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The intrinsic (gas-phase) acidities of bridgehead alcohols. An experimental (FT-ICR) and computational study

AuthorsHerrero, R.; Dávalos, J.Z. ; Abboud, José Luis M. ; Alkorta, Ibon ; Koppel, I.; Koppel, I. A.; Sonoda, T.; Mishima, M.
Issue Date2007
CitationInternational Journal of Mass Spectrometry 267: 302- 307 (2007)
AbstractThe gas-phase acidities of 1-adamantanol and perfluoro1-adamantanol were determined by means of Fourier transform ion cyclotron resonance spectrometry (FT-ICR). The acidity of perfluoro1-adamantanol seems to be the highest ever reported for an alcohol. A computational study of these species and their anions at both the MP2/6-311 + G(d,p) and B3LYP/6-311 + G(d,p) levels was performed. Also studied were the tertiary alcohols (including their perfluorinated forms) derived from norbornane, bicyclo[2.2.2]octane and cubane. It was found that: (i) the intrinsic acidity of non-fluorinated bridgehead alcohols increases with the strain of the hydrocarbon framework and, (ii) perfluorination of these compounds strongly increases their acidity and, likely, significantly modifies their internal strain. © 2007 Elsevier B.V. All rights reserved.
Identifiersdoi: 10.1016/j.ijms.2007.02.056
issn: 1387-3806
Appears in Collections:(IQM) Artículos
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