Nuclear magnetic resonance spectra of the epihalohydrins: II. Spectral analyses and structural correlations for all the epihalohydrins

Abstract

Complete analyses of the proton magnetic resonance spectra of propylene oxide, epifluorohydrin, epibromohydrin, and epiiodohydrin shows that in all cases the cisoid coupling constants over four bonds are negative, and the transoid coupling constants positive. Dipole moments, together with the vicinal coupling constants of the CH—CH₂X moiety, are used to establish the probable conformations for all the epihalohydrins. Conformational factors appear to obscure any possible relationship between substituent electronegativity and long-range coupling constants.