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Related Concept Videos

Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

5.7K
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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Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.3K
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...
3.3K
Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

5.7K
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...
5.7K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

2.7K
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...
2.7K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.5K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.5K
Ion Exchange01:17

Ion Exchange

560
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...
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Tris(2-hydroxyethyl)ammonium-Based Protic "Ionic Liquids": Synthesis and Characterization.

Emilia Tojo1, Alexandra Cáceres2, Alba Somoza2

  • 1Department of Organic Chemistry, Faculty of Chemistry, Universidade de Vigo, 36210 Vigo, Spain.

Journal of Chemical and Engineering Data
|October 17, 2024
PubMed
Summary
This summary is machine-generated.

Protic ionic liquids (PILs) synthesis often results in incomplete proton transfer, leading to mixtures of parent compounds and ions. This study highlights the low ionicity of certain PILs, cautioning against their use as pure ionic compounds.

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Area of Science:

  • Materials Science
  • Chemical Synthesis
  • Physical Chemistry

Background:

  • Protic ionic liquids (PILs) synthesis is frequently incomplete, resulting in coexisting parent compounds and ionic species.
  • The term "ionic liquid" is often applied to PILs without rigorous ionicity assessment, potentially impacting their application.
  • Tris(2-hydroxyethyl)ammonium-based PILs with specific anions are of interest due to low toxicity and biopolymer interaction capabilities.

Purpose of the Study:

  • To investigate the ionicity and thermal properties of tris(2-hydroxyethyl)ammonium-based protic ionic liquids.
  • To propose improved synthesis methods for PILs, focusing on solvent-free conditions and moderate temperatures.
  • To evaluate the suitability of the term "ionic liquid" for these synthesized systems.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy was employed to determine the ionicity of the synthesized PILs.
  • Thermal characterization, including isothermal thermogravimetric analysis, was performed.
  • Solvent-free synthesis at moderate temperatures was explored to minimize reactant decomposition.

Main Results:

  • The ionicity of the studied tris(2-hydroxyethyl)ammonium-based PILs ranged from 20% to 86%, indicating significant coexisting un-ionized species.
  • Mass loss for these PILs commenced around 350 K, with minimal influence of the anion on thermal stability.
  • The proposed solvent-free synthesis method aimed to reduce impurities from reactant decomposition.

Conclusions:

  • The term "ionic liquid" should be used with caution for systems with partial ionicity, as un-ionized species coexist with ionic forms.
  • The findings necessitate consideration of both ionic and neutral species in applications involving these PILs.
  • The synthesis approach offers potential improvements for producing PILs with reduced impurities.