Where did all the bpy go? - Synthesis, crystal and molecular structure of 4-nitropicolinic acid monohydrate

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The conversion of 2,2-bipyridine (bpy) to 4,4'-disubstituted derivatives is commonly achieved by a route involving preparation of the NAP-dioxide and subsequent nitration with HNO3/H2SO4. The yields in the latter reaction are of the order of 50% and we now show that a competing ring oxidation process leads to the formation of 4-nitropicolinic acid. The solid state structure of the monohydrate of 4-nitropicolinic acid is reported, which exhibits a series of interesting packing motifs arising from hydrogen bonding networks.


Original languageEnglish
Pages (from-to)299-303
Number of pages5
JournalSupramolecular Chemistry
Issue number4
Publication statusPublished - 1 Apr 2006


  • nitration, 2,2-bipyridine, oxidation, crystal structure