Abstract
New copper(II), cobalt(II), and nickel(II) complexes with 1-[4-(phenydiazenyl)phenyldiazenyl]-naphthalen-2-ol and 1-[4-methyl-2-(4-methylphenyldiazenyl)phenyldiazenyl]naphthalen-2-ol have been synthesized by chemical and electrochemical methods and characterized by IR, 1H NMR, and X-ray absorption spectroscopy, as well as by magnetochemistry and quantum chemical calculations. Coordination of the nitrogen atom in the additional azo group to the metal ion is determined by its position (ortho or para) and metal nature.
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Comprehensive Coordination Chemistry II, McCleverty, Y.A. and Meyer, T.J., Eds., Amsterdam: Elsevier, 2004.
Bhunia, P., Sardar, D., Sarker, K.K., Ray, U.S., Ray, J.-S., Wu, J.S., Lu, T.-H., and Sinha, C., J. Coord. Chem., 2009, vol. 62, p. 552. DOI: 10.1080/00958970802291282.
Nandi, S., Bannerjee, D., Wu, J.-S., Lu, T.-H., Slawin, A.M.Z., Woolins, J.D., Ribas, J., and Sinha, C., Eur. J. Inorg. Chem., 2009, no. 26, p. 3972. DOI: 10.1002/ejic.200900423.
Porai-Koshits, B.A., Azokrasiteli (Azo Dyes), Leningrad: Khimiya, 1972.
Kondil, S.S., Transition Met. Chem., 1998, vol. 23, p. 461. DOI: 10.1023/A:1006900923122.
Daniel, J.W., Toxicol. Appl. Pharmacol., 1962, vol. 4, p. 572.
Broekaert, J.A. and Hörmann, P.K., Anal. Chim. Acta, 1981, vol. 124, p. 421. DOI: 10.1016/S0003-2670(01)93591-3.
Kurtoglu, M., Birbicer, N., Kimyonsen, U., and Serin, S., Dyes Pigm., 1999, vol. 41, p. 143.
Sato, O., Tao, J., and Zhang, Y.-Z., Angew. Chem. Int. Ed., 2007, vol. 46, p. 2152. DOI: 10.1002/anie.200602205.
Ire, M., Chem. Rev., 2000, vol. 100, no. 5, p. 1683. DOI: 10.1021/cr980068l.
Delaire, J.A. and Nakatani, K., Chem. Rev., 2000, vol. 100, no. 5, p. 1817. DOI: 10.1021/cr980078m.
Lee, S.H., Kim, S.K., Bok, J.H., Yoon, J., Lee, K., and Kim, J.S., Tetrahedron Lett., 2005, vol. 46, no. 47, p. 8163. DOI: 10.1016/jtetlet.2005.09.117.
Sarker, K.K., Sardar, D., Suwa, K., Otsuki, J., and Sinha, C., Inorg. Chem., 2007, vol. 46, no. 20, p. 8291. DOI: 10.1021/ic7012073.
Synthetic Coordination and Organometallic Chemistry, Garnovskii, A.D. and Kharisov, B.I., Eds., New York: Marcel Dekker, 2003.
Garnovskii, A.D. and Vasil’chenko, I.S., Russ. Chem. Rev., 2005, vol. 74, no. 3, p. 193. DOI: 10.1070/RC2005v074n03ABEH001164.
Kogan, V.A. and Shcherbakov, I.N., Ros. Khim. Zh., 2004, vol. 48, no. 1, p. 69.
Burlov, A.S., Nikolaevskii, S.A., Vasil’chenko, I.S., Koshchienko, Y.V., Uraev, A.I., Sennikova, E.V., Borodkin, G.S., Garnovskii, A.D., Minkin, V.I., Bogomyakov, A.S., Vlasenko, V.G., and Garnovskii, D.A., Russ. J. Coord. Chem., 2009, vol. 35, no. 7, p. 486.
Garnovskii, A.D., Burlov, A.S., Metelitsa, A.V., Vasil’chenko, I.S., Nikolaevskii, S.A., Borodkina, I.G., Minkin, V.I., Starikov, A.G., and Bezugliy, S.O., Russ. J. Coord. Chem., 2010, vol. 36, no. 7, p. 479.
Gütlich, P., Garcia, Y., and Wolke, T., Coord. Chem. Rev., 2001, vols. 219–221, p. 839. DOI: 10.1016/S0010- 8545(01)00381-2.
Wang, P., Ming, H., Zhang, J.Y., Liang, Z.C., Lu, Y.H., Zhang, Q.J., Xie, J.P., and Tian, Y.P., Opt. Commun., 2002, vol. 203, p. 159. DOI: 10.1016/S0030-4018(02) 01098-2
Weber, B., Coord. Chem. Rev., 2009, vol. 253, p. 2432. DOI: 10.1016/jccr.2008.10.002.
Burlov, A.S., Mashchenko, S.A., Nikolaevskii, S.A., Uraev, A.I., Korshunova, E.V., Antsyshkina, A.S., Sadikov, G.G., Sergienko, V.S., Kiskin, M.A., Vlasenko, V.G., Zubavichus, Ya.V., Garnovskii, D.A., and Levchenkov, S.I., Russ. J. Coord. Chem., 2013, vol. 39, no. 12, p. 813. DOI: 10.7868/S0132344X13120013.
Burlov, A.S, Mashchenko, S.A., Vlasenko, V.G., Zubavichus, Y.V., Uraev, A.I., Lyssenko, K.A., Levchenkov, S.I., Vasilchenko, I.S., Garnovskii, D.A., and Borodkin, G.S., J. Mol. Struct., 2014, vol. 1061, p. 47. DOI: 10.1016/jmolstruc.2013.12.007.
Yamamoto, T., X-Ray Spectrom., 2008, vol. 37, p. 572. DOI: 10.1002/xrs.1103.
Chernyshov, A.A., Veligzhanin, A.A., and Zubavichus, Y.V., Nucl. Instrum. Methods Phys. Res., Sect. A, 2009, vol. 603, p. 95. DOI: 10.1016/jnima.2008.12.167.
Kochubey, D.I., Babanov, Yu.A., Zamaraev, K.I., Vedrinskii, R.V., Kraizman, V.L., Kulipanov, G.N., Mazalov, L.N., Skrinskii, A.N., Fedorov, V.K., Khel’mer, B.Yu., and Shuvaev, A.T., Rentgenospektral’nyi metod izucheniya struktury amorfnykh tel: EXAFS-spektroskopiya (X-Ray Spectroscopy for Studying the Structure of Amorphous Materials: EXAFS Spectroscopy), novosibirsk: Nauka, Sib. Otd., 1988.
Newville, M., J. Synchrotron Radiat., 2001, vol. 8, p. 96. DOI: 10.1107/S0909049500016290.
Zabinski, S.I., Rehr, J.J., Ankudinov, A., and Alber, R.C., Phys. Rev. B, 1995, vol. 52, p. 2995. DOI: 10.1103/PhysRevB.52.2995.
Allen, F.H., Acta Crystallogr., Sect. B, 2002, vol. 58, p. 380. DOI: 10.1107/S0108768102003890.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision C 02, Wallingford CT: Gaussian, 2004.
Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, no. 2, p. 785. DOI: 10.1103/PhysRevB.37.785.
Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. DOI: 10.1063/1.464913.
Ditchfield, R., Hehre, W.J., and Pople, J.A., J. Chem. Phys., 1971, vol. 54, no. 2, p. 724. DOI: 10.1063/1.1674902.
Nivorozhkin, A.L., Toftlund, H., Nivorozhkin, L.E., Kamenetskaya, I.A., Antsishkina, A.S., and Porai-Koshits, M.A., Transition Met. Chem., 1994, vol. 19, no. 3, p. 319. DOI: 10.1007/BF00139103.
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Original Russian Text © A.S. Burlov, S.A. Mashchenko, V.G. Vlasenko, E.D. Garnovskaya, Ya.V. Zubavichus, S.I. Levchenkov, Yu.S. Kurinnaya, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 10, pp. 1708–1717.
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Burlov, A.S., Mashchenko, S.A., Vlasenko, V.G. et al. Chemical and electrochemical synthesis, local atomic structure, and properties of copper(II), cobalt(II), and nickel(II) complexes with azo compounds containing an additional azo group in the para or ortho position of the amine fragment. Russ J Gen Chem 85, 2338–2347 (2015). https://doi.org/10.1134/S1070363215100199
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DOI: https://doi.org/10.1134/S1070363215100199