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Updated: Apr 20, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Propanoate grafting on (H,OH)-Si(0 0 1)-2 × 1
Fabrice Bournel1, Jean-Jacques Gallet, Ulrich Köhler
1Synchrotron SOLEIL, L'Orme des Merisiers, Saint-Aubin, BP 48, 91192 Gif sur Yvette Cedex, France. Sorbonne Universités, UPMC Univ Paris 06, UMR 7614, Laboratoire de Chimie Physique, Matière et Rayonnement, 11 rue Pierre et Marie Curie, 75231 Paris Cedex, France.
Abstract:
We have examined the reactivity of water-covered Si(0 0 1)-2 × 1, (H,OH)-Si(0 0 1)-2 × 1, with propanoic (C2H5COOH) acid at room temperature. Using a combination of spectroscopic techniques probing the electronic structure (XPS, NEXAFS) and the vibrational spectrum (HREELS), we have proved that the acid is chemisorbed on the surface as a propanoate. Once the molecule is chemisorbed, the strong perturbation of the electronic structure of the hydroxyls, and of their vibrational spectrum, suggests that the molecule makes hydrogen bonds with the surrounding hydroxyls. As we find evidence that surface hydroxyls are involved in the adsorption reaction, we discuss how a concerted or a radical-mediated reaction (involving the surface silicon dangling bonds) could lead to water elimination and formation of the ester.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.