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Relative Reactivity of Carboxylic Acid Derivatives

Relative Reactivity of Carboxylic Acid Derivatives

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

Substituent Effects on Acidity of Carboxylic Acids

Substituent Effects on Acidity of Carboxylic Acids

The acidity of carboxylic acids is influenced by the nature of the substituents bounded to the functional group. The acid strength is determined by the stability of the carboxylate anion—the conjugate base formed by dissociating the corresponding carboxylic acid.

Reactions of Carboxylic Acids: Introduction

Reactions of Carboxylic Acids: Introduction

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.

Nucleophilic Substitution Reactions

Nucleophilic Substitution Reactions

Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...

SN1 Reaction: Kinetics

S_N1 Reaction: Kinetics

In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to the SN2 mechanism despite using a strong nucleophile.
However, Sir Christopher Ingold and Edward D. Hughes, who studied the kinetics of various nucleophilic substitution reactions, noticed that a tertiary alkyl halide does undergo a nucleophilic substitution reaction in the presence of a weak nucleophile. While studying the substitution...

Electrophilic Aromatic Substitution: Overview

Electrophilic Aromatic Substitution: Overview

In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.

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Related Experiment Video

Updated: Dec 26, 2025

Determination of the Gas-phase Acidities of Oligopeptides

Determination of the Gas-phase Acidities of Oligopeptides

Published on: June 24, 2013

Reactivity Parameters and Substitution Effect in Organic Acids.

Jishnudas Chakkamalayath¹, K R S Chandrakumar², Swapan K Ghosh³

¹Indian Institute of Science Education and Research (IISER), Thiruvananthapuram, 695551, India.

The Journal of Physical Chemistry. A

|March 14, 2020

Summary

This study compares density functional theory reactivity indices to assess chemical reactivity. Fugality and atom-atom polarizability effectively predict the acidic strength of substituted benzoic acids.

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Area of Science:

Theoretical Chemistry
Quantum Chemistry
Computational Chemistry

Background:

Density functional theory (DFT) provides valuable insights into chemical reactivity.
Reactivity indices derived from DFT are crucial for understanding chemical phenomena.
Existing indices may require further refinement for specific applications.

Purpose of the Study:

To intercompare various DFT-based reactivity indices.
To evaluate the application of fugality and atom-atom polarizability.
To investigate the acidic strength of para-substituted benzoic acid derivatives.

Main Methods:

Utilizing density functional theory (DFT) calculations.
Applying concepts of fugality and atom-atom polarizability.
Correlating reactivity parameters with experimental pKa values.

Main Results:

Demonstrated the utility of fugality and atom-atom polarizability for predicting acidity.
Established correlations between reactivity indices and pKa values.
Identified trends in reactivity parameters for substituted benzoic acids.

Conclusions:

DFT-based reactivity indices, specifically fugality and atom-atom polarizability, are effective tools for studying chemical reactivity.
These indices offer valuable insights into the acidic strength of benzoic acid derivatives.
The study highlights the applicability of these concepts to chemical problems.