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

…, DE Simonenko, OA Tarasova, MA Maksimova…

Index: Afonin; Ushakov; Simonenko; Tarasova; Maksimova; Trofimov Russian Journal of Organic Chemistry, 2007 , vol. 43, # 3 p. 397 - 405

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Citation Number: 4

Abstract

Abstract According to the 1 H and 13 C 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 ...