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Acidity of Carboxylic Acids01:21

Acidity of Carboxylic Acids

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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.
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In titrating a weak acid with a strong base, different calculation methods are applied at various stages. Initially, the pH of a weak acid like acetic acid is calculated using its dissociation constant (Ka) and an ICE table. Upon addition of a strong base such as sodium hydroxide, a buffer forms, and its pH is determined using the Henderson-Hasselbalch equation. As more base is added and the titration reaches the halfway point, the pH becomes equal to the pKa of the acid, indicating equal...
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The pH of a solution containing an acid can be determined using its acid dissociation constant and its initial concentration. If a solution contains two different acids, then its pH can be determined using one of several methods depending upon the relative strength of the acids and their dissociation constants.
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The pH of a solution containing an acid can be determined using its acid dissociation constant and initial concentration. If a solution contains two different acids, then its pH can be determined using one of several methods depending on the relative strength of the acids and their dissociation constants.
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Determination of the Gas-phase Acidities of Oligopeptides
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How Acidic Is Carbonic Acid?

Dina Pines1, Julia Ditkovich1, Tzach Mukra1

  • 1Department of Chemistry, Ben-Gurion University of the Negev , P. O. Box 653, Beer-Sheva 84105, Israel.

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

This study precisely measured the proton transfer rates to determine the acidity of carbonic acid (H2CO3). The findings establish carbonic acid as a significant protonating agent under physiological conditions.

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Area of Science:

  • Physical Chemistry
  • Photochemistry
  • Biophysical Chemistry

Background:

  • Understanding acid-base chemistry is crucial for biological processes.
  • Accurate determination of acid dissociation constants (pK(a)) is essential for predicting chemical behavior.
  • Carbonic acid (H2CO3) plays a vital role in physiological systems, but its precise acidity is debated.

Purpose of the Study:

  • To accurately determine the pK(a) of carbonic acid (H2CO3).
  • To investigate the kinetics of proton transfer reactions between a photoacid and carboxylic acid conjugate bases.
  • To establish the relative acid strengths of carbonic, lactic, and pyruvic acids.

Main Methods:

  • Utilized a tailor-made photoacid (6-hydroxy-1-sulfonate pyrene sodium salt) for transient proton generation.
  • Employed time-correlated single-photon-counting to measure fluorescence lifetimes and derive proton transfer (PT) rates.
  • Applied the Szabo-Collins-Kimball equation to analyze diffusion-assisted PT rates.
  • Used Marcus and Kiefer-Hynes free energy correlations to calculate pK(a).

Main Results:

  • Precisely measured on-contact proton transfer (PT) reaction rates.
  • Observed that PT rates correlate inversely with the acidity of the conjugate bases.
  • Determined the pK(a) of carbonic acid to be 3.49 ± 0.05.
  • Established H2CO3 as 0.37 pK(a) units stronger than lactic acid and 1 pK(a) unit weaker than pyruvic acid.

Conclusions:

  • Carbonic acid (H2CO3) exhibits significant acid strength.
  • The precise pK(a) determination highlights H2CO3's role as an important protonation agent in physiological environments.
  • The study provides a refined understanding of proton transfer kinetics and acid-base equilibria.