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

doi:10.1007/BF00961350

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 journal › Article › peer-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 language	English
Pages (from-to)	914-921
Number of pages	8
Journal	Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume	40
Issue number	5
DOIs	https://doi.org/10.1007/BF00961350
State	Published - 1 May 1991
Externally published	Yes

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Chemistry (all)

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10.1007/BF00961350

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title = "Conformational study of N-vinyl-2-isopropyl- and N-vinyl-2-cyclopropylpyrroles by1H and13C NMR",

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.",

author = "Afonin, {A. V.} and Sigalov, {M. V.} and Trofimov, {B. A.} and Mikhaleva, {A. I.} and Aliev, {I. A.}",

year = "1991",

month = may,

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doi = "10.1007/BF00961350",

language = "English",

volume = "40",

pages = "914--921",

journal = "Russian Chemical Bulletin",

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T1 - Conformational study of N-vinyl-2-isopropyl- and N-vinyl-2-cyclopropylpyrroles by1H and13C NMR

AU - Afonin, A. V.

AU - Sigalov, M. V.

AU - Trofimov, B. A.

AU - Mikhaleva, A. I.

AU - Aliev, I. A.

PY - 1991/5/1

Y1 - 1991/5/1

N2 - 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.

AB - 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.

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VL - 40

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JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

IS - 5

ER -

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

Abstract

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