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

Authors
Thompson, A Gao, S Modzelewska, G Hughes, DS Patrick, B Dolphin, D
Citation
A. Thompson et al., X-ray crystallographic and C-13 NMR investigations of the effects of electron-withdrawing groups on a series of pyrroles, ORG LETT, 2(23), 2000, pp. 3587-3590
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
23
Year of publication
2000
Pages
3587 - 3590
Database
ISI
SICI code
1523-7060(20001116)2:23<3587:XCACNI>2.0.ZU;2-P
Abstract
[GRAPHICS] A series of pyrroles substituted with various electron-withdrawing groups ( EWGs) on the N atom have been synthesized and full characterization includi ng 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 alterna tive mechanisms of nucleophilic substitution reactions can thus be rational ized.