A nitric oxide-releasing polydiazeniumdiolate derived from acetonitrile

Org Lett. 2002 Apr 18;4(8):1323-5. doi: 10.1021/ol025624j.

Abstract

Acetonitrile, frequently used as a solvent in reactions of nitric oxide (NO) with amines and other nucleophiles to introduce the [N(O)NO](-) (diazeniumdiolate) functional group, has itself been shown to react with NO in the presence of strong base to yield methane trisdiazeniumdiolate (1), presumably via an intermediate trisdiazeniumdiolated imidate. Aqueous hydrolysis of 1 does not follow simple first-order kinetics and produces mixtures of NO and nitrous oxide in ratios that vary with solution pH. [reaction: see text]

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetonitriles / chemistry*
  • Azo Compounds / chemistry
  • Indicators and Reagents
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Nitric Oxide / chemistry*
  • Reference Standards
  • Solvents
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet

Substances

  • Acetonitriles
  • Azo Compounds
  • Indicators and Reagents
  • Solvents
  • Nitric Oxide