Synthesis and reduction kinetics of sterically shielded pyrrolidine nitroxides

Org Lett. 2012 Oct 19;14(20):5322-5. doi: 10.1021/ol302506f. Epub 2012 Oct 10.

Abstract

A series of sterically shielded pyrrolidine nitroxides were synthesized, and their reduction by ascorbate (vitamin C) indicate that nitroxide 3, a tetraethyl derivative of 3-carboxy-PROXYL, is reduced at the slowest rate among known nitroxides, i.e., at a 60-fold slower rate than that for 3-carboxy-PROXYL.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Ascorbic Acid / chemistry
  • Kinetics
  • Models, Molecular
  • Molecular Structure
  • Nitrogen Oxides / chemical synthesis*
  • Oxidation-Reduction
  • Pyrrolidines / chemical synthesis*

Substances

  • Nitrogen Oxides
  • Pyrrolidines
  • nitroxyl
  • pyrrolidine
  • Ascorbic Acid