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

dc.contributor.authorHeger, Matthias
dc.contributor.authorScharge, Tina
dc.contributor.authorSuhm, Martin A.
dc.date.accessioned2014-06-10T10:17:53Z
dc.date.available2014-06-10T10:17:53Z
dc.date.issued2013-10-14
dc.identifier.citationHeger, Matthias; Scharge, Tina; Suhm, Martin A (2013): From hydrogen bond donor to acceptor: the effect of ethanol fluorination on the first solvating water molecule. - Physical chemistry chemical physics : PCCP, Vol. 15, Nr. 38, p. 16065-73
dc.relation.ISSN1463-9084
dc.identifier.urihttp://resolver.sub.uni-goettingen.de/purl?gs-1/10178
dc.description.abstractSupersonic 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.
dc.languageeng
dc.language.isoeng
dc.rightsopenAccess
dc.subjectethanol fluorination; solvating water molecule; hydrogen bond donor
dc.titleFrom hydrogen bond donor to acceptor: the effect of ethanol fluorination on the first solvating water molecule.
dc.typejournalArticle
dc.identifier.doi10.1039/c3cp53115e
dc.type.versionpublishedVersion
dc.identifier.fs597485
dc.bibliographicCitation.volume15
dc.bibliographicCitation.issue38
dc.bibliographicCitation.firstPage16065
dc.bibliographicCitation.lastPage16073
dc.type.subtypejournalArticle
dc.identifier.pmid23965951
dc.notesThis publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively.
dc.description.statuspeerReviewed
dc.bibliographicCitation.journalPhysical chemistry chemical physics : PCCP


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