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Issue 38, 2013
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From hydrogen bond donor to acceptor: the effect of ethanol fluorination on the first solvating water molecule

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Abstract

Supersonic jet FTIR spectra of the OH stretching vibrations in complexes of mono-, di- and trifluoroethanol with water are presented. In contrast to the non-fluorinated ethanol case, the fluorinated alcohols are all shown to act as O–H⋯O hydrogen bond donors towards water. This is found to be mostly a consequence of the intramolecular electron-withdrawing effect of the fluorine atoms and, with decreasing importance for increasing fluorination, due to the attractive intermolecular contact between one of the dangling water OH groups and the fluorine atoms. The findings provide a stepwise rationalization for the hydrophobic properties of the pharmaceutically important trifluoromethyl group.

Graphical abstract: From hydrogen bond donor to acceptor: the effect of ethanol fluorination on the first solvating water molecule

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Publication details

The article was received on 29 Jul 2013, accepted on 05 Aug 2013 and first published on 22 Aug 2013


Article type: Paper
DOI: 10.1039/C3CP53115E
Citation: Phys. Chem. Chem. Phys., 2013,15, 16065-16073

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    From hydrogen bond donor to acceptor: the effect of ethanol fluorination on the first solvating water molecule

    M. Heger, T. Scharge and M. A. Suhm, Phys. Chem. Chem. Phys., 2013, 15, 16065
    DOI: 10.1039/C3CP53115E

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