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

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Title
The critical size of hydrogen-bonded alcohol clusters as effective Brønsted bases in solutions
Author(s)
Sun-Young Park; Taeg Gyum Kim; Manjaly J. Ajitha; Kijeong Kwac; Young Min Lee; Heesu Kim; Yousung Jung; Oh-Hoon Kwon
Publication Date
2016-09
Journal
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, v.18, no.36, pp.24880 - 24889
Publisher
ROYAL SOC CHEMISTRY
Abstract
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. © 2016 the Owner Societies
URI
https://pr.ibs.re.kr/handle/8788114/2978
ISSN
1463-9076
Appears in Collections:
Center for Soft and Living Matter(첨단연성물질 연구단) > Journal Papers (저널논문)
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