Conformational study of N-vinyl-2-isopropyl- and N-vinyl-2-cyclopropylpyrroles by1H and13C NMR

A. V. Afonin, M. V. Sigalov, B. A. Trofimov, A. I. Mikhaleva, I. A. Aliev

Research output: Contribution to journalArticlepeer-review

Abstract

In N-vinyl-2-isopropylpyrrole the isopropyl group is in a conformation with the CH3 group in an anti position to the vinyl group. On introducing a substituent at the 3 position of the ring the isopropyl group passes into a gauche and (or) a syn conformation, leading to an increase in the dihedral angle between the plane of the vinyl group and the pyrrole ring. In N-vinyl-2-cyclo-propylpyrrole the cyclopropyl group is 80% in the gauche form, which is attributed to the repulsion between the electrons of the σ-shells of the cyclopropyl and pyrrole fragments.

Original languageEnglish
Pages (from-to)914-921
Number of pages8
JournalBulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume40
Issue number5
DOIs
StatePublished - 1 Jan 1991
Externally publishedYes

ASJC Scopus subject areas

  • General Chemistry

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