Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

20.9K
The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
20.9K
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

4.2K
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
4.2K
Esters to Carboxylic Acids: Saponification01:25

Esters to Carboxylic Acids: Saponification

6.7K
Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
6.7K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

10.2K
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
10.2K
Solvating Effects02:12

Solvating Effects

9.1K
An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
9.1K
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

3.6K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
3.6K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Combining PC-SAFT and ML to Access Unknown API Solubilities.

Molecular pharmaceutics·2026
Same author

The More the Better?─Vitamin E TPGS as a Release Enhancer for Ritonavir/PVPVA Amorphous Solid Dispersions.

Molecular pharmaceutics·2025
Same author

The Hidden Crux of Correctly Determining Octanol-Water Partition Coefficients.

Molecular pharmaceutics·2025
Same author

Water-Assisted Drying of PVPVA-Based Amorphous Solid Dispersions.

Molecular pharmaceutics·2025
Same author

Water Activity as an Indicator for Antibody Storage Stability in Lyophilized Formulations.

Molecular pharmaceutics·2025
Same author

Simultaneous Water Sorption and Crystallization in ASDs 2: Modeling Long-Term Stabilities.

Molecular pharmaceutics·2024
Same journal

Spectroscopic Investigation of the In Vivo Light-Dependent Photodynamics of the Marine Diatom Phaeodactylum tricornutum.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same journal

Atomistic Insights into the Thermal Decomposition and Runaway Mechanism of Peroxypropionic Acid.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same journal

Hydrazine Adsorption on Hexagonal Ice (0001): First-Principles Investigations on Stability, Dynamics, and Chirality Changes.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same journal

Sustainable Ball Milling-Assisted Synthesis of Bread Waste-Derived Highly Porous Carbons for Adsorption-Based Applications.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same journal

RNALig: An ML-Driven Structure-Based Scoring Function for Estimating Binding Affinities of RNA-Ligand Complexes.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same journal

Photoswitchable Polar Azobenzene-Based Liquid Crystals for Electro-Optic and Optical Data Storage Applications.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
See all related articles

Related Experiment Video

Updated: Mar 1, 2026

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes
09:42

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes

Published on: January 16, 2016

9.4K

Predicting the Solvent Effect on Esterification Kinetics.

Max Lemberg1, Gabriele Sadowski1

  • 1Laboratory for Thermodynamics, Department Biochemical & Chemical Engineering, TU Dortmund University, Emil-Figge-Str. 70, 44227, Dortmund, Germany.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|May 31, 2017
PubMed
Summary
This summary is machine-generated.

Solvents significantly impact reaction rates, but classical models fail. This study used the PC-SAFT model to accurately predict solvent effects on esterification kinetics, identifying solvent-independent constants.

Keywords:
activity coefficientsesterificationreaction kineticssolvent effectsthermodynamic model

More Related Videos

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

37.8K
Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
09:08

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

Published on: April 2, 2018

36.2K

Related Experiment Videos

Last Updated: Mar 1, 2026

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes
09:42

Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes

Published on: January 16, 2016

9.4K
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

37.8K
Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
09:08

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

Published on: April 2, 2018

36.2K

Area of Science:

  • Chemical Engineering
  • Physical Chemistry
  • Reaction Kinetics

Background:

  • Solvents are known to influence chemical reaction kinetics.
  • Classical concentration-based kinetic modeling cannot adequately describe these solvent effects.
  • Understanding solvent influence is crucial for optimizing chemical processes.

Purpose of the Study:

  • To investigate the effect of different solvents on the reaction kinetics of esterification.
  • To develop a model that accounts for solvent-solute interactions.
  • To identify solvent-independent kinetic parameters.

Main Methods:

  • Studied esterification reactions of acetic acid and propionic acid with ethanol at 303.15 K.
  • Applied the PC-SAFT (Perturbed-Chain Statistical Associating Fluid Theory) thermodynamic model.
  • Utilized activity coefficients to quantify solute-solvent interactions.

Main Results:

  • Reactant ratio and solvents (acetonitrile, tetrahydrofuran, dimethylformamide) significantly affected reaction rates.
  • The PC-SAFT model successfully predicted solvent effects on kinetics.
  • Obtained almost quantitative agreement between predicted and experimental data.
  • Identified solvent-independent kinetic constants.

Conclusions:

  • Thermodynamic non-idealities must be considered for accurate kinetic modeling in different solvents.
  • The PC-SAFT approach provides a reliable method for predicting solvent effects.
  • This method reduces the experimental effort required to select optimal solvents for reactions.