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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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...
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).
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Published on: February 7, 2017

Electrochemically controlled multiple hydrogen bonding between triarylamines and imidazoles.

Hsu-Chun Cheng1, Kuo Yuan Chiu, Yi-Jung Tu

  • 1Department of Applied Chemistry, National Chi Nan University, 1 University Road, Puli 545, Nantou, Taiwan.

Organic Letters
|July 26, 2013
PubMed
Summary

Researchers electrochemically controlled hydrogen bonding in triarylamine derivatives by adjusting amino substituents. This electrochemical control influences interactions between oxidized triarylamine and imidazole, confirmed by DFT calculations.

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Published on: August 22, 2018

Area of Science:

  • Electrochemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Triarylamines are versatile organic compounds with applications in materials science.
  • Hydrogen bonding plays a crucial role in molecular interactions and material properties.
  • Controlling intermolecular interactions electrochemically offers novel pathways for material design.

Purpose of the Study:

  • To investigate the electrochemical control of hydrogen bonding between oxidized triarylamines and imidazole.
  • To understand how the number of amino substituents affects these interactions.
  • To correlate electrochemical behavior with computational predictions.

Main Methods:

  • Cyclic voltammetry (CV) was employed to study the electrochemical behavior.
  • Varying numbers of amino substituents were introduced onto the triarylamine core.
  • Density Functional Theory (DFT) calculations were performed to analyze electronic properties.

Main Results:

  • Electrochemical control over hydrogen bonding extent was achieved by modifying amino substituents.
  • Three distinct electrochemical behaviors were observed, correlating with triarylamine-imidazole interactions.
  • DFT calculations confirmed reduced proton electron density with increased amino groups.

Conclusions:

  • The number of amino substituents on triarylamine is a key factor in electrochemically controlling hydrogen bonding.
  • Electrochemical methods can effectively modulate the interaction strength between oxidized triarylamines and imidazole.
  • Computational insights support the experimental findings regarding electronic structure modifications.