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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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...
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.
Precipitation of Ions03:11

Precipitation of Ions

Predicting Precipitation
The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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).
Precipitation Processes01:12

Precipitation Processes

The experimental conditions in a gravimetric analysis should be optimized to maximize the particle size and purity of the obtained precipitate. Ideally, the concentration of the precipitating reagent should be low with effective stirring to maintain low relative supersaturation for the growth of large crystals. In homogeneous precipitation, the precipitant is slowly generated by a chemical reaction in the solution to avoid local reagent excesses. For example, urea decomposes gradually to...
Precipitation and Co-precipitation01:17

Precipitation and Co-precipitation

Precipitation and coprecipitation methods can be used to separate a mixture of ions in a solution. In qualitative inorganic analysis, ions that form sparingly soluble precipitates with the same reagent are separated based on the differences in solubility products. For example, consider the separation of Cu(II) and Fe(II) ions by precipitation as insoluble sulfides. First, copper(II) sulfide is precipitated by the addition of acidic H2S, where the dissociation of H2S is suppressed. Adding H2S...

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Updated: May 21, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Precipitation-driven self-sorting of imines.

Rio Carlo Lirag1, Karolina Osowska, Ognjen Š Miljanić

  • 1University of Houston, Department of Chemistry, 136 Fleming Building, Houston, TX 77204-5003, USA.

Organic & Biomolecular Chemistry
|May 31, 2012
PubMed
Summary
This summary is machine-generated.

Carefully controlled precipitation conditions enable the selective formation of specific imine products from aromatic aldehydes and anilines. Differences in imine solubility within ethanol-water mixtures drive this self-sorting process.

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Imine formation is a fundamental reaction in organic synthesis.
  • Controlling the selectivity of reactions involving multiple potential products remains a challenge.
  • Solubility plays a critical role in precipitation-based separation techniques.

Purpose of the Study:

  • To investigate the self-sorting of imine products from aromatic aldehydes and anilines.
  • To demonstrate the influence of precipitation conditions on reaction selectivity.
  • To explore the role of solubility in achieving selective product formation.

Main Methods:

  • Utilizing precipitation reactions with mixtures of aromatic aldehydes and substituted anilines.
  • Employing ethanol-water solvent mixtures to control solubility.
  • Analyzing the resulting imine products to determine selectivity.

Main Results:

  • Achieved self-sorting of equilibrating mixtures into a limited number of imine products.
  • Demonstrated high selectivity in imine formation through judicious choice of precipitation conditions.
  • Correlated the observed selectivity with the differential solubility of various imine products in the EtOH-H(2)O solvent system.

Conclusions:

  • Precipitation conditions can be strategically employed to control the self-sorting and selective formation of imine products.
  • Solubility differences are the key driving force for achieving high selectivity in this system.
  • This approach offers a novel method for the targeted synthesis and separation of imine compounds.