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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

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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).
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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each...
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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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3-Methylpiperidinium ionic liquids.

Tayeb Belhocine1, Stewart A Forsyth, H Q Nimal Gunaratne

  • 1The QUILL Research Centre, School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Stranmillis Road, Belfast BT9 5AG, UK.

Physical Chemistry Chemical Physics : PCCP
|February 12, 2015
PubMed
Summary
This summary is machine-generated.

New room temperature ionic liquids based on the 3-methylpiperdinium cation were synthesized. These ionic liquids exhibit excellent electrochemical stability, expanding options for high-performance electrolytes.

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Area of Science:

  • Materials Science
  • Electrochemistry
  • Organic Chemistry

Background:

  • Ionic liquids (ILs) are salts with low melting points, offering unique solvent properties.
  • Piperidinium-based ILs are explored for electrochemical applications due to their stability.
  • Tailoring cation structure influences IL properties like viscosity and conductivity.

Purpose of the Study:

  • To synthesize and characterize novel room temperature ionic liquids (RTILs) using the 3-methylpiperdinium cation.
  • To investigate the effect of cation structure and anion type on the physical properties of these ILs.
  • To evaluate the electrochemical stability of the synthesized 3-methylpiperdinium ILs.

Main Methods:

  • Synthesis of tertiary amines via alkylation of 3-methylpiperidine, followed by quaternization.
  • Anion metathesis to introduce the bis(trifluoromethylsulfonyl)imide ([NTf2](-)) anion.
  • Characterization of physical properties (density, viscosity, ionic conductivity) and crystal structure determination.
  • Cyclic voltammetry to assess electrochemical stability.

Main Results:

  • A series of 3-methylpiperdinium-based ILs were successfully synthesized, with [NTf2](-) salts showing room temperature liquid behavior.
  • Alkyl-substituted [Rmmβpip]X salts were low-melting solids, while ether-functionalized analogues were RTILs.
  • No crystallization was observed for these ILs even below 0 °C.
  • Systematic analysis revealed trends in density, viscosity, and ionic conductivity based on cation structure.
  • All synthesized 3-methylpiperdinium ILs demonstrated exceptional electrochemical stability.

Conclusions:

  • The 3-methylpiperdinium cation provides a versatile platform for designing room temperature ionic liquids.
  • Ether functionalities on the cation significantly enhance liquidity at room temperature.
  • These novel ILs offer a promising alternative for safe and high-performance electrolytes in various electrochemical applications.
  • The study provides valuable structure-property relationships for piperidinium-based ionic liquids.