Dimethylaminopyridine (Nucleophile nitrous)

Dimethylaminopyridine, or DMAP, finds general use in organic synthesis as a "nucleophilic catalyst." Its strongly donating dimethylamine group affords it substantial nucleophilicity.

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The adducts formed by its nucleophilic addition, however, are quite reactive - analogous to an acid chloride - so DMAP can push a reaction along nicely. See the Wikipedia entry for an example mechanism.

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DMAP is one of the better nucleophilic catalysts - it's cheap, readily available, and works. Perhaps the one disadvantage is that it can show up on TLC plates under the UV, so it's best to use a standard dilute solution of DMAP if you're tracking the progress of an unknown reaction.