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Synthesis, characterization, crystal and molecular structure of 1,5-Dihydro-2H-cyclopenta[1,2-b : 5,4-b ']dipyridin-2-imine

Baysal, Akin
Durap, Feyyaz
Gumgum, Bahattin
Yildirim, Leyla T.
Ulku, Dincer
Boga, Ayse Dilek
Özkar, Saim
The reaction of 1,5-diliydro-2H-cyclopenta[1,2-b:5,4-b'ldipyridin-2-one (3) with an alkylamine (butvlamine, hexylamine or ethylenediamine) yields, quite unexpectedly and in the absence of catalyst, the novel compound 1,5-dihydro-2H-cyclopentafl,2-b:5.4-b']dipyridin-2-imine (4) as the sole, analytically pure, solid product, which was fully characterized. The structure of 4 was unequivocally solved by single-crystal X-ray-diffraction analysis. The compound crystallizes in a monoclinic cell (space group P 2(1/c)). with two molecules in the asymmetric unit. held together by intermolecular H-bonds. Compound 4 could be interesting as a bi- or even tridentate ligand, and exhibits a strong fluorescence upon excitation at 310 nm. A mechanism, based on the observed C-N bond cleavage, is proposed.