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Intramolecular interactions in N-vinyl-2-arylpyrroles and -2-heteroarylpyrroles by 1H and 13C NMR

✍ Scribed by Andrei V. Afonin; Mark V. Sigalov; Svetlana E. Korostova; Ismail A. Aliev; Alexander V. Vashchenko; Boris A. Trofimov

Book ID
102951430
Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
587 KB
Volume
28
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The introduction of a substituent in the 3‐position of the pyrrole ring in N‐vinyl‐2‐arylpyrroles and ‐2‐heteroarylpyrroles results in an increase in the dihedral angles between the planes of the pyrrole ring and the aryl (or heteroaryl) residue, and a decrease in the dihedral angle between the planes of the pyrrole ring and the vinyl group. Introduction of the substituent in the 5‐position of the pyrrole ring has the opposite effect on these angles. For N‐vinyl‐2‐(2′‐furyl)pyrrole, some spectral data suggest the formation of a CH…O hydrogen bond between the α‐hydrogen atom of the vinyl group and the oxygen atom of the furyl ring. This is in accord with the results of quantum chemical calculations.

📜 SIMILAR VOLUMES

C—H···X (X = N, O, S) intramolecular int
C—H···X (X = N, O, S) intramolecular interaction in 1-vinyl-2-(2′-heteroaryl)pyrroles as monitored by 1H and 13C NMR spectroscopy
✍ Andrei V. Afonin; Igor A. Ushakov; Svetlana Yu. Kuznetsova; Ol'ga V. Petrova; El 📂 Article 📅 2002 🏛 John Wiley and Sons 🌐 English ⚖ 147 KB

## Abstract ^1^H and ^13^C NMR spectroscopy of a series of 1‐vinyl‐2‐(2′‐heteroaryl)‐pyrroles were employed for the analysis of their electronic and spatial structure. The C—H···N intramolecular interaction between the α‐hydrogen of the vinyl group and the pyridine nitrogen, a kind of hydrogen bond