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X-ray crystallographic and C-13 NMR investigations of the effects of electron-withdrawing groups on a series of pyrroles

TitleX-ray crystallographic and C-13 NMR investigations of the effects of electron-withdrawing groups on a series of pyrroles
Publication TypeJournal Article
Year of Publication2000
AuthorsThompson, A, Gao, S, Modzelewska, G, Hughes, DS, Patrick, B, Dolphin, D
JournalOrganic Letters
Volume2
Pagination3587-3590
Date PublishedNov
Type of ArticleArticle
ISBN Number1523-7060
KeywordsDERIVATIVES, NUCLEAR MAGNETIC-RESONANCE, THIOPHENES
Abstract

[GRAPHICS] 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 C-13 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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