oa South African Journal of Chemistry - A coloured spin trap which works as a pH sensor : research article



Nitration of 4-hydroxybenzaldehyde afforded 2,6-dinitro-4-hydroxybenzaldehyde , which in the presence of thionyl chloride is converted to 4-chloro-2,6-dinitrobenzaldehyde . This compound is very reactive towards nucleophiles, and reacts easily with methoxyamine, affording the intermediate 4-aminomethoxy-2,6-dinitrobenzaldehyde . Reaction of with -butylhydroxylamine led to a new spin trap of the nitrone type, namely 4-aminomethoxy-3,5-dinitrophenyl-1--butylnitrone . The spin-trapping capabilities of the new compound have been tested in a classical system, in which short-lived radicals were generated by irradiation. The new compound contains an acidic proton with a pK value of 7.8, and removal of this by a base induces a colour change, from yellow to green-blue. In a similar way, a new stable nitronyl-nitroxide radical has been obtained from the intermediate .


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