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Related Concept Videos

Micelles01:30

Micelles

260
Micelle formation is an intricate process that hinges on the properties of amphiphilic or amphipathic molecules and the conditions of the system in which they are found. Amphiphilic molecules, which have both hydrophilic (water-attracting) and hydrophobic (water-repelling) parts, play a critical role in this process.In aqueous environments, these molecules arrange themselves such that their hydrophilic heads are turned towards the water phase, while their hydrophobic tails are oriented away...
260
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

5.1K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
5.1K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

10.9K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
10.9K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.7K
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...
4.7K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

10.1K
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...
10.1K
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

9.1K
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...
9.1K

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Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
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Micelle Formation in Liquid Ammonia.

Joseph M Griffin1, John H Atherton1, Michael I Page1

  • 1IPOS, The Page Laboratories, Department of Chemical and Biological Sciences, The University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, United Kingdom.

The Journal of Organic Chemistry
|June 16, 2015
PubMed
Summary

Perfluorinated amides and carboxylates form micelles in liquid ammonia and water, with properties influenced by chain length and solvent. These micelles can catalyze reactions and exhibit unique hydrophobic behaviors, potentially relevant to extraterrestrial life.

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Area of Science:

  • Supramolecular Chemistry
  • Fluorinated Compounds
  • Physical Chemistry

Background:

  • Perfluorinated long chain alkyl amides exhibit concentration-dependent aggregation in liquid ammonia, indicative of micelle formation.
  • Changes in (19)F NMR chemical shifts confirm micelle-type structures.
  • Perfluorinated carboxylates also form ion pairs in liquid ammonia, with strong interchain interactions.

Purpose of the Study:

  • To investigate micelle formation and catalytic activity of perfluorinated amides in liquid ammonia.
  • To analyze the aggregation behavior and hydrophobic interactions of perfluorinated carboxylates in both liquid ammonia and aqueous solutions.
  • To compare the hydrophobic characteristics of fluorinated and non-fluorinated compounds in different solvents.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy, specifically (19)F NMR, to study aggregation.
  • Determination of critical micelle concentrations (cmc) in liquid ammonia and water.
  • Calculation of Kleven parameters (A and B) to characterize micelle formation.
  • Analysis of equilibrium dissociation constants for ion pairs.

Main Results:

  • Critical micelle concentrations (cmc) for perfluorinated amides decrease with increasing chain length in liquid ammonia (Kleven parameters A=0.18, B=0.19).
  • Perfluorinated amide micelles catalyze ester ammonolysis in liquid ammonia.
  • Perfluorinated carboxylates show favorable interchain interactions in liquid ammonia, forming micelles in aqueous solution with a higher Kleven B-value (0.52) than analogous alkyl carboxylates (0.30).

Conclusions:

  • Perfluorinated amides and carboxylates display distinct aggregation behaviors in liquid ammonia and water, driven by both electrostatic and hydrophobic forces.
  • The catalytic activity of perfluorinated micelles in ammonolysis reactions is demonstrated.
  • Differences in CH2 and CF2 unit hydrophobicity are highlighted, with implications for potential ammonia-based life forms.