Egidio Giorgio,Nunziatina Parrinello,Salvatore Caccamese,Carlo Rosini
Organic & Biomolecular Chemistry Pub Date : 11/09/2004 00:00:00 , DOI:10.1039/B411110A
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.

Graphical abstract: 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