Nitrosative dealkylation of some symmetrical tertiary amines

Brian G. Gowenlock, Roderick J. Hutchison, Janet Little, Josef Pfab

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)


The rates of nitrosodealkylation of several symmetrical tertiary amines R3N including trialkylamines (R = Me, Et, Prn, and Bu n) and substituted trialkylamines (R = C6H 5CH2, triethanolamine, and nitrilotriacetic acid) have been measured in aqueous acetic acid-acetate buffers. The rate of formation of diethylnitrosamine was found to be first order in nitrous acid, triethylamine, and in the hydrogen ion concentration for pH >3.1. Rates increased with decreasing amine basicity. The rate equation was consistent with rapid, reversible nitrosation by nitrous acid or acetyl nitrite and a rate-determining subsequent elimination.

Original languageEnglish
Pages (from-to)1110-1114
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number8
Publication statusPublished - 1979


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