Synthesis, structure, and theoretical calculations of 1h-3,7- difurylcyclopenta[3,4-d]pyridazine

Chad A. Snyder, Nathan C. Tice, Jeremy B. Maddox, Sean Parkin, Aaron W. Daniel, Jaron M. Thomas

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


Treating [M{η5-1,2-C5H3(COC 4H3O)2}(CO)3] (3) (M = Mn, 3A, M = Re, 3B) with excess hydrazine hydrate in methanol afforded the desired 5,6-fused ring pyridazine complexes, [M(CO)3{η5-1,2-C5H 3(CC4H3ON)(CC4H3ON)}] (4) (M = Mn, 4A, M = Re, 4B), in high yield (76%). However, when X-ray crystallographic analysis of the pyridazyl complexes 4A and 4B was attempted, all recrystallization trials led to ligand loss to the 1,2-difurylpyridazine, 1,2-C5H3(CC4H3ONH)(CC 4H3ON) (5). Compound 5 was observed to have a coplanar stacking arrangement in the solid state along the crystallographic b axis. Theoretical calculations performed on compound 5 indicate a high degree of intramolecular electronic delocalization as well intermolecular orbital interaction.

Original languageEnglish
Pages (from-to)1275-1290
Number of pages16
Issue number6
StatePublished - May 26 2011

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry


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