Collect. Czech. Chem. Commun. 1993, 58, 77-81

Effect of the π-Electron Ring Current on the 1H NMR Spectra of 1,1'-Binaphthol Derivatives

Gustavo Marin-Pugaa, Václav Horákb and Paris Svornosc

a Chemistry Department, Universidad Catolica del Norte, Antofagasta, Chile
b Chemistry Department, Georgetown University, Washington DC20057, U.S.A.
c Chemistry Department, Queensborough College of the City University Of New York, Bayside NY 11364, U.S.A.


High resolution 1H NMR spectra of two 1,1'-binaphthols (I, II), two 1,1'-binaphthalenediols (III, IV) and four 1,1'- binaphthalenediols acetates (IIIa - IVa) were obtained and analyzed. The effect of the ring current was evaluated by comparing the chemical shifts of the compounds, assigned through H-H COSY NMR experiments, to those of the corresponding monomers. All experimental chemicals shifts are in close agreement with the theoretical values obtained via the Bovey model for the ring current effect of a benzene moiety.