Comparison of the electronic and steric structures of 1-vinyl-and 1-(prop-1-en-1-yl)pyrroles according to the 1H and 13C NMR data View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2007-03

AUTHORS

A. V. Afonin, I. A. Ushakov, D. E. Simonenko, O. A. Tarasova, M. A. Maksimova, B. A. Trofimov

ABSTRACT

According to the 1H and 13C NMR data, 1-isopropenylpyrroles are characterized by larger dihedral angles between the heteroring and exocyclic double bond planes, as compared to isostructural 1-vinylpyrroles, due to steric effect of the α-methyl group in the propenyl fragment. As a result, p-π conjugation with the propenyl group is weaker than with the vinyl group. The propenyl group in 1-isopropenylpyrrole having no other substituents in the heteroring is forced out from the heteroring plane, while the 1-vinylpyrrole molecule is planar. If substituents are present in positions 2 and 5 of the pyrrole ring, the propenyl group on the nitrogen atom becomes orthogonal with respect to the pyrrole ring plane, so that no p-π conjugation is possible. The steric structures of (E)-1-(prop-1-en-1-yl)pyrrole and (Z)-1-(prop-1-en-1-yl)pyrrole are different: the propenyl group in the former is turned relative to the heteroring plane, while the latter molecule is planar. More... »

PAGES

397-405

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428007030116

DOI

http://dx.doi.org/10.1134/s1070428007030116

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1046347133


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