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Alcohol Dimer is Requisite to Form an Alkyl Oxonium Ion in the Proton Transfer of a Strong (Photo)Acid to Alcohol
Author(s) -
Park SunYoung,
Lee Young Min,
Kwac Kijeong,
Jung Yousung,
Kwon OhHoon
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503948
Subject(s) - oxonium ion , chemistry , protonation , alcohol , alkyl , dissociation (chemistry) , dimer , photochemistry , molecule , cooperativity , solvent , proton , medicinal chemistry , organic chemistry , polymer chemistry , ion , biochemistry , physics , quantum mechanics
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.