Non-empirical assignment of the absolute configuration of (−)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power

Egidio Giorgio; Nunziatina Parrinello; Salvatore Caccamese; Carlo Rosini

doi:10.1039/B411110A

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Egidio Giorgio,^a Nunziatina Parrinello,^b Salvatore Caccamese*^b and Carlo Rosini*^a

Author affiliations

* Corresponding authors

^a Dipartimento di Chimica, Università della Basilicata, via N. Sauro 85, Potenza, ITALY

^b Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 8, Catania, ITALY
E-mail: rosini@unibas.it
Fax: +39 0971 202223
Tel: +39 0971 202241

Abstract

The non-empirical assignment of the absolute configuration of (−)-naringenin, the aglycone of (−)-naringin, a flavanone glycoside abundant in the albedo of immature grapefruits and showing several interesting biological properties, has been approached by two different methods: (a) the exciton analysis of the circular dichroism (CD) spectrum and (b) the ab initio calculation of the optical rotatory power. Both the methods indicate the configurational correlation (−)/(S), as empirically suggested by Gaffield. A comparison of advantages and limitations of the two methods of analysis is also presented.

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Supplementary files

Calculated (CNDO/S-CI) optical data for 2,4,6-trihydroxyacetophenone. PDF (214K)

Article information

DOI: https://doi.org/10.1039/B411110A
Article type: Paper
Submitted: 28 Jul 2004
Accepted: 28 Sep 2004
First published: 09 Nov 2004

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Org. Biomol. Chem., 2004,2, 3602-3607

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