Structural evidence for the arc-shaped topology of hetero[5]polynorbornanes |
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Authors: | Pavle Tro?elj Anamarija Bri? Yasujiro Murata Davor Margeti? |
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Affiliation: | (1) Laboratory for Physical-Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10001 Zagreb, Croatia;(2) Institute for Chemical Research, Kyoto University, Uji Kyoto, 611-0011, Japan; |
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Abstract: | Two novel polarofacial-[5]-polynorbornanes, O 2 N 2 O 2– and COCOC–, were synthesized by cycloaddition reactions and their molecular and crystal structures were determined. These hetero[5]polynorbornanes posses heteroatoms at the norbornene bridges located at the outer convex surface, whereas functionalities are positioned on the inner concave surface. Molecular structures attest the extent of the curvature of their polycyclic backbone, and established that the COCOC-[5]-polynorbornane possesses more curved topology due to larger steric repulsion of 7-norbornane bridges. These experimental results are in good agreement with computational predictions of geometry. Quantum chemical study has identified lone pair repulsive interactions and steric repulsions of bridges as important factors for determining curvature. |
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