Pub No:
370
Title:
X-ray Crystallographic and 13C NMR Investigations of the Effects of Electron Withdrawing Groups on a Series of Pyrroles
Authors:
Thompson, A., Gao, S., Modzeleweska, G., Hughes, D.S., Patrick, B., and David Dolphin
Journal:
Org. Lett
Year:
2000
Pages:
3587-3590
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 13C 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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