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Related Concept Videos

Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates higher...
Ions as Acids and Bases02:54

Ions as Acids and Bases

Salts with Acidic Ions
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:
Ion Exchange01:17

Ion Exchange

Ion exchange chromatography separates charged molecules from a solution by reversibly exchanging them with mobile, or 'active', ions associated with the oppositely charged stationary phase. This method can be used to separate ions, soften and deionize water, and purify solutions. The polymers comprising the ion-exchange column are high-molecular-weight and chemically stable polymers, crosslinked to be porous and essentially insoluble. They are also functionalized with either acidic or basic...
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).
Alkyl Halides02:45

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

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Related Experiment Video

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Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature
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Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature

Published on: December 20, 2016

Protic ionic liquids based on phosphonium cations: comparison with ammonium analogues.

Usman Ali Rana1, R Vijayaraghavan, Mareike Walther

  • 1Materials Engineering Department, Monash University, Clayton VIC, 3800, Australia. usmanali.rana@monash.edu

Chemical Communications (Cambridge, England)
|October 4, 2011
PubMed
Summary

New protic ionic liquids (PILs) using phosphonium cations offer superior thermal stability and conductivity over ammonium versions. These phosphonium-based ILs also demonstrate easier proton reduction, enhancing their potential applications.

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

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Last Updated: May 28, 2026

Synthesis of Ionic Liquid Based Electrolytes, Assembly of Li-ion Batteries, and Measurements of Performance at High Temperature
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
12:06

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

Area of Science:

  • Electrochemistry
  • Materials Science
  • Ionic Liquids

Background:

  • Protic ionic liquids (PILs) are salts that are liquid at ambient temperatures and contain a transferable proton.
  • Ionic liquids (ILs) are salts that are liquid below 100 °C and are composed of ions.
  • Developing novel ILs with enhanced properties is crucial for various electrochemical applications.

Purpose of the Study:

  • To synthesize and characterize novel protic ionic liquids (PILs) based on a tributyl phosphonium cation.
  • To compare the properties of phosphonium-based PILs with their ammonium-based counterparts.
  • To evaluate the potential of these novel PILs in applications requiring high ionic conductivity and proton reduction.

Main Methods:

  • Synthesis of phosphonium-based protic ionic liquids.
  • Characterization using techniques such as NMR spectroscopy, thermal analysis (TGA/DSC), and electrochemical impedance spectroscopy.
  • Proton reduction studies.

Main Results:

  • Successful synthesis and characterization of novel phosphonium-based PILs.
  • Phosphonium-based PILs exhibited higher thermal stability compared to ammonium-based PILs.
  • Enhanced ionic conductivity was observed in phosphonium-based PILs.
  • Facile proton reduction was demonstrated for the phosphonium-based ILs.

Conclusions:

  • Tributyl phosphonium-based protic ionic liquids represent a promising class of materials.
  • These novel PILs offer significant advantages in thermal stability, ionic conductivity, and proton reduction capabilities over ammonium-based analogues.
  • The findings suggest potential applications in areas such as batteries, fuel cells, and electrocatalysis.