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Related Concept Videos

Relative Reactivity of Carboxylic Acid Derivatives01:13

Relative Reactivity of Carboxylic Acid Derivatives

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Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of reactivity.
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
Halide ions < Acyloxy ions < Alkoxy ions < Amine ions
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Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

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Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
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Leveling Effect and Non-Aqueous Acid-Base Solutions02:11

Leveling Effect and Non-Aqueous Acid-Base Solutions

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This lesson defines the leveling effect in acidic and basic solutions and its role in aqueous and non-aqueous solutions. It is essential to understand the competing nature of various species in a chemical system.
The Leveling Effect of a Solvent
A generic acid (HA) reacts with the generic base (B-) to yield the corresponding conjugate base (A-) and conjugate acid (HB):
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F&#8722;
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Revisiting photoacidity using R*NH2 photoacids.

H Rozler1, D Aminov1, D Pines1

  • 1Department of Chemistry, Ben Gurion University of the Negev, Beer-Sheva 84105, Israel.

The Journal of Chemical Physics
|April 2, 2026
PubMed
Summary
This summary is machine-generated.

This study compares proton transfer reactions in R*NH2 and R*OH photoacids. Similar mechanisms were found, with differences attributed to solvent reorganization energy, impacting proton dissociation rates.

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Area of Science:

  • Photochemistry
  • Chemical Kinetics
  • Physical Chemistry

Background:

  • Neutral photoacids, R*NH2 and R*OH, are crucial in understanding proton transfer dynamics.
  • Proton transfer reactions are fundamental in various chemical and biological processes.
  • Excited-state lifetimes significantly influence the observable proton transfer pathways.

Purpose of the Study:

  • To compare time-resolved and steady-state proton transfer reactions in R*NH2 and R*OH photoacids.
  • To analyze these reactions using free-energy correlations.
  • To elucidate the role of solvent reorganization energy in observed differences.

Main Methods:

  • Utilized time-resolved and steady-state fluorescence spectroscopies.
  • Constructed free-energy correlations for R*NH2 photoacids with strong Brønsted bases.
  • Compared these correlations with existing data for R*OH photoacids.

Main Results:

  • Identified significant similarities in proton transfer mechanisms between R*NH2 and R*OH photoacids.
  • Attributed differences in free-energy correlations to variations in local solvent reorganization energy.
  • Demonstrated that R*NH2 photoacids are generally too weak to dissociate protons within their excited-state lifetime.

Conclusions:

  • Proton transfer mechanisms in R*NH2 and R*OH photoacids share common features.
  • Solvent effects, specifically reorganization energy, play a key role in modulating proton transfer.
  • Free-energy correlations provide valuable insights into the kinetics and thermodynamics of photoacid proton transfer.