X-ray crystallographic and (13)C NMR investigations of the effects of electron-withdrawing groups on a series of pyrroles |
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| Authors: | Thompson Gao Modzelewska Hughes Patrick Dolphin |
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| Affiliation: | Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada. |
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| 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. |
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