Pyrroles from ketoximes and acetylene - V. Study of the transmission of substituent effects in 1-vinyl-2-arylpyrroles by 13C NMR spectroscopy

B. A. Trofimov; M. V. Sigalov; V. M. Bzhezovskii; G. A. Kalabin; S. E. Korostova; A. I. Mikhaleva; L. N. Balabanova

doi:10.1007/BF00481135

Pyrroles from ketoximes and acetylene - V. Study of the transmission of substituent effects in 1-vinyl-2-arylpyrroles by ¹³C NMR spectroscopy

B. A. Trofimov, M. V. Sigalov, V. M. Bzhezovskii, G. A. Kalabin, S. E. Korostova, A. I. Mikhaleva, L. N. Balabanova

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

On the basis of a comparative study and analysis of the chemical shifts in the ¹³C NMR spectra of 1-vinyl-2-arylpyrroles and 3-alkyl-1-vinyl-2-phenylpyrroles, as well as 2-phenyl- and 1-ethyl-2-phenylpyrroles, it was established that the effects of substituents in the investigated series are transmitted via a mechanism involving conjugation and π induction; the conductivity and polarizability of the 2-arylpyrrole system increase when a vinyl group is introduced in the 1 position or, in the case of the 1-vinylpyrrole system, when a phenyl group is introduced in the 2 position; this is due to the increase in the degree of overall conjugation.

Original language	English
Pages (from-to)	626-630
Number of pages	5
Journal	Chemistry of Heterocyclic Compounds
Volume	14
Issue number	6
DOIs	https://doi.org/10.1007/BF00481135
State	Published - 1 Jun 1978
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1007/BF00481135

Cite this

@article{dc733944afac40adbbe946c10b7c22bb,

title = "Pyrroles from ketoximes and acetylene - V. Study of the transmission of substituent effects in 1-vinyl-2-arylpyrroles by 13C NMR spectroscopy",

abstract = "On the basis of a comparative study and analysis of the chemical shifts in the 13C NMR spectra of 1-vinyl-2-arylpyrroles and 3-alkyl-1-vinyl-2-phenylpyrroles, as well as 2-phenyl- and 1-ethyl-2-phenylpyrroles, it was established that the effects of substituents in the investigated series are transmitted via a mechanism involving conjugation and π induction; the conductivity and polarizability of the 2-arylpyrrole system increase when a vinyl group is introduced in the 1 position or, in the case of the 1-vinylpyrrole system, when a phenyl group is introduced in the 2 position; this is due to the increase in the degree of overall conjugation.",

author = "Trofimov, {B. A.} and Sigalov, {M. V.} and Bzhezovskii, {V. M.} and Kalabin, {G. A.} and Korostova, {S. E.} and Mikhaleva, {A. I.} and Balabanova, {L. N.}",

year = "1978",

month = jun,

day = "1",

doi = "10.1007/BF00481135",

language = "English",

volume = "14",

pages = "626--630",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer",

number = "6",

}

TY - JOUR

T1 - Pyrroles from ketoximes and acetylene - V. Study of the transmission of substituent effects in 1-vinyl-2-arylpyrroles by 13C NMR spectroscopy

AU - Trofimov, B. A.

AU - Sigalov, M. V.

AU - Bzhezovskii, V. M.

AU - Kalabin, G. A.

AU - Korostova, S. E.

AU - Mikhaleva, A. I.

AU - Balabanova, L. N.

PY - 1978/6/1

Y1 - 1978/6/1

N2 - On the basis of a comparative study and analysis of the chemical shifts in the 13C NMR spectra of 1-vinyl-2-arylpyrroles and 3-alkyl-1-vinyl-2-phenylpyrroles, as well as 2-phenyl- and 1-ethyl-2-phenylpyrroles, it was established that the effects of substituents in the investigated series are transmitted via a mechanism involving conjugation and π induction; the conductivity and polarizability of the 2-arylpyrrole system increase when a vinyl group is introduced in the 1 position or, in the case of the 1-vinylpyrrole system, when a phenyl group is introduced in the 2 position; this is due to the increase in the degree of overall conjugation.

AB - On the basis of a comparative study and analysis of the chemical shifts in the 13C NMR spectra of 1-vinyl-2-arylpyrroles and 3-alkyl-1-vinyl-2-phenylpyrroles, as well as 2-phenyl- and 1-ethyl-2-phenylpyrroles, it was established that the effects of substituents in the investigated series are transmitted via a mechanism involving conjugation and π induction; the conductivity and polarizability of the 2-arylpyrrole system increase when a vinyl group is introduced in the 1 position or, in the case of the 1-vinylpyrrole system, when a phenyl group is introduced in the 2 position; this is due to the increase in the degree of overall conjugation.

UR - http://www.scopus.com/inward/record.url?scp=34250278969&partnerID=8YFLogxK

U2 - 10.1007/BF00481135

DO - 10.1007/BF00481135

M3 - Article

AN - SCOPUS:34250278969

SN - 0009-3122

VL - 14

SP - 626

EP - 630

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

IS - 6

ER -

Pyrroles from ketoximes and acetylene - V. Study of the transmission of substituent effects in 1-vinyl-2-arylpyrroles by ¹³C NMR spectroscopy

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this