Absolute configuration assignment made easier by the VCD of coupled oscillating carbonyls: the case of (−)-propanedioic acids, 2-(2,3)-dihydro-3-oxo-1H-isoindol-1-yl)-1,3-dimethyl ester |
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Authors: | Antonio Massa Paola Rizzo Guglielmo MonacoRiccardo Zanasi |
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Affiliation: | Dipartimento di Chimica e Biologia, Università degli Studi di Salerno, via Giovanni Paolo II 132, 84084 Fisciano (SA), Italy |
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Abstract: | Depending on their relative orientation, coupled oscillating carbonyl groups provide a VCD spectrum with a characteristic CO bond stretching region showing a strong bisignate VCD feature, which can be readily predicted adopting long available semiempirical methods. The extended coupled oscillator (ECO) formalism has been used to assign the absolute configuration of a recently synthesized chiral 3-substituted isoindolinone. The prediction of (S) configuration for the (−) enantiomer has been confirmed by quantum mechanical calculations. |
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Keywords: | Vibrational circular dichroism Absolute configuration Extended coupled oscillator VCD calculation Isoindolinone |
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