title: X-ray crystallographic and (13)C NMR investigations of the effects of electron-withdrawing groups on a series of pyrroles
abstract: A series of pyrroles substituted with various electron-withdrawing groups (EWGs) on the N atom have been synthesized and full characterization including X-ray crystal structures obtained. Analysis of (13)C chemical shifts and X-ray crystal structures reveals that a trend between decreased aromaticity and the strength of the EWG exists. Experimental results regarding alternative mechanisms of nucleophilic substitution reactions can thus be rationalized.
authors.affiliation: Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada.
authors.initials: A
authors.lastname: Thompson
authors.initials: S
authors.lastname: Gao
authors.initials: G
authors.lastname: Modzelewska
authors.initials: DS
authors.lastname: Hughes
authors.initials: B
authors.lastname: Patrick
authors.initials: D
authors.lastname: Dolphin