Classification and Determination of N-Nitroso Compounds Based on the Differences in Reactivity to Denitrosating Reagents

Abstract

The denitrosation of eleven N-nitroso compounds was followed by using a modification of the method of Eisenbrand and Preussmann. N-Nitroso compounds (except nitrosamides) whose precursor amines had pK_a values smaller than about 10.7 were found to be denitrosated instantaneously on addition of hydrogen bromide/acetic acid. These easily denitrosatable compounds were determined selectively with hydrogen chloride/acetic acid. The order of increasing difficulty in denitrosation of N-nitroso compounds as judged from the reactivity with the above reagents coincided well with that of pK_a values of the precursor amines.