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Acidity of hydroxamic acids and amides.

Stanislav Böhm1, Otto Exner

  • 1Institute of Organic Chemistry, Prague Institute of Chemical Technology, 16628 Praha 6, Czech Republic.

Organic & Biomolecular Chemistry
|August 21, 2003
PubMed
Summary

Hydroxamic acids and amides exhibit strong acidity due to anion stabilization, surpassing carboxylic acids. Resonance effects significantly contribute to this enhanced acidity in hydroxamic acids.

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Area of Science:

  • Computational Chemistry
  • Organic Chemistry
  • Acid-Base Chemistry

Background:

  • Hydroxamic acids and amides possess notable acidity.
  • Understanding the electronic factors governing their acidity is crucial.

Purpose of the Study:

  • To analyze the acidity of hydroxamic acids and amides using computational methods.
  • To compare their acidity with that of carboxylic acids and understand the underlying electronic effects.

Main Methods:

  • Isodesmic reactions were employed to study acid and anion formation.
  • Energies were calculated using the B3LYP/AUG-cc-pVTZ//B3LYP/6-311 + G(d,p) level of theory.
  • Computational results were validated against limited experimental data.

Main Results:

  • Both amides and hydroxamic acids show stabilization relative to reference molecules.
  • Their corresponding anions are significantly stabilized, accounting for their acidity.
  • Hydroxamic acids and amides exhibit stronger anion stabilization than carboxylic acids.
  • Resonance effects are more pronounced in hydroxamic acids than in amides or carboxylic acids.

Conclusions:

  • The enhanced acidity of hydroxamic acids and amides is primarily attributed to anion stabilization.
  • Resonance plays a significant role, particularly in hydroxamic acids.
  • The stronger acidity of hydroxamic acids versus amides stems from the inductive effect of the hydroxyl group in the neutral molecule.

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