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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

10.2K
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...
10.2K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.2K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.2K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

7.8K
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.
7.8K
Structure of Amines01:19

Structure of Amines

3.5K
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’...
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Adsorption-driven self-sorting of dynamic imine libraries.

Chia-Wei Hsu1, Ognjen Š Miljanić

  • 1Department of Chemistry, University of Houston, 112 Fleming Building, Houston, TX 77204-5003 (USA).

Angewandte Chemie (International Ed. in English)
|December 23, 2014
PubMed
Summary
This summary is machine-generated.

Dynamic imine mixtures simplify during column chromatography. Components continuously exchange constituents, favoring extreme polarity molecules and reducing complexity from 16 to 4 major products.

Keywords:
chemoselectivitycolumn chromatographydynamic combinatorial chemistryself-sortingsystems chemistry

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Area of Science:

  • Chemical separations
  • Supramolecular chemistry
  • Origins of life studies

Background:

  • Adsorption differences in complex mixtures are crucial for separations, sensing, and catalysis.
  • Dynamic equilibrium in chemical mixtures can influence their behavior and composition.
  • Imine chemistry is relevant to understanding complex molecular systems.

Purpose of the Study:

  • To investigate the compositional changes of dynamic imine mixtures during column chromatography.
  • To demonstrate how dynamic equilibrium can lead to mixture simplification.
  • To explore the implications for chemical separations and origins of life theories.

Main Methods:

  • Utilized column chromatography to separate imine mixtures.
  • Analyzed the dynamic exchange of aldehyde and amine constituents within imines.
  • Monitored the evolution of imine library composition over the chromatographic process.

Main Results:

  • Dynamic imine mixtures showed significant simplification during chromatography.
  • Continuous exchange of imine constituents favored molecules with extreme polarities.
  • Imine libraries with up to 16 members were reduced to 4 major products.

Conclusions:

  • Dynamic equilibrium in imine mixtures drives compositional simplification in chromatography.
  • This process preferentially forms molecules at polarity extremes, reducing intermediate species.
  • The findings have implications for designing efficient separation techniques and understanding prebiotic chemistry.