Abstract
1,3-Dicarbonyl compounds were synthesized by the reaction of 9,10-phenanthrenequinone with acetylacetone and acetoacetic ester followed by the reduction and were characterized by spectroscopic and quantum-chemical methods. In the crystalline state and in solution, these compounds were found to exist in the keto form. The molecular and crystal structure of the binuclear lantern-type copper(II) carboxylate complex Cu2[μ2-OOCCH2(C14H8)(CO)2OC2H5]4(NCCH3)2, which was formed through the oxidation of the starting 1,3-dicarbonyl compound upon the complexation, was determined by X-ray diffraction. The coordination polyhedron of each copper atom can be described as a (4 + 1) square pyramid with four O atoms of four carboxyl groups at the base and the acetonitrile N atom in the apical position. The formation of the lantern-type dimer is attributed to the μ2-O,O' bidentate-bridging coordination mode of carboxyl groups.
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REFERENCES
W. Zhong-Yi, L. Bin, Z. Jue-Wen, et al., Org. Electron. 52, 89 (2018).
E. Anupama, H. Si Hyun, J. Thaksen, et al., J. Mater. Chem. C 6 (8), 2077 (2018).
G. Ma-Yong, L. Jian-Quan, and W. Xiang-Shan, Tetrahedron 73 (31), 4698 (2017).
A. Javid, A. Khojastehnezhad, and A. J. L. Pombeiro, Russ. J. Gen. Chem. 87 (12), 3000 (2017).
S. Bahadur, S. Khodia, and A. Patra, Chem. Commun. 54, 786 (2018).
Yu. N. Tkachenko, L. D. Popov, A. F. Pozharskii, et al., Russ. J. Org. Chem. 53 (10), 1564 (2017).
P. F. M. Oliveira, N. Haruta, A. Chamayou, et al., Tetrahedron 73 (16), 2305 (2017).
T. Fukushima, W. Drisdell, J. Yano, et al., J. Am. Chem. Soc. 137 (34), 10926 (2015).
S. P. J. T. Bachollet, D. Volz, B. Fiser, et al., Chem. Eur. J. 22 (35), 12430 (2016).
D. S. Kopchuk, N. V. Chepchugov, A. F. Khasanov, et al., Tetrahedron Lett. 57 (34), 3862 (2016).
G. V. Gridunova, Yu. T. Struchkov, R. V. Linko, et al., Russ. Chem. Bull. 41 (7), 1214 (1992).
G. V. Gridunova, V. E. Shklover, Yu. T. Struchkov, et al., Kristallografiya 33 (2), 390 (1988).
P. Smith-Verdier, F. Florencio, and S. Garcia-Blanco, Cryst. Struct. Commun. 9, 578 (1980).
R. V. Linko, V. K. Bel’sky, A. V. Varlamov, et al., Russ. Chem. Bull., Int. Ed. 50 (9), 1625 (2001).
H. Junek, H. Hamböck, and B. Hornischer, Monatsh. Chem. 98 (2), 315 (1967).
N. G. Kandile and T. M. Abdel-Latif, Acta Chim. Hungarica 126, 271 (1989).
A. C. Cope, L. Field, D. W. H. MacDowell, and M. E. Wright, J. Am. Chem. Soc. 78, 2547 (1956).
A. C. Cope and D. W. H. MacDowell, J. Am. Chem. Soc. 80, 5513 (1958).
T. G. G. Battye, L. Kontogiannis, O Johnson, et al., Acta Crystallogr. D 67, 271 (2011).
P. R. Evans, Acta Crystallogr. D 62, 72 (2006).
G. M. Sheldrick, Acta Crystallogr. C 71, 3 (2015).
A. D. Becke, J. Chem. Phys. 98, 5648 (1993).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37, 785 (1988).
P. J. Stephens, F. J. Devlin, C. F. Chabalowski, and M. J. Frisch, J. Phys. Chem. 98, 11623 (1994).
A. Schaefer, C. Huber, and R. Ahlrichs, J. Chem. Phys. 100, 5829 (1994).
E. D. Glendening, J. K. Badenhoop, A. E. Reed, et al., NBO 5.G. (Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2004). http://www.chem.wisc.edu/~nbo5.
Granovsky A., Firefly version 7.1.G. http://classic.chem.msu.su/gran/firefly/index.html.
S. E. Nefedov, E. V. Kushan, M. A. Yakovleva, et al., Russ. J. Coord. Chem. 38 (3), 224 (2012).
V. M. Rao, D. N. Sathyanarayana, and H. Manohar, J. Chem. Soc., Dalton Trans., No. 10, 2167 (1983).
E. V. Karpova, A. I. Boltalin, M. A. Zakharov, et al., Z. Anorg. Allg. Chem. 624, 741 (1998).
T. O. Denisova, E. V. Amel’chenkova, I. V. Pruss, et al., Russ. J. Inorg. Chem. 51 (7), 1020 (2006).
V. V. Goncharuk, G. L. Kamalov, G. A. Kovtun, et al., Catalysis. Cluster Approaches, Mechanisms of Heterogeneous and Homogeneous Catalysis (Kiev, Naukova Dumka, 2002) [in Russian].
Funding
The X-ray diffraction measurements were performed using unique equipment at the Kurchatov Synchrotron Radiation Source of the National Research Centre “Kurchatov Institute” and were supported by the Ministry of Education and Science of the Russian Federation (unique identifier of the project RFMEFI61917X0007). The publication was prepared with the support of the PFUR “5-100” Program.
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Translated by T. Safonova
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Linko, R.V., Ryabov, M.A., Polyanskaya, N.A. et al. Synthesis and Structures of 1,3-Dicarbonyl Compounds Based on 9,10-Phenanthrenequinone. Crystal and Molecular Structure of the Lantern-Type Binuclear Copper(II) Complex Cu2[μ2-OOCCH2(C14H8)(CO)2OC2H5]4(NCCH3)2. Crystallogr. Rep. 64, 887–893 (2019). https://doi.org/10.1134/S1063774519060129
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DOI: https://doi.org/10.1134/S1063774519060129