Conformational transformations and autooxidation of 5-bromo-2-(2-methylpropyl)-5-nitro-1,3,2-dioxaborinane
- Authors: Valiakhmetova O.Y.1, Tyumkina T.V.2, Meshcheryakova E.S.2, Khalilov L.M.2, Kuznetsov V.V.1,3
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Affiliations:
- Ufa State Petroleum Technological University
- Institute of Petrochemistry and Catalysis
- Ufa State Aviation Technical University
- Issue: Vol 53, No 6 (2017)
- Pages: 926-931
- Section: Article
- URL: https://bakhtiniada.ru/1070-4280/article/view/216415
- DOI: https://doi.org/10.1134/S1070428017060185
- ID: 216415
Cite item
Abstract
Conformational study of 5-bromo-2-(2-methylpropyl)-5-nitro-1,3,2-dioxaborinane at the DFT PBE/3ξ level of theory revealed the only sofa–sofa interconversion pathway through a transition state corresponding to 2,5-twist conformer. The barrier to internal rotation of the axial nitro group is several times higher than that for the equatorial nitro group. According to the 1H, 13C, and 11B NMR, IR, and X-ray diffraction data, the main autooxidation products of 5-bromo-2-(2-methylpropyl)-5-nitro-1,3,2-dioxaborinane are 2-bromo-2-nitropropane-1,3-diol and boric acid.
About the authors
O. Yu. Valiakhmetova
Ufa State Petroleum Technological University
Email: kuzmaggy@mail.ru
Russian Federation, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062
T. V. Tyumkina
Institute of Petrochemistry and Catalysis
Email: kuzmaggy@mail.ru
Russian Federation, pr. Oktyabrya 141, Ufa, Bashkortostan, 450075
E. S. Meshcheryakova
Institute of Petrochemistry and Catalysis
Email: kuzmaggy@mail.ru
Russian Federation, pr. Oktyabrya 141, Ufa, Bashkortostan, 450075
L. M. Khalilov
Institute of Petrochemistry and Catalysis
Email: kuzmaggy@mail.ru
Russian Federation, pr. Oktyabrya 141, Ufa, Bashkortostan, 450075
V. V. Kuznetsov
Ufa State Petroleum Technological University; Ufa State Aviation Technical University
Author for correspondence.
Email: kuzmaggy@mail.ru
Russian Federation, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062; ul. K. Marksa 12, Ufa, Bashkortostan, 450008
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