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Aliphatics vs. aromatics hydration thermodynamics.

Giuseppe Graziano1

  • 1Dipartimento di Scienze Biologiche ed Ambientali, Università del Sannio, Via Port'Arsa, 11-82100, Benevento, Italy. graziano@unisannio.it

Biophysical Chemistry
|July 2, 2004
PubMed
Summary

The hydration difference between benzene and aliphatic hydrocarbons is due to van der Waals forces, not just hydrogen bonds. Benzene

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Area of Science:

  • Physical Chemistry
  • Biophysical Chemistry

Background:

  • Makhatadze and Privalov attributed benzene-water hydration differences to aromatic ring H-bonds.
  • Their proposed thermodynamic features for H-bond formation were deemed physically unreliable.

Purpose of the Study:

  • To propose a microscopic interpretation of hydration thermodynamics for benzene.
  • To re-evaluate the contribution of H-bonds versus van der Waals interactions in benzene hydration.

Main Methods:

  • Statistical mechanical dissection scheme of hydration.
  • Comparison of hydration thermodynamics between benzene and a hypothetical aliphatic hydrocarbon of equal accessible surface area (ASA).

Main Results:

  • The difference in hydration Gibbs energy is attributed to varying van der Waals interactions, driven by benzene's higher polarizability.
  • Differences in hydration entropy reflect distinct water H-bond reorganization upon inserting benzene versus aliphatic hydrocarbons.

Conclusions:

  • Benzene's hydration thermodynamics are better explained by enhanced van der Waals interactions and differential H-bond network reorganization.
  • The role of weak H-bonds in benzene hydration requires re-evaluation based on these findings.

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