title: 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.
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.
authors.affiliation: Dipartimento di Chimica, Università della Basilicata, via N. Sauro 85, 85100, Potenza, Italy.
authors.forename: Egidio
authors.initials: E
authors.lastname: Giorgio
authors.forename: Nunziatina
authors.initials: N
authors.lastname: Parrinello
authors.forename: Salvatore
authors.initials: S
authors.lastname: Caccamese
authors.forename: Carlo
authors.initials: C
authors.lastname: Rosini
mesh_terms: D002942:Circular Dichroism; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009904:Optical Rotation; D013237:Stereoisomerism
chemical_list: D044950:Flavanones; C005273:naringenin