Conformational study of 2-arylazo-1-vinylpyrroles

Conformational study of 2‐phenylazo‐1‐vinylpyrrole and 2‐(4‐bromophenyl)azo‐5‐methyl‐1‐vinylpyrrole was performed on the basis of the experimental measurements and high‐level ab initio calculations of their 13C13C and 13C1H spin–spin coupling constants, showing marked stereochemical behaviour upon...

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Published in:Magnetic resonance in chemistry 2007-02, Vol.45 (2), p.142-151
Main Authors: Rusakov, Yury Yu, Krivdin, Leonid B., Senotrusova, Elena Yu, Schmidt, Elena Yu, Vasiltsov, Alexander M., Mikhaleva, Albina I., Trofimov, Boris A., Dyachenko, Oleg A., Chekhlov, Anatolii N., Kazheva, Olga N.
Format: Article
Language:English
Subjects:
13C NMR
2-arylazo-1-vinylpyrroles
conformational analysis
lone-pair effect
NMR
SOPPA
spin-spin coupling constant
X ray
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Summary:Conformational study of 2‐phenylazo‐1‐vinylpyrrole and 2‐(4‐bromophenyl)azo‐5‐methyl‐1‐vinylpyrrole was performed on the basis of the experimental measurements and high‐level ab initio calculations of their 13C13C and 13C1H spin–spin coupling constants, showing marked stereochemical behaviour upon the internal rotation of the vinyl group and the pyrrolyl moiety. In liquid phase, both compounds were found to adopt predominant s‐trans‐s‐trans conformation with the noticeable population (ca. 30%) of the higher‐energy s‐cis‐s‐trans conformation in the latter compound. As follows from the X‐ray data, 2‐phenylazo‐1‐vinylpyrrole crystallizes in s‐trans‐s‐trans conformation while the crystalline molecular structure of 2‐(4‐bromophenyl)azo‐5‐methyl‐1‐vinylpyrrole is s‐cis‐s‐trans. Copyright © 2006 John Wiley & Sons, Ltd.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.1934