Abstract
A yellow tripyrrole analog (1) of bilirubin has been synthesized, and its lone propionic acid group is found to engage in conformation determining, intramolecular hydrogen bonding in solution and in the crystal. Molecular modelling and X-ray crystallography reveal an abbreviated ridge-tile or L-shape conformation in which an essentially planar dipyrrinone is hydrogen bonded to the single opposing propionic acid group. In the (arbitrary) (P)-helicity ridge-tile, the torsion angles about C(10) are computed to be 55° and 61° by molecular dynamics and found to be 66° and 53° in the crystal. Such torsion angles lead to an interplanar dihedral angle (∼93°) between the dipyrrinone and its adjoining pyrrole that is very close to the dihedral angle (∼98°) found in intramolecularly hydrogen bonded bilirubin.
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