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Structure and transformations of diamantane radical cation: Theory and experiment

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Abstract

Quantum chemical calculations at the DFT (B3LYP-D3, M06-2X, B3PW91) and MP2 levels of theory consistently showed that diamantane radical cation in the gas phase has D 3d symmetry with two elongated apical C-H bonds. Its complexation with a nucleophilic solvent stabilizes alternative C s structure with two elongated medial C-H bonds. This is in agreement with the behavior of diamantane under anodic oxidation conditions, which leads to predominant formation of the medial substitution product.

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Authors and Affiliations

  1. “Kyiv Polytechnic Institute” National Technical University of Ukraine, pr. Pobedy 37, Kiev, 03056, Ukraine

    P. A. Gunchenko, A. A. Novikovskii, M. V. Byk & A. A. Fokin

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  1. P. A. Gunchenko
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  2. A. A. Novikovskii
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  3. M. V. Byk
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  4. A. A. Fokin
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Correspondence to A. A. Fokin.

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Original Russian Text © P.A. Gunchenko, A.A. Novikovskii, M.V. Byk, A.A. Fokin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 12, pp. 1768–1773.

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Gunchenko, P.A., Novikovskii, A.A., Byk, M.V. et al. Structure and transformations of diamantane radical cation: Theory and experiment. Russ J Org Chem 50, 1749–1754 (2014). https://doi.org/10.1134/S1070428014120057

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  • DOI: https://doi.org/10.1134/S1070428014120057

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