Competitive formation of N-diazeniumdiolates and N-nitrosamines via anaerobic reactions of polyamines with nitric oxide

Org Lett. 2009 Dec 3;11(23):5462-5. doi: 10.1021/ol902282y.

Abstract

Reactions of amines with nitric oxide (NO) at high pressures form diverse NO donor species, highly dependent on the precursor structure. While monoamine precursors favor the formation of N-diazeniumdiolates in high yield, polyamines exhibit competitive formation of N-nitrosamines and diazeniumdiolates, resulting in mixed products containing significant percentages of undesired N-nitroso compounds.

Publication types

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

MeSH terms

  • Amines / chemistry*
  • Azo Compounds / chemical synthesis*
  • Azo Compounds / chemistry
  • Molecular Structure
  • Nitric Oxide / chemistry*
  • Nitric Oxide Donors / chemistry*
  • Nitrosamines / chemical synthesis*
  • Nitrosamines / chemistry
  • Nitroso Compounds / chemical synthesis

Substances

  • Amines
  • Azo Compounds
  • Nitric Oxide Donors
  • Nitrosamines
  • Nitroso Compounds
  • diazeniumdiolate
  • Nitric Oxide