The critical size of hydrogen-bonded alcohol clusters as effective Bronsted bases in solutions

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The alkyl oxonium ion, which is a protonated alcohol, has long been proposed as a key reaction intermediate in alcohol dehydration. Nonetheless, the dynamics and structure of this simple but important intermediate species have not been adequately examined due to the transient nature of the oxonium ion. Here, we devised a model system for the key step in the alcohol dehydration reaction, in which a photoacid transfers a proton to alcohols of different basicity in the acetonitrile solvent. Using time-resolved spectroscopy and computation, we have found that the linkage of at least two alcohol molecules via hydrogen bonding is critical for their enhanced reactivity and extraction of the proton from the acid. This finding addresses the cooperative role of the simplest organic protic compounds, namely alcohols, in nonaqueous acid-base reactions
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2016-09
Language
English
Article Type
Article
Keywords

STATE PROTON-TRANSFER; SOLVATION ENERGY RELATIONSHIPS; MOLECULAR-DYNAMICS; ELECTRON-TRANSFER; SUPER PHOTOACIDS; ORGANIC-SOLVENTS; WATER; ACID; DENSITY; SYSTEMS

Citation

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, v.18, no.36, pp.24880 - 24889

ISSN
1463-9076
DOI
10.1039/c6cp01650b
URI
http://hdl.handle.net/10203/213863
Appears in Collection
EEW-Journal Papers(저널논문)
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