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- Title
Alcohol Dimer is Requisite to Form an Alkyl Oxonium Ion in the Proton Transfer of a Strong (Photo)Acid to Alcohol.
- Authors
Park, Sun‐Young; Lee, Young Min; Kwac, Kijeong; Jung, Yousung; Kwon, Oh‐Hoon
- 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.
- Subjects
ALCOHOL research; OXONIUM ions; PROTON transfer reactions; AMPHIPROTIC solvents; CHEMICAL reactions
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 13, p4340
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201503948