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It is demonstrated that the Cotton effects due to the 220 nm phthalimide π-π* transition observed for a series of derivatives of α-phthalimidocarboxylic acids unequivocally reflect the amino acid absolute configuration. This method is based on the exciton coupling of the allowed transitions of the phthalimide and the carboxylic acid derivative chromophores.
(S,S)-(+)-3,5-Cyclohexadiene-1,2-diol, (S,S)-1, displays positive π-π* Cotton effect, Δ +10.0 at 256 nm in methanol. Variable-temperature CD measurements in alcohol solvent indicate that the conformer with equatorial hydroxy groups is more stable than the diaxial one (ΔG o = 0.71 kcal/mol). The diaxial conformer has one order of magnitude higher rotational strength compared to the diequatorial...
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