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Synergistic Configuration of Diols as Brønsted Bases

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Title
Synergistic Configuration of Diols as Brønsted Bases
Author(s)
Ye-Jin Kim; Surajit Rakshit; Geun Young Jin; Prasun Ghosh; Young Min Lee; Won-Woo Park; Yung Sam Kim; Oh-Hoon Kwon
Publication Date
2017-12
Journal
CHEMISTRY-A EUROPEAN JOURNAL, v.23, no.68, pp.17179 - 17185
Publisher
WILEY-V C H VERLAG GMBH
Abstract
As viscous hydroxylic organic compounds, diols are of interest for their functional molecular conformation, which is based on inter- and intramolecular hydrogen (H)-bonds. By utilising steady-state electronic and vibrational spectroscopy, time-resolved fluorescence spectroscopy, and computational analyses, we report the association of the hydroxyl groups of diols via intra- or intermolecular H-bonds to enhance their reactivity as a base. Whereas the formation of an intermolecularly H-bonded dimer is requisite for diols of weak intramolecular H-bond to extract a proton from a model strong photoacid, a well-configured single diol molecule with an optimised intramolecular H-bond is revealed to serve as an effective Brønsted base with increased basicity. This observation highlights the collective role of H-bonding in acid–base reactions, and provides mechanistic backgrounds to understand the reactivity of polyols in the acid-catalysed dehydration for the synthesis of cyclic ethers at the molecular level. (c) 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/4222
DOI
10.1002/chem.201703668
ISSN
0947-6539
Appears in Collections:
Center for Soft and Living Matter(첨단연성물질 연구단) > 1. Journal Papers (저널논문)
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