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Structure of tetrahydro-2-naphthyl-4H-1,3,6,2-dioxazaboracine

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Abstract

Intramolecular B-N coordination occurs in tetrahydro-2-naphthyl-4H-1,3,6,2-dioxazaboracine, 2: (R = 2-naphthyl; R′ = H) both in the solid state and in CDCl3 solution. Compound 2: (R = 2-naphthyl; R′ = H) crystallizes in the orthorhombic space group P212121 (Z = 4), with a = 9.266(6), b = 11.034(8), c = 12.0635(10) Å. Molecules are linked, in the solid state, into spiral chains. As only one of the two oxygen atoms present in each molecule is involved in H-bonding, the boron and nitrogen centres are chiral. The intramolecular B-N bond length is 1.671(4) Å; other geometric parameters are B-O bond lengths of 1.448(4) and 1.464(4) Å, a B-C bond length of 1.598(4) Å, and bond angles at B between 100.6(3) and 115.4(3)°. The δ11B value for 2 (R = 2-naphthyl, R′ = H) at 25°C in CDCl3 solution is 10.7 ppm.

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Authors and Affiliations

  1. School of Applied Sciences, The Robert Gordon University, St. Andrews St. Aberdeen, AB25 1HG, Scotland

    Solange M. S. V. Doidge-Harrison

  2. Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland

    Oliver C. Musgrave & James L. Wardell

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  1. Solange M. S. V. Doidge-Harrison
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  2. Oliver C. Musgrave
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  3. James L. Wardell
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Doidge-Harrison, S.M.S.V., Musgrave, O.C. & Wardell, J.L. Structure of tetrahydro-2-naphthyl-4H-1,3,6,2-dioxazaboracine. Journal of Chemical Crystallography 28, 361–366 (1998). https://doi.org/10.1023/A:1022460124784

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