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

2013 | journal article, A publication of Göttingen

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​From hydrogen bond donor to acceptor: the effect of ethanol fluorination on the first solvating water molecule​
Heger, M.; Scharge, T. & Suhm, M. A. ​ (2013) 
Physical Chemistry Chemical Physics15(38) pp. 16065​-16073​.​ DOI: https://doi.org/10.1039/c3cp53115e 

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Authors
Heger, Matthias; Scharge, Tina; Suhm, Martin A. 
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 center dot center dot center dot 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.
Issue Date
2013
Status
published
Publisher
Royal Soc Chemistry
Journal
Physical Chemistry Chemical Physics 
Organization
Institut für Physikalische Chemie 
ISSN
1463-9084; 1463-9076
Sponsor
DFG (German Research Foundation) [SFB 357, Su121/4]

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