Proton transfer reactions between nitric acid and acetone, hydroxyacetone, acetaldehyde and benzaldehyde in the solid phase

Phys Chem Chem Phys. 2012 Dec 5;14(45):15715-21. doi: 10.1039/c2cp42033c. Epub 2012 Oct 23.

Abstract

The heterogeneous and homogeneous reactions of acetone, hydroxyacetone, acetaldehyde and benzaldehyde with solid nitric acid (HNO(3)) films have been studied with Reflection-Absorption Infrared Spectroscopy (RAIRS) under Ultra-High Vacuum (UHV) conditions in the 90-170 K temperature range. In the bulk or at the surface of the films, nitric acid transfers its proton to the carbonyl function of the organic molecules, producing protonated acetone-H(+), hydroxyacetone-H(+), acetaldehyde-H(+) and benzaldehyde-H(+), and nitrate anions NO(3)(-), a reaction not observed when nitric acid is previously hydrated [J. Lasne, C. Laffon and Ph. Parent, Phys. Chem. Chem. Phys., 2012, 14, 697]. This provides a molecular-scale description of the carbonyl protonation reaction in an acid medium, the first step of the acid-catalyzed condensation of carbonyl compounds, fuelling the growth of secondary organic aerosols (SOA) in the atmosphere.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaldehyde / chemistry*
  • Acetone / analogs & derivatives
  • Acetone / chemistry*
  • Benzaldehydes / chemistry*
  • Nitric Acid / chemistry*
  • Protons*
  • Spectroscopy, Fourier Transform Infrared
  • Temperature

Substances

  • Benzaldehydes
  • Protons
  • Acetone
  • Nitric Acid
  • Acetaldehyde
  • benzaldehyde