Abstract
A study of the 1 H and 13 C NMR spectra of a l,2-diaryl-3-methyl-4,5-dihydro-lH-imidazolium salt series (1) and a comparison with their 4,5-dihydro-1H-imidazole precursors (2) are presented. Signal assignments follow the analysis of two dimensional HMQC, HMBC, HETCOR, COSY and NOESY spectra. The spectral properties of compounds (1) reflect electronic features of the imidazole ring and correlate directly with the contribution of different mesomeric structures to the stabilization of dihydroimidazolium ions. We also report examples of configurationally stable non-biaryl atropisomers, compounds (1k) and (2k), in which the Ar 1 -N bond is the chiral axis. Thus, the stereochemical features of these compounds are readily evaluated on the basis of their spectroscopic data.
Published Version
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