α‐Fluoroalcohols: Synthesis and Characterization of Perfluorinated Methanol, Ethanol and n‐Propanol, and their Oxonium Salts
Abstract
The thermally unstable, primary perfluoroalcohols, CF3OH, C2F5OH, and nC3F7OH, were conveniently prepared from the corresponding carbonyl compounds in anhydrous HF solution. Experimental values for the reaction enthalpies and entropies were derived from the temperature dependence of the RfCOF+HF⇄RfCF2OH (Rf=F, CF3, CF3CF2) equilibria by NMR spectroscopy. Electronic structure calculations of the gas‐phase and solution reaction energies, gas‐phase acidities and heats of formation were carried out at the G3MP2 level, showing that these compounds are strong acids. Protonation of these alcohols in HF/SbF5 produced the perfluoroalkyl oxonium salts RfCF2OH2+SbF6−.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Oct 11, 2018
- Source ID
- 10.1002/chem.201804306
Entities
People
- Amanda F. Baxter
- David A. Dixon
- Joachim Hegge
- Jonas Schaab
- Karl O. Christe
- Monica Vasiliu
- Ralf Haiges
- Thomas Saal
Organizations
- Office of Basic Energy Sciences
- Office of Naval Research
- University of Alabama
- University of Southern California