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Related Experiment Videos

Protonated p-Benzoquinone.

Karl K. Irikura1, Michael Meot-Ner (Mautner), L. Wayne Sieck

  • 1Department of Chemistry and Biochemistry, University of Maryland Baltimore County, Baltimore, Maryland 21228.

The Journal of Organic Chemistry
|May 3, 1996
PubMed
Summary

Protonated p-benzoquinone (pBQ) exhibits aliphatic ketone behavior energetically and structurally. Its proton affinity was experimentally determined to be 801.4 kJ/mol, validated by theoretical calculations.

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The Elusive Antiaromaticity of Maleimides and Maleic Anhydride: Enthalpies of Formation of N-Methylmaleimide, N-Methylsuccinimide, N-Methylphthalimide, and N-Benzoyl-N-methylbenzamide.

The Journal of organic chemistry·1997
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Area of Science:

  • Physical chemistry
  • Computational chemistry
  • Spectroscopy

Background:

  • p-benzoquinone (pBQ) is an important organic compound.
  • Understanding its protonation chemistry is crucial for various chemical applications.
  • Previous studies have not fully elucidated the energetics of protonated pBQ.

Purpose of the Study:

  • To investigate the structure and energetics of protonated p-benzoquinone (pBQ).
  • To determine the experimental proton affinity of pBQ.
  • To compare the protonation behavior of pBQ with related compounds.

Main Methods:

  • High-pressure mass spectrometry was employed to study protonated pBQ.
  • Ab initio calculations were performed to support experimental findings.
  • Bracketing measurements and hydration thermochemistry were utilized to determine proton affinity.

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Main Results:

  • The experimental proton affinity of pBQ was found to be 801.4 +/- 8.9 kJ/mol.
  • Theoretical calculations and comparisons with related compounds supported this value.
  • Protonated pBQ structurally and energetically resembles an aliphatic ketone.
  • The dissociation of the hydrate (pBQH+).(H2O) was characterized.

Conclusions:

  • p-benzoquinone exhibits aliphatic ketone-like behavior upon protonation.
  • The determined proton affinity provides valuable energetic data for pBQ.
  • This study enhances the understanding of quinone chemistry and protonation energetics.