Editing Phenol (section)

====Hydrogen bonding====
In [[carbon tetrachloride]] and in alkane solvents, phenol [[hydrogen bonds]] with a wide range of [[Lewis acids and bases|Lewis bases]] such as [[pyridine]], [[diethyl ether]], and [[diethyl sulfide]].  The enthalpies of adduct formation and the {{chem2|\sOH}} IR frequency shifts accompanying adduct formation have been compiled.<ref>Drago, R S. Physical Methods For Chemists, (Saunders College Publishing 1992), ISBN 0-03-075176-4</ref>  Phenol is classified as a [[HSAB theory|hard acid]].<ref>Laurence, C. and Gal, J-F.  Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9</ref><ref>{{cite journal|author1=Cramer, R. E. |author2=Bopp, T. T. |year=1977|title= Graphical display of the enthalpies of adduct formation for Lewis acids and bases |journal= Journal of Chemical Education |volume=54|pages=612–613|doi= 10.1021/ed054p612}} The plots shown in this paper used older parameters. Improved E&C parameters are listed in [[ECW model]].</ref>