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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: 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...
Preparation of Amides01:29

Preparation of Amides

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...
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).
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...
EDTA: Chemistry and Properties01:22

EDTA: Chemistry and Properties

Polydentate ligands are most widely used in complexometric titrations because they form more stable complexes with the metal ions than mono- or bidentate ligands due to the chelate effect. Examples of polydentate ligands are ethylenediaminetetraacetic acid (EDTA), crown ethers, and cryptands. The most important feature of optimal polydentate ligands is the ability to form 1:1 complexes in a single-step process. Amino carboxylic acid derivatives are frequently used as complexing agents. EDTA is...

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Carbamate complexation by urea-based receptors: studies in solution and the solid state.

Peter R Edwards1, Jennifer R Hiscock, Philip A Gale

  • 1School of Chemistry, University of Southampton, Southampton, UK.

Organic & Biomolecular Chemistry
|December 22, 2009
PubMed
Summary

Urea-based receptors effectively bind carbon dioxide (CO2) anions through hydrogen bonding, stabilizing CO2 adducts. This work demonstrates competition with electrostatic forces in CO2 capture systems.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Chemical Crystallography

Background:

  • Urea derivatives are versatile scaffolds in supramolecular chemistry.
  • Carbon dioxide (CO2) capture remains a critical challenge in environmental science.
  • Hydrogen bonding plays a crucial role in molecular recognition and stabilization.

Purpose of the Study:

  • To investigate the hydrogen bonding interactions between urea-based receptors and CO2-derived anions.
  • To explore the stabilization of CO2 adducts through host-anion interactions.
  • To understand the competition between hydrogen bonding and electrostatic interactions in anion binding.

Main Methods:

  • Synthesis and characterization of urea-based neutral hydrogen bond donor anion receptors.
  • Spectroscopic analysis (NMR) to study host-anion interactions.
  • Synchrotron X-ray crystallography to elucidate complex structures.

Main Results:

  • Significant downfield shifts of urea NH protons indicate strong hydrogen bonding interactions.
  • Urea receptors successfully stabilize alkylcarbamate anions, outcompeting electrostatic interactions.
  • A ternary complex structure reveals extensive hydrogen bonding (six bonds) to the carbamate group.

Conclusions:

  • Urea-based receptors are effective in recognizing and stabilizing CO2-derived anions via hydrogen bonding.
  • This study provides insights into designing efficient CO2 capture agents.
  • Structural data confirms the critical role of hydrogen bonding in stabilizing CO2 adducts.