Abstract
New bis-p-iminobenzoquinone ligands, in which two hydroxy-p-iminobenzoquinone moieties are bridged by various functionalized linkers, were synthesized by 1,4-addition of aromatic diamines to 3,6-di-tert-butyl-o-benzoquinone. The exchange reaction between potassium salts of new ligands and ethylmercury(ii) chloride produces the corresponding mono- and binuclear metal complexes. In these complexes, the mercury atoms exhibit T-shaped trigonal geometry characteristic of three-coordinate mercury(ii) derivatives. The structures of the new ligands and the mercury complexes with these ligands were determined by IR, UV, and NMR spectroscopy and X-ray diffraction.
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V. P. Ananikov, L. L. Khemchyan, Yu. V. Ivanova, V. I. Bukhtiyarov, A. M. Sorokin, I. P. Prosvirin, S. Z. Vatsadze, A. V. Medved’ko, V. N. Nuriev, A. D. Dilman, V. V. Levin, I. V. Koptyug, K. V. Kovtunov, V. V. Zhivonitko, V. A. Likholobov, A. V. Romanenko, P. A. Simonov, V. G. Nenajdenko, O. I. Shmatova, V. M. Muzalevskiy, M. S. Nechaev, A. F. Asachenko, O. S. Morozov, P. B. Dzhevakov, S. N. Osipov, D. V. Vorobyeva, M. A. Topchiy, M. A. Zotova, S. A. Ponomarenko, O. V. Borshchev, Yu. N. Luponosov, A. A. Rempel, A. A. Valeeva, A. Yu. Stakheev, O. V. Turova, I. S. Mashkovsky, S. V. Sysolyatin, V. V. Malykhin, G. A. Bukhtiyarova, A. O. Terent’ev, I. B. Krylov, Russ. Chem. Rev., 2014, 83, 885.
K. S. Min, A. G. DiPasquale, A. L. Rheingold, J. S. Miller, Inorg. Chem., 2007, 46, 1048.
S. Kanegawa, Y. Shiota, S. Kang, K. Takahashi, H. Okajima, A. Sakamoto, T. Iwata, H. Kandori, K. Yoshizawa, O. Sato, J. Am. Chem. Soc., 2016, 138, 14170.
N. Ch. Jana, P. Brandao, C. Mathoniere, A. Panja, Polyhedron, 2018, 144, 152.
A. G. Starikov, А. А. Tsaturyan, А. А. Starikova, E. А. Gusakov, V. I. Minkin, Russ. Chem. Bull., 2018, 67, 1182.
A. G. Starikov, A. A. Starikova, M. G. Chegerev, V. I. Minkin, Russ. J. Coord. Chem., 2019, 45, 105.
D. M. D’Alessandro, Chem. Commun., 2016, 52, 8957.
S. Kitagawa, S. Kawata, Coord. Chem. Rev., 2002, 224, 11.
A. Abherve, M. Clemente-Leon, E. Coronado, C. J. Goomez-Garcia, M. Verneret, Inorg. Chem., 2014, 53, 12014.
A. Abherve, S. Manas-Valero, M. Clemente-Leon, E. Coronado, Chem. Sci., 2015, 6, 4665.
M. N. Leuenberger, D. Loss, Nature, 2001, 410, 789.
K. Senthil Kumar, M. Ruben, Coord. Chem. Rev., 2017, 346, 176.
C. Janiak, Dalton Trans., 2003, 2781.
Z. Hu, B. J. Deibert, J. Li, Chem. Soc. Rev., 2014, 43, 5815.
L.-J. Xu, G.-T. Xu, Z.-N. Chen, Coord. Chem. Rev., 2014, 273-274, 47.
Y. Cui, B. Chen, G. Qian, Coord. Chem. Rev., 2014, 273-274, 76.
L. Sun, M. G. Campbell, M. Dinca, Angew. Chem., Int. Ed., 2016, 55, 3566.
S. A. Sapchenko, D. N. Dybtsev, V. P. Fedin, Pure Appl. Chem., 2017, 89, 1049.
D. N. Dybtsev, A. A. Sapianik, V. P. Fedin, Mendeleev Commun., 2017, 27, 321.
G. M. Espallargas, E. Coronado, Chem. Soc. Rev., 2018, 47, 533.
M. O. Barsukova, S. A. Sapchenko, D. N. Dybtsev, V. P. Fedin, Russ. Chem. Rev., 2018, 87, 1139.
A. A. Simagina, M. V. Polynski, A. V. Vinogradov, E. A. Pidko, Russ. Chem. Rev., 2018, 87, 831.
M. G. Chegerev, A. V. Piskunov, Russ. J. Coord. Chem., 2018, 44, 305.
K. V. Tsys, M. G. Chegerev, G. K. Fukin, A. V. Piskunov, Mendeleev Commun., 2018, 28, 527.
G. A. Abakumov, V. I. Nevodchikov, N. V. Zaitova, N. O. Druzhkov, L. G. Abakumova, Yu. A. Kurskii, V. K. Cherkasov, Russ. Chem. Bull., 1997, 46, 2093.
M. P. Shurygina, N. O. Druzhkov, M. V. Arsen’ev, M. P. Bubnov, G. K. Fukin, S. A. Chesnokov, V. K. Cherkasov, Russ. J. Org. Chem., 2011, 47, 486.
V. B. Vol’eva, T. I. Prokofeva, A. I. Prokofev, I. S. Belostotskaya, N. L. Komissarova, V. V. Ershov, Russ. Chem. Bull., 1995, 44, 1720.
G. A. Abakumov, V. K. Cherkasov, T. N. Kocherova, N. O. Druzhkov, Yu. A. Kurskii, L. G. Abakumova, Russ. Chem. Bull., 2006, 55, 1195.
A. V. Piskunov, I. N. Meshcheryakova, G. K. Fukin, I. V. Smolyaninov, N. M. Khamaletdinova, O. V. Kuznetsova, Russ. J. Coord. Chem., 2014, 49, 205.
N. M. Khamaletdinova, I. N. Meshcheryakova, A. V. Piskunov, O. V. Kuznetsova, Russ. J. Struct. Chem., 2015, 56, 233.
A. V. Piskunov, I. N. Meshcheryakova, G. K. Fukin, I. V. Smolyaninov, N. T. Berberova, Russ. J. Coord. Chem., 2017, 43, 816.
M.-C. Corbeil, A. Beauchamp, Can. J. Chem., 1986, 64, 1876.
V. Singh, R. Chauhan, A. Kumar, L. Bahadur, N. Singh, Dalton Trans., 2010, 39, 9779.
M. K. Yadav, G. Rajput, A. N. Gupta, V. Kumar, M. G. B. Drew, N. Singh, Inorg. Chim. Acta, 2014, 421, 210.
G. A. Abakumov, V. K. Cherkasov, A. V. Piskunov, I. N. Meshcheryakova, N. V. Somov, Dokl. Chem., 2011, 440, 273.
A. V. Piskunov, I. N. Meshcheryakova, I. V. Smolyaninov, G. K. Fukin, V. K. Cherkasov, G. A. Abakumov, Russ. Chem. Bull., 2013, 62, 147.
S. S. Batsanov, Russ. J. Inorg. Chem., 1991, 36, 1694.
A. J. Gordon, R. A. Ford, The Chemist Companion, Wiley, New York, 1972.
V. A. Garnov, V. I. Nevodchikov, L. G. Abakumova, G. A. Abakumov, V. K. Cherkasov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 1728.
L. G. Makarova, A. N. Nesmeyanov, Metody elementoorganicheskoi khimii. Rtut’ [Methods of Organoelement Chemistry. Mercury], Nauka, Moscow, 1965, 438 pp. (in Russian).
Agilent (2018), CrysAlis Pro, Agilent Technologies Ltd, Yarnton, Oxfordshire, England, 2018.
G. M. Sheldrick, Acta Crystallogr., 2015, C71, 3.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0049–0060, January, 2020.
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Druzhkov, N.O., Meshcheryakova, I.N., Cherkasov, A.V. et al. New functionalized ditopic redox-active hydroxy-p-iminoquinone-type ligands and mercury(ii) complexes based on these ligands. Russ Chem Bull 69, 49–60 (2020). https://doi.org/10.1007/s11172-020-2722-x
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DOI: https://doi.org/10.1007/s11172-020-2722-x