Nitrosative dealkylation of some symmetrical tertiary amines

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

Nitrosative dealkylation of some symmetrical tertiary amines

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

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

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 language	English
Pages (from-to)	1110-1114
Number of pages	5
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	8
Publication status	Published - 1979

Cite this

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title = "Nitrosative dealkylation of some symmetrical tertiary amines",

abstract = "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.",

author = "Gowenlock, {Brian G.} and Hutchison, {Roderick J.} and Janet Little and Josef Pfab",

year = "1979",

language = "English",

pages = "1110--1114",

journal = "Journal of the Chemical Society, Perkin Transactions 2",

issn = "1472-779X",

publisher = "Royal Society of Chemistry",

number = "8",

}

TY - JOUR

T1 - Nitrosative dealkylation of some symmetrical tertiary amines

AU - Gowenlock, Brian G.

AU - Hutchison, Roderick J.

AU - Little, Janet

AU - Pfab, Josef

PY - 1979

Y1 - 1979

N2 - 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.

AB - 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.

M3 - Article

SN - 1472-779X

SP - 1110

EP - 1114

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

IS - 8

ER -

Nitrosative dealkylation of some symmetrical tertiary amines

Abstract

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