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Related Concept Videos

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.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
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Preparation of Amides01:29

Preparation of Amides

3.0K
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...
3.0K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

4.5K
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.
4.5K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

2.7K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
2.7K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

3.1K
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
3.1K
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

5.4K
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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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Theoretical and Experimental Study on Carbodiimide Formation.

Marcell Dániel Csécsi1,2, Virág Kondor1, Edina Reizer1

  • 1Institute of Chemistry, University of Miskolc, H-3515 Miskolc, Hungary.

International Journal of Molecular Sciences
|July 27, 2024
PubMed
Summary

Researchers investigated diphenylcarbodiimide (CDI) formation from phenyl isocyanate using a phosphorus catalyst. Computational and experimental data revealed a detailed mechanism and an activation energy of 55.8 kJ/mol, enhancing carbodiimide production understanding.

Keywords:
DFTactivation energycarbodiimidegas volumetryisocyanateorganocatalysisreaction kinetics

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Area of Science:

  • Organic Chemistry
  • Chemical Kinetics
  • Computational Chemistry

Background:

  • Carbodiimides are vital crosslinkers in organic synthesis and additives in the isocyanate industry.
  • Understanding carbodiimide formation mechanisms is crucial for optimizing their production and applications.

Purpose of the Study:

  • To investigate the formation of diphenylcarbodiimide (CDI) from phenyl isocyanate.
  • To elucidate the reaction mechanism using a phosphorus-based catalyst (MPPO) in ortho-dichlorobenzene (ODCB).
  • To compare theoretical calculations with experimental kinetic data.

Main Methods:

  • Theoretical investigation using Density Functional Theory (DFT) with B3LYP/6-31G(d) and SMD solvent model.
  • Experimental kinetic study based on volumetric quantification of evolved CO2 at temperatures ranging from 40 to 80 °C.
  • Analysis of reaction kinetics using Arrhenius plots to determine experimental activation energy.

Main Results:

  • A detailed two-part reaction mechanism for diphenylcarbodiimide formation was proposed, supported by DFT calculations.
  • The rate-determining step in the first part of the mechanism has an enthalpy barrier of 52.9 kJ/mol.
  • Experimental activation energy (55.8 ± 2.1 kJ/mol) closely matched the computational results, validating the proposed mechanism.

Conclusions:

  • The study provides a comprehensive understanding of diphenylcarbodiimide production from phenyl isocyanate.
  • Excellent agreement between theoretical and experimental data validates the detailed reaction mechanism.
  • Findings contribute to the optimization of carbodiimide synthesis and its industrial applications.