Inductive and resonance effects on the acidities of phenol, enols, and carbonyl alpha-hydrogens

J Org Chem. 2009 Jan 16;74(2):914-6. doi: 10.1021/jo8018736.

Abstract

Inductive effects account for 1/3 of the enhanced acidity of phenol versus cyclohexanol, 2/5 of the enhanced acidity of enol versus methanol, and l/4 of the enhanced acidity of carbonyl alpha-hydrogens versus methane.

MeSH terms

  • Aldehydes / chemistry*
  • Alkenes / chemistry*
  • Gases / chemistry
  • Hydrogen-Ion Concentration
  • Phenol / chemistry*
  • Temperature

Substances

  • Aldehydes
  • Alkenes
  • Gases
  • Phenol