Synthesis and structure of 9-hydroxy-1,2-dicarba-closo-dodecaborane(11)
D. A. Rudakov, A. M. Genaev, Yu. V. Gatilov, E. A. Dikusar, T. D. Zvereva, Z. P. Zubreichuk, V. I. Potkin
Российский химический вестник
https://doi.org/10.1007/s11172-020-2763-1
The oxidation of 1,2-C2B10H12 (1) with 100% nitric acid was studied in two solvents (CH2C12 and CCl4). Under the action of superacid (CF3SO3H), the compound 9-HO-1,2-C2B10H11 (2) gives the onium cation 9-H2O+-1,2-C2B10H11 involved in the salt [9-H2O+-1,2-C2B10Hn]-CF3SO3−, as demonstrated by uB NMR spectroscopy. The experimental and simulated uB NMR spectra of the cation 9-H2O+-1,2-C2B10H11 are in satisfactory agreement with each other. In the presence of a base, compound 2 is transferred from an ethereal solution to an aqueous alkaline solution giving the anion 9-O−- 1,2-C2B10H11. The structure of compound 2 was confirmed by 1H, 11B, 11B1H, 11B-11B COSY NMR spectroscopy, IR spectroscopy, and gas chromatography mass spectrometry and was additionally established by X-ray diffraction.
- N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrentieva, 630090, Novosibirsk, Russian FederationD. A. Rudakov, A. M. Genaev & Yu. V. Gatilov
- Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 ul. Surganova, 220072, Minsk, BelarusE. A. Dikusar, T. D. Zvereva, Z. P. Zubreichuk & V. I. Potkin
- L. I. Zakharkin, V. N. Kalinin, L. S. Podvisotskaya, Bull. Acad. Sci. USSR, Div.Chem. Set, 1965, 14, 1684.
- L. I. Zakharkin, V. N. Kalinin, L. S. Podvisotskaya, Zh. Obshch. Khim., 1966, 36, 1786 [J. Gen. Chem. USSR (Engl. Transl.), 1966, 36].
- L. I. Zakharkin, V. N. Kalinin, V. V. Gedymin, Zh. Obshch. Khim., 1970, 40, 2653 [J. Gen. Chem. USSR (Engl. Transl., 1970, 40].
- V. I. Stanko, V. A. Brattsev, V. N. Ovsyannikov, T. P. Klimova, Zh. Obshch. Khim., 1974, 44, 2482 [J. Gen. Chem. USSR (Engl. Transl.), 1974, 44].
- V. A. Brattsev, V. I. Stanko, Zh. Obshch. Khim., 1970, 40, 1664 [J. Gen. Chem. USSR (Engl. Transl.), 1970, 40].
- L. I. Zakharkin, V. N. Kalinin, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1968, 17, 667.
- V. N. Kalinin, L. I. Zakharkin, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1971, 20, 2242.
- K. Nedunchezhian, N. Aswath, M. Thiruppathy, S. Thirugnanamurthy, J. Clin. Diagn. Res., 2016, 10, ZE01.
- S.-I. Miyatake, S. Kawabata, R. Hiramatsu, T. Kuroiwa, M. Suzuki, N. Kondo, K. Ono, Neurol. Med. Chir (Tokyo), 2016, 56, 361.
- E. M. Heber, M. F. Hawthorne, P. J. Kueffer, M. A. Garabalino, S. I. Thorp, E. C. C. Pozzi, A. M. Hughes, C. A. Maitz, S. S. Jalisatgi, D. W. Nigg, P. Curotto, V. A. Trivillin, A. E. Schwint, Proc. Natl. Acad. Sci. USA, 2014, 111, 16077.
- V. I. Bregadze, I. B. Sivaev, Polyhedral Boron Compounds for BNCT, in Boron Science, Ed. N. S. Hosmane, CRC Press, New York, 2012, ch. 9, 181–209.
- I. B. Sivaev, V. I. Bregadze, N. T. Kuznetsov, Russ. Chem. Bull, 2002, 51, 1362.
- S. Gao, Y. Zhu, N. Hosmane, Boron-Based Compounds: Potential and Emerging Applications in Medicine, Eds E. Hey-Hawkins, C. Vifias Teixidor, John Wiley & Sons Ltd., 2018, Ch. 3.4, 371–388.
- J. C. Yanch, S. Shortkroff, R. E. Shefer, S. Johnson, E. Binello, D. Gierga, A. G. Jones, G. Young, C. Vivieros, A. Davison, C. Sledge, Med. Phys., 1999, 26, 364.
- J. F. Valliant, P. Schaffer, J. Inorg. Biochem., 2001, 85, 43.
- V. A. Trivillin, D. B. Abramson, G. E. Bumaguin, L. J. Bruno, M. A. Garabalino, H. A. Monti, E. M. Heber, S. Feldman, A. E. Schwint, Radial Environ. Biophys., 2014, 53, 635.
- T. Base, Z. Bastl, V. Havranek, K. Lang, J. Bould, M. G. S. Londesborough, J. Machacek, J. Plesek, Surface & Coatings Technology, 2010, 204, 2639.
- T. Base, J. Machacek, Z. Hajkova, J. Langecker, J. D. Kennedy, M. J. Carr, J. Organomet. Chem., 2015, 798, 132.
- I. P. Beletskaya, V. I. Bregadze, K. Z. Kabytaev, G. G. Zhigareva, P. V. Petrovskii, I. V. Glukhov, Z. A. Starikova, Organometallics, 2007, 26, 2340.
- D. N. Laikov, Chem. Phys. Lett, 1997, 281, 151.
- D. N. Laikov, Yu. A. Ustynyuk, Russ. Chem. Bull., 2005, 54, 820.
- J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett, 1996, 77, 3865.
- M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347.
- SALNT, v. 6.0, BrukerAXS, Madison, WI, USA.
- SADABS, v. 2008/1, BrukerAXS, Madison, WI, USA.
- G. M. Sheldrick, Acta Cryst., 2015, C71, 3.