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

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.

SUBMITTER: Coneski PN

PROVIDER: S-EPMC2788003 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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

Coneski Peter N PN Schoenfisch Mark H MH

Organic letters 20091201 23

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. ...[more]

PMID: 19899748

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