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Structural evidence for the arc-shaped topology of hetero[5]polynorbornanes

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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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Acknowledgments

Financial support of the Ministry of science, education and sport of Croatia (projects No. 098-0982933-3218 and 098-0982933-2920) is gratefully acknowledged.

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Authors and Affiliations

  1. Laboratory for Physical-Organic Chemistry, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10001, Zagreb, Croatia

    Pavle Trošelj, Anamarija Briš & Davor Margetić

  2. Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011, Japan

    Yasujiro Murata

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  1. Pavle Trošelj
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  2. Anamarija Briš
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  3. Yasujiro Murata
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  4. Davor Margetić
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Correspondence to Davor Margetić.

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Trošelj, P., Briš, A., Murata, Y. et al. Structural evidence for the arc-shaped topology of hetero[5]polynorbornanes. Struct Chem 23, 791–799 (2012). https://doi.org/10.1007/s11224-011-9925-6

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  • DOI: https://doi.org/10.1007/s11224-011-9925-6

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