Journal
INORGANIC CHEMISTRY
Volume 57, Issue 8, Pages 4270-4276Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.inorgchem.7b02767
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Funding
- Research Council of Norway [231086, 262229]
- DOE Office of Science User Facility [DE-AC02-05CH11231]
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Halterman corroles have been synthesized for the first time from pyrrole and Halterman's aldehyde via Gryko's water-methanol method. These were derivatized to the corresponding copper complexes and subsequently to the beta-octabromo complexes. Electronic circular dichroism spectra were recorded for the enantiopure copper complexes, affording the first such measurements for the inherently chiral Cu corrole chromophore. Interestingly, for a given configuration of the Halterman substituents, X-ray crystallographic studies revealed both P and M conformations of the Cu-corrole core, proving that the substituents, even in conjunction with beta-octabromination, are unable to lock the Cu-corrole core into a given chirality. The overall body of evidence strongly indicates a dynamic equilibrium between the P and M conformations. Such an interconversion, which presumably proceeds via saddling inversion, provides a rationale for our failure so far to resolve sterically hindered Cu corroles into their constituent enantiomers by means of chiral HPLC.
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