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Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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Amines to Amides: Acylation of Amines01:19

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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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...
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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

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Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
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Acidity and Basicity of Carboxylic Acid Derivatives01:25

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Carboxylic acids are the strongest among organic acids, as they readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion. In comparison, the acid derivatives lack acidic hydrogens directly attached to a functional group. In these compounds, the acidic nature arises from their ability to lose α hydrogens, making them weakly acidic.
The relative acidic strength of the derivatives can be explained based on the extent of resonance stabilization of the conjugate base. The...
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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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What Makes Oxidized N-Acylanthranilamides Stable?

Eli M Espinoza1, Jillian M Larsen2, Valentine I Vullev1,2,3,4

  • 1Department of Chemistry, University of California , Riverside, California 92521, United States.

The Journal of Physical Chemistry Letters
|February 11, 2016
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Summary
This summary is machine-generated.

Anthranilamide (Aa) derivatives enable directional charge transfer via hole hopping. Stabilizing these molecules requires specific electrochemical potentials and substituent placement to prevent oxidative degradation, crucial for designing efficient hole-transfer materials.

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Area of Science:

  • Organic chemistry
  • Materials science
  • Electrochemistry

Background:

  • Oligoamides derived from anthranilic acid show potential for directed, long-range charge transfer.
  • Hole hopping, influenced by anthranilamide (Aa) dipoles, is a key mechanism for charge transduction.
  • Oxidative decomposition of amides limits their use in hole-hopping pathways.

Purpose of the Study:

  • To investigate methods for preventing oxidative degradation of N-acylated Aa derivatives.
  • To stabilize radical cations of aromatic amides for improved charge transfer applications.
  • To establish design principles for robust hole-transfer amides.

Main Methods:

  • Electrochemical analysis to determine oxidation potentials.
  • Computational analysis to understand radical cation stability.
  • Synthesis and characterization of N-acylated anthranilamide derivatives.

Main Results:

  • Identified two key requirements for stabilizing radical cations: oxidation potential < 1.4 V vs SCE and para-substituted electron-donating groups.
  • Demonstrated that specific structural modifications prevent radical cation spin density overlap with the amide linkage.
  • Confirmed the feasibility of suppressing oxidative degradation in aromatic amides.

Conclusions:

  • Achieving stable radical cations in aromatic amides is possible through controlled oxidation potentials and strategic substituent placement.
  • These findings are critical for designing stable and efficient hole-transfer amides for electronic applications.
  • The study provides a foundational understanding for developing new materials for charge transport mediation.