Xanthobilirubic acid and its amides. Synthesis, spectroscopy, and solution structures | Zendy

Lightner D. A. | Zendy; Ma J.S. | Zendy; Adams T. C. | Zendy; Franklin R. W. | Zendy; Landen G. L. | Zendy

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Xanthobilirubic acid and its amides. Synthesis, spectroscopy, and solution structures

Author(s) -

Lightner D. A.,

Ma J.S.,

Adams T. C.,

Franklin R. W.,

Landen G. L.

Publication year - 1984

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570210128

Subject(s) - chemistry , lactam , propanoic acid , amide , pyrrole , intramolecular force , monomer , solvent , nuclear magnetic resonance spectroscopy , medicinal chemistry , stereochemistry , organic chemistry , polymer

Xanthobilirubic acid, 5‐[1,5‐didehydro‐3‐ethyl‐4‐methyl‐5‐oxo‐2 H ‐pyrrol‐2‐ylidene)methyl]‐2,4‐dimethyl‐1 H ‐pyrrol‐3‐propanoic acid, its methyl ester, amide, N ‐methylamide and dimethylamide, and kryptopyrromethenone have been synthesized and characterized spectroscopically. In d 6 ‐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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