Restricted Rotation in 9-Phenyl-anthracenes: A Prediction Fulfilled
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The calculated phenyl rotation barrier in 9-phenylanthracene has been reported as ~21 kcal mol(-1), but experimental verification of this barrier is limited by its intrinsic symmetry. V-T NMR indicated the barrier to interconversion of the syn (C(2v)) and anti (C(2h)) rotamers of 9,10-bis(3-fluorophenyl)anthracene to be ~21 kcal mol(-1). Likewise, the V-T NMR spectra of 9-(1-naphthyl)-10-phenylanthracene reveal that the rotational barrier of the unsubstituted phenyl ring is at least 21 kcal mol(-1).
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