Abstract
By cross-coupling of 2-iodo-polyfluoroanilines with a [AuPPh3NN] complex (where NN is 4,4,5,5- tetramethyl-3-oxide-1-oxyl-2-imidazolin-2-ide) in the presence of [Pd(PPh3)4], nitroxide radicals (2-aminopolyfluorophenyl- 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyls) are synthesized. Their molecular and crystal structures are determined by the X-ray crystallographic analysis. It is shown that in the solid phase there are both intra- and intermolecular hydrogen bonds between NH2 groups and O atoms of paramagnetic fragments, which link the molecules into chains or dimers.
Similar content being viewed by others
References
Nitroxides: Applications in Chemistry, Biomedicine, and Materials Science / Eds. G. I. Likhtenshtein, J. Yamauchi, S. Nakatsuji, A. I. Smirnov and R. Tamura. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co., 2008.
A. Alberti. Nitroxide Radicals and Nitroxide Based High-Spin Systems. Molecules and Radicals, Landolt-Boernstein Series, vol. 26D. Berlin, Heidelberg: Springer-Verlag, 2005.
Nitroxides–theory, experiment and applications / Ed. A. I. Kokorin. Rijeka, Croatia: In Tech, 2012.
Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds / Ed. R. G. Hicks. Chichester. UK: John Wiley and Sons, 2010.
S. Rowen. Concepts and Applied Principles of Nitroxides. NY: Research Press, 2015.
M. Baumgarten. High Spin Molecules Directed Towards Molecular Magnets. Chapter 12. In: EPR of Free Radicals in Solids II. Progress in Theoretical Chemistry and Physics, vol. 25. / Eds. A. Lund and M. Shiotani. Dordrecht: Springer, 2012.
Chemical Science of p-Electron Systems / Eds. T. Akasaka, A. Osuka, S. Fukuzumi, H. Kandori and Y. Aso. Japan: Publisher Springer, 2015.
Molecular magnetism / Eds. K. Itoh and M. Kinoshita. Tokyo: Kodansha & Gordon and Breach, 2000.
E. V. Tretyakov and V. I. Ovcharenko. Russ. Chem. Rev., 2009, 78, 971–1012.
I. Ratera and J. Veciana. Chem. Soc. Rev., 2012, 41, 303–349.
K. Inoue. Metal-Aminoxyl-Based Molecular Magnets. In: p-Electron Magnetism. Structure and Bonding, vol. 100 / Ed. J. Veciana. Berlin, Heidelberg: Springer, 2001, 61–91.
E. Tretyakov, S. Tolstikov, A. Suvorova, A. Polushkin, G. Romanenko, A. Bogomyakov, S. Veber, M. Fedin, D. Stass, E. Reijerse, W. Lubitz, E. Zueva, and V. Ovcharenko. Inorg. Chem., 2012, 51, 9385–9394.
W. Kaszub, A. Marino, M. Lorenc, E. Collet, E. G. Bagryanskaya, E. V. Tretyakov, V. I. Ovcharenko, and M. V. Fedin. Angew. Chem., Intern. Ed., 2014, 53, 10636–10640.
M. V. Fedin, S. L. Veber, E. G. Bagryanskaya, and V. I. Ovcharenko. Coord. Chem. Rev., 2015, 289-290, 341–356.
K. Doi, T. Ishida, and T. Nogami. Chem. Lett., 2003, 32, 544/545.
Patent WO 2006/82400A1.
L. Politanskaya and E. Tretyakov. Synthesis, 2018, 50, 555–564.
L. Yu. Safina, G. A. Selivanova, K. Yu. Koltunov, and V. D. Shteingarts. Tetrahedron Lett., 2009, 50, 5245–5247.
L. V. Politanskaya, I. P. Chuikov, E. A. Kolodina, M. S. Shvartsberg, and V. D. Shteingarts. J. Fluor. Chem., 2012, 135, 97–107.
R. Tanimoto, S. Suzuki, M. Kozaki, and K. Okada. Chem. Lett., 2014, 43, 678–680.
G. M. Sheldrick. SHELX-97. Programs for Crystal Structure Analysis (Release 97-2). University of Göttingen, Germany, 1997.
Bruker AXS Inc. SADABS (Version 2.11). Madison, Wisconsin, USA, 2008.
A. L. Spek. PLATON–A Multipurpose Crystallographic Tool (Version 10M). Utrecht University, Utrecht, The Netherlands, 2003.
A. L. Spek. J. Appl. Crystallogr., 2003, 36, 7–13.
C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, and J. van de Stree. J. Appl. Crystallogr., 2006, 39, 453–457.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © 2018 E. V. Tretyakov, T. V. Makhneva, L. V. Politanskaya, I. Yu. Bagryanskaya, D. V. Stass.
Translated from Zhurnal Strukturnoi Khimii, Vol. 59, No. 3, pp. 712–719, March-April, 2018.
Rights and permissions
About this article
Cite this article
Tretyakov, E.V., Makhneva, T.V., Politanskaya, L.V. et al. Molecular and Crystal Structure of 2-Amino-Polyfluorophenyl-4,4,5,5-Tetramethyl-4,5-Dihydro-1H-Imidazol- 3-Oxide-1-Oxyls. J Struct Chem 59, 689–696 (2018). https://doi.org/10.1134/S0022476618030289
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476618030289