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Related Concept Videos

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).
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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This lesson defines the leveling effect in acidic and basic solutions and its role in aqueous and non-aqueous solutions. It is essential to understand the competing nature of various species in a chemical system.
The Leveling Effect of a Solvent
A generic acid (HA) reacts with the generic base (B-) to yield the corresponding conjugate base (A-) and conjugate acid (HB):
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...
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Ligand-gated ion channels are transmembrane proteins that play a vital role in intercellular communication and functions of the nervous system. They allow the influx of ions across the membrane once the neurotransmitter binds, allowing the subsequent transmission of electrical excitation across the neurons. Other ligand-gated ion channels, like the γ-aminobutyric acid (GABA) receptor, permit anions like chloride into the cells on the binding of the GABA molecule. Their entry into the cell...

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Fluorous effects in amide-based receptors for anions.

Jesse V Gavette1, Jacqueline M McGrath, Anne M Spuches

  • 1Department of Chemistry, Science and Technology Building, East Carolina University, Greenville, North Carolina 27858-4353, USA.

The Journal of Organic Chemistry
|April 11, 2009
PubMed
Summary

New hybrid receptors selectively bind perfluorooctanesulfonate (PFOS) and related anions. These fluorous receptors show strong binding affinities, unlike hydrocarbon analogs, enabling potential applications in anion recognition and sensing.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Analytical Chemistry

Background:

  • Perfluorooctanesulfonate (PFOS) is a persistent environmental pollutant.
  • Selective recognition of specific anions remains a challenge in chemistry.
  • Designing receptors for both headgroup and tail interactions is complex.

Purpose of the Study:

  • To develop novel hybrid receptors capable of recognizing both the sulfonate headgroup and the fluorous tail of PFOS.
  • To investigate the binding affinities and selectivity of these receptors towards various anions.
  • To understand the structural and electronic factors governing the host-guest interactions.

Main Methods:

  • Synthesis of hybrid receptors by coupling fluorinated carboxylic acids onto poly(aminomethyl)benzene scaffolds.
  • Characterization of anion binding using proton nuclear magnetic resonance ((1)H NMR) spectroscopy.
  • Quantitative analysis of binding constants via isothermal titration calorimetry (ITC).

Main Results:

  • Hybrid receptors demonstrated strong binding to PFOS and other anions in chloroform, with association constants (K(assoc)) greater than 1000 M(-1).
  • Significant downfield shifts in amide NH protons and heat evolution confirmed hydrogen-bonding interactions.
  • Analogous hydrocarbon receptors exhibited weak binding (K(assoc) < 50 M(-1)), highlighting the importance of fluorous interactions.

Conclusions:

  • The designed fluorous receptors exhibit high affinity and selectivity for PFOS and related anions.
  • The enhanced binding is attributed to the synergistic recognition of both the sulfonate headgroup and the fluorous tail.
  • Ab initio calculations suggest that differences in NH donor acidity do not explain the observed binding strength variations.