Abstract
ONE of the major problems encountered in using the heavy atom X-ray method1 to determine the structure of steroids2,3 (or any other molecule) is the possibility that the direct attachment of a heavy atom to the molecule will cause distortion. Theoretically, the amount of distortion is determined by steric factors and the stability of the electronic configurations adjacent to the site of attachment. For example, when a bromine atom is covalently attached to carbon four of an aromatic A-ring of the steroid nucleus, it is reasonable to expect that the resulting distortion would be insignificant, because of the stability imparted to the A-ring by the aromatic system. Experimental evidence supporting this expectation was obtained in the molecular-structure determinations of 4-bromoestrone2 and 4-bromoestradiol3. In these brominated steroids, the A-rings are extremely planar (non-planarity coefficients 0.02 Å in both cases) despite the covalently attached bromine.
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EGER, C., NORTON, D. Androgenic Steroid Complexes with p-Bromophenol. Nature 208, 997–999 (1965). https://doi.org/10.1038/208997a0
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DOI: https://doi.org/10.1038/208997a0
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