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- W2066257950 abstract "NMR data of several 4-phenylphenanthrenes (15, 16) have revealed that the crowding in these compounds does not lead to chirality at temperatures as low as −90°. The easy rotation of the phenyl substituent observed by NMR implies that notwithstanding the phenanthrene moiety in average behaves as a planar part the phenyl group does not experience steric hindrance. The analysis of temperature-dependent NMR spectra of several derivatives of 1-phenylbenzo[c]phenanthrenes (17-20) indicated that in these compounds exchange processes do occur. By calculations of the free energies of activation from the NMR data two processes could be distinguished: rotation of the phenyl substituent at one side of the helical benzo[c]phenanthrene moiety, for which ΔGXXXrot , is ca. 13.0kcalmol or slightly larger when bulky substituents are present at C2, and racemisation by a rotation of the phenyl group around the opposite end of the benzo[c]phenanthrene skeleton with simultaneous inversion of the helical conformation. For this process ΔGXXXrac is ca. 16kcalmol. The results have been compared with comparable data of related compounds like 1.8-diphenylnaphthalene, hexahelicene, and 4-methylbenzo[c] phenanthrenes, and gave evidence for the remarkably small, space-demanding properties of the phenyl substituent in these compounds." @default.
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- W2066257950 date "1978-01-01" @default.
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- W2066257950 title "Chirality and conformational changes in 4-phenylphenanthrenes and 1-phenylbenzo[c]phenanthrene derivatives" @default.
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- W2066257950 doi "https://doi.org/10.1016/0040-4020(78)88117-4" @default.
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