Alcohol Dimer is Requisite to Form an Alkyl Oxonium Ion in the Proton Transfer of a Strong (Photo)Acid to Alcohol |
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| Authors: | Dr Sun‐Young Park Young Min Lee Dr Kijeong Kwac Prof?Dr Yousung Jung Prof?Dr Oh‐Hoon Kwon |
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| Affiliation: | 1. Center for Soft and Living Matter, Institute for Basic Science (IBS), Ulsan, Republic of Korea;2. Department of Chemistry, Ulsan National Institute of Science and Technology (UNIST), Ulsan, Republic of Korea;3. Graduate School of Energy, Environment, Water and Sustainability (EEWS), Korea Advanced Institute of Science and Technology (KAIST), Daejeon, Republic of Korea |
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| 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. |
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| Keywords: | alcohols dehydration hydrogen bonds proton transport time-resolved spectroscopy |
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