Alcohol Dimer is Requisite to Form an Alkyl Oxonium Ion in the Proton Transfer of a Strong (Photo)Acid to Alcohol.

Abstract

Alcohols, the simplest amphiprotic organic compounds, can exhibit either acidic or basic behavior by donating or accepting a proton. In this study, proton dissociation of a model photoacid in solution is explored by using time-resolved spectroscopy, revealing quantitatively for the first time that alcohol acts as a Brønsted base because of H-bonded cluster formation to enhance the reactivity. The protonated alcohol cluster, the alkyl oxonium ion, can be regarded as a key reaction intermediate in the well-established alcohol dehydration reaction. This finding signifies, as in water, the cooperativity of protic solvent molecules to facilitate nonaqueous acid-base reactions.

• Authors: Sun-Young Park, Young Min Lee, Kijeong Kwac, Yousung Jung, Oh-Hoon Kwon
• Journal: Chemistry (Weinheim an der Bergstrasse, Germany) (Chemistry) Vol. 22 Issue 13 Pg. 4340-4 (Mar 18 2016) ISSN: 1521-3765 [Electronic] Germany
• PMID: 26757097 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.