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Related Concept Videos

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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.
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

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...
Types of Enols and Enolates01:19

Types of Enols and Enolates

Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional instability of enols...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

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Crystal structures of proline-derived enamines.

Dominique Anna Bock1, Christian W Lehmann, Benjamin List

  • 1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Muelheim an der Ruhr, Germany.

Proceedings of the National Academy of Sciences of the United States of America
|November 12, 2010
PubMed
Summary

Researchers isolated and characterized proline enaminones derived from aldehydes and ketones. Crystal structures revealed stereochemical details, including double bond configuration and carboxylate positioning, compared with computational models.

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Computational Chemistry

Background:

  • Proline enaminones are versatile synthetic intermediates.
  • Understanding their stereochemical properties is crucial for asymmetric synthesis.

Purpose of the Study:

  • To isolate and structurally characterize aldehyde- and ketone-derived proline enaminones.
  • To investigate the stereochemical aspects of proline enamine crystal structures.
  • To compare experimental crystal structures with density functional theory (DFT) calculations.

Main Methods:

  • Isolation and purification of proline enaminones.
  • Single-crystal X-ray diffraction for structural determination.
  • Density functional theory (DFT) calculations for ground and transition states.

Main Results:

  • Successful isolation and characterization of various proline enaminones.
  • Detailed analysis of double bond configuration and carboxylate positioning in 10 proline enamine crystal structures.
  • Comparison of experimental structures with DFT-calculated structures, including transition states.

Conclusions:

  • The study provides comprehensive structural and stereochemical insights into proline enaminones.
  • Experimental data validates computational models for ground and transition states.
  • Findings contribute to a deeper understanding of enamine chemistry and reaction mechanisms.