Standard Article

The Chemistry of NO- and HNO-Producing Diazeniumdiolates

Hydroxylamines, Oximes and Hydroxamic Acids (2010)

  1. Anthony S. Evans,
  2. John P. Toscano

Published Online: 15 NOV 2010

DOI: 10.1002/9780470682531.pat0513

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

S. Evans, A. and P. Toscano, J. 2010. The Chemistry of NO- and HNO-Producing Diazeniumdiolates. Patai's Chemistry of Functional Groups. .

Author Information

  1. Johns Hopkins University, Department of Chemistry, Baltimore, Maryland, USA

Publication History

  1. Published Online: 15 NOV 2010

Abstract

Although most diazeniumdiolates (R-N(O)=NO Na+) are stable as solid salts, current interest in their chemistry stems from their ability to produce nitric oxide (NO), nitroxyl (HNO), and/or a mixture of NO and HNO upon decomposition in aqueous solution. Following a discussion concerning the synthesis of diazeniumdiolates, this chapter focuses on how the substituent (R) and experimental conditions influence decomposition chemistry and NO/HNO production. Representative applications of NO- and HNO-producing diazeniumdiolates are also provided.

Keywords:

  • diazeniumdiolate;
  • nitric oxide (NO);
  • nitroxyl (HNO);
  • Angeli’s salt;
  • Cupferron;
  • DEA/NO;
  • IPA/NO