Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis

J Org Chem. 2005 Apr 29;70(9):3705-8. doi: 10.1021/jo050161r.

Abstract

[reaction: see text] A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with rho = 1.14 (R(2) = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organo-catalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Indicators and Reagents
  • Kinetics
  • Molecular Structure
  • Nicotine / analogs & derivatives*
  • Nicotine / chemistry*
  • Pyrrolidines / chemical synthesis*
  • Stereoisomerism
  • Water / chemistry

Substances

  • Indicators and Reagents
  • Pyrrolidines
  • Water
  • Nicotine
  • nornicotine