Acid/base catalysis by pure water: the aldol reaction

J Org Chem. 2005 Nov 25;70(24):9712-6. doi: 10.1021/jo0509455.

Abstract

[reaction: see text] The mechanism of aldol reactions in pure water has been studied with density functional calculations (B3LYP/6-311++G(3d,3p)//B3LYP/6-31G(d)). The reaction is a three-step process that involves: (1) water autoionization generates catalytic hydroxide and hydronium ions, (2) hydroxide and hydronium ions rapidly convert donor aldehyde or ketone into enol, and (3) C-C bond formation and proton transfer occur to give the aldol product. This study provides a general basis for understanding acid/base catalysis by pure water.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Catalysis
  • Crystallography, X-Ray
  • Hydroxides / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Models, Chemical
  • Models, Molecular
  • Molecular Structure
  • Onium Compounds / chemistry*
  • Stereoisomerism
  • Water / chemistry

Substances

  • Aldehydes
  • Hydroxides
  • Ketones
  • Onium Compounds
  • Water
  • hydronium ion
  • hydroxide ion