Absolute configuration assignment of inherently chiral calix[4]arenes using DFT calculations of chiroptical properties.
The racemate of an inherently chiral meta-substituted calix[4]arene derivative 3 has been resolved via enantioselective HPLC. Measured optical rotation dispersion and electronic circular dichroism have been compared with DFT theoretical predictions. The comparison indicates that the absolute configuration of the dextrorotatory enantiomer (+)-3 is cS. The procedure has been successfully tested against a literature precedent confirming the validity of the method.
Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, I-84084 Fisciano (Salerno), Italy.
Carmen
C
Talotta
Carmine
C
Gaeta
Francesco
F
Troisi
Guglielmo
G
Monaco
Riccardo
R
Zanasi
Giuseppe
G
Mazzeo
Carlo
C
Rosini
Placido
P
Neri
D047250:Calixarenes / Q000737:chemistry*; D003198:Computer Simulation; D008956:Models, Chemical; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
D010636:Phenols; C121325:calix(4)arene; D047250:Calixarenes