Xanthobilirubic acid and its amides. Synthesis,spectroscopy, and solution structures |
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| Authors: | D A Lightner J-S Ma T C Adams R W Franklin G L Landen |
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| Institution: | Department of Chemistry, University of Nevada, Reno, Nevada 89557 |
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| Abstract: | Xanthobilirubic acid, 5-1,5-didehydro-3-ethyl-4-methyl-5-oxo-2H-pyrrol-2-ylidene)methyl]-2,4-dimethyl-1H-pyrrol-3-propanoic acid, its methyl ester, amide, N-methylamide and dimethylamide, and kryptopyrromethenone have been synthesized and characterized spectroscopically. In d6-DMSO solution all pyrromethenones were monomeric, with lactam and pyrrole N-Hs H-bonded to solvent. In deuteriochloroform, the pyrromethenones preferred a dimeric form, with intramolecular H-bonding between the lactam C = 0 of one unit and the lactam and pyrrole N-Hs of the second. |
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