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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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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.
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Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

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A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

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

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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.
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Effect of morpholine, and 4-methylmorpholine on urethane formation: a computational study.

Hadeer Q Waleed1,2, Rachid Hadjadj1,2, Béla Viskolcz1,2

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This study explores urethane formation using computational methods. 4-methylmorpholine is a more effective catalyst than morpholine for this reaction, offering insights into polyurethane catalyst design.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Catalysis

Background:

  • Urethane formation is crucial for polyurethane synthesis.
  • Amine catalysts play a significant role in accelerating this reaction.
  • Understanding reaction mechanisms is key to catalyst optimization.

Purpose of the Study:

  • To theoretically investigate urethane formation from phenyl isocyanate and butan-1-ol.
  • To compare the catalytic efficiency of morpholine and 4-methylmorpholine.
  • To elucidate the reaction mechanism with and without amine catalysts.

Main Methods:

  • Density Functional Theory (DFT) calculations at BHandHLYP/6-31G(d) and G3MP2BHandHLYP levels.
  • Geometry optimization and thermodynamic property calculations.
  • Analysis of reaction pathways and intermediate structures, including a correction for zwitterionic intermediates.

Main Results:

  • The catalytic mechanism involves seven steps, differing significantly from the catalyst-free pathway.
  • Calculated reactant complexes show high similarity to literature crystal structures, validating the proposed mechanism.
  • 4-methylmorpholine demonstrates higher catalytic activity than morpholine, attributed to differences in proton affinity (PA).

Conclusions:

  • Amine catalysts, particularly 4-methylmorpholine, are effective in urethane synthesis.
  • The findings provide valuable insights for the design and development of polyurethane catalysts.
  • Theoretical studies are crucial for understanding and optimizing chemical reaction pathways.