Nitrosation by alkyl nitrites. Catalysis by inorganic salts

Isobutyl nitrite is an effective nitrosating agent at acidic, neutral and basic pH in the presence of species arising from phosphate ion. The reaction is first-order in isobutyl nitrite and amine. In the reaction of isobutyl nitrite with sulfanilamide, the pH dependence reflects the change in concentration of the various protonated forms of phosphate, with H3PO4 and H2PO4- most strongly affecting the rate. In the reaction of isobutyl nitrite with dipropylamine, the pH dependence also reflects the change in the concentration of unprotonated amine.