Conformational rigidity and flexibility of the paracyclophane skeleton in substituted [2.2]paracyclophanes View Full Text


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Article Info

DATE

2004-09

AUTHORS

Z. A. Starikova, I. V. Fedyanin, M. Yu. Antipin

ABSTRACT

The character of distortions of the paracyclophane skeleton in various substituted [2.2]paracyclophanes was analyzed based on X ray diffraction data. The rigidity of the skeleton is provided by ethylene bridges and flexibility of the benzene rings, which adopt a boat conformation. The flexibility of the skeleton is manifested in the displacement of the benzene rings with respect to each other and conformational changes of ethylene bridges. The changes in these characteristics are very sensitive to intra- and intermolecular steric factors and are indicative of the absence of strong specific stacking interactions between the be nzene rings. Precision X-ray diffraction study and quantum-chemical calculations for unsubstituted [2.2]paracyclophane and 4,7-benzoquinono[2.2]paracyclophane demonstrated that there are no attractive interactions between the benzene rings, and the electron density is localized predominantly on the outer surface of the rings. This fact can be considered as the “cage molecular” effect of the [2.2]paracyclophane skeleton. More... »

PAGES

1779-1805

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-005-0039-4

DOI

http://dx.doi.org/10.1007/s11172-005-0039-4

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1045327602


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58 schema:description The character of distortions of the paracyclophane skeleton in various substituted [2.2]paracyclophanes was analyzed based on X ray diffraction data. The rigidity of the skeleton is provided by ethylene bridges and flexibility of the benzene rings, which adopt a boat conformation. The flexibility of the skeleton is manifested in the displacement of the benzene rings with respect to each other and conformational changes of ethylene bridges. The changes in these characteristics are very sensitive to intra- and intermolecular steric factors and are indicative of the absence of strong specific stacking interactions between the be nzene rings. Precision X-ray diffraction study and quantum-chemical calculations for unsubstituted [2.2]paracyclophane and 4,7-benzoquinono[2.2]paracyclophane demonstrated that there are no attractive interactions between the benzene rings, and the electron density is localized predominantly on the outer surface of the rings. This fact can be considered as the “cage molecular” effect of the [2.2]paracyclophane skeleton.
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