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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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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.
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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.
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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.
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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.
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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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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.
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CC-stretched formic acid: isomerisation, dimerisation, and carboxylic acid complexation.

Katharina A E Meyer1, Arman Nejad

  • 1Institute of Physical Chemistry, University of Göttingen, Tammannstr. 6, 37077 Göttingen, Germany. katharina.meyer@chemie.uni-goettingen.de anejad@gwdg.de.

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Summary

This study reveals the vibrational spectra of propiolic acid rotamers using Raman jet spectroscopy. It identifies new spectral features and provides benchmarks for computational chemistry methods.

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Area of Science:

  • Physical Chemistry
  • Spectroscopy
  • Computational Chemistry

Background:

  • Understanding molecular conformations and their vibrational properties is crucial for chemical analysis.
  • Propiolic acid (HC≡C-COOH) is a simple alkyne carboxylic acid whose cis-trans isomerism and vibrational spectra are not fully characterized.

Purpose of the Study:

  • To investigate the cis-trans isomerism of propiolic acid using high-resolution spectroscopy.
  • To obtain environment-free vibrational data for both cis and trans conformers.
  • To benchmark computational methods for predicting vibrational spectra.

Main Methods:

  • Linear Raman jet spectroscopy was employed to record vibration-rotation spectra.
  • High-level electronic structure calculations, including vibrational perturbation theory (VPT2), were performed.
  • Comparison with literature data for other carboxylic acid dimers was conducted.

Main Results:

  • The first environment-free vibrational band centers for the higher-energy cis-rotamer of propiolic acid were obtained.
  • Fundamentals, hot bands, and combination/overtone bands for the trans-conformer were identified.
  • Resonance couplings were observed in trans-propiolic acid dimers and heterodimers with formic acid.
  • A previously unassigned dimer band around 1800 cm⁻¹ was suggested to be a combination of symmetric and antisymmetric OH torsion.

Conclusions:

  • The study provides comprehensive vibrational data for propiolic acid conformers and dimers.
  • The findings offer critical benchmarks for theoretical calculations of molecular vibrational properties.
  • New insights into intermolecular interactions and vibrational couplings in carboxylic acid dimers were gained.