6K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

9.5K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal,...
9.5K
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
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.1K
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

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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A predictive journey towards trans-thioamides/amides.

Michele Tomasini1,2, Jin Zhang3, Hui Zhao3

  • 1Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, C/Maria Aurèlia Capmany 69, 17003, Girona, Catalonia, Spain. albert.poater@udg.edu.

Chemical Communications (Cambridge, England)
|August 19, 2022
PubMed
Summary
This summary is machine-generated.

Predictive chemistry guides the selection of substituents on (thio)amides to favor the trans isomer. Experimental validation confirmed the synthesis of a trans-isomer candidate, bridging computational and organic chemistry.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Physical Chemistry

Background:

  • The cis-trans isomerization of (thio)amides is crucial in various chemical processes.
  • Understanding the conformational preferences of (thio)amides is essential for designing molecules with specific properties.

Purpose of the Study:

  • To develop a predictive model for controlling the cis-trans isomerization of (thio)amides.
  • To identify key structural factors influencing the preference for cis or trans conformations.
  • To guide the rational design of substituents for achieving higher yields of the trans isomer.

Main Methods:

  • Density Functional Theory (DFT) calculations were employed to model the isomerization process.
  • Multilinear analysis and cross-validation were used to identify significant parameters affecting energy barriers and isomer stability.
  • Experimental synthesis was performed to validate the computational predictions.

Main Results:

  • A predictive model was established for the cis-trans isomerization of (thio)amides.
  • Key parameters influencing the energy barriers and relative stability of cis and trans isomers were identified.
  • The synthesis of a sterically hindered trans isomer, featuring t-butyl substituents, was successfully achieved.

Conclusions:

  • Predictive chemistry, integrating computational and experimental approaches, effectively guides the synthesis of specific isomers.
  • The study demonstrates a method for controlling the stereochemical outcome of (thio)amide isomerization.
  • This work provides a foundation for the targeted synthesis of molecules with desired conformational preferences.